ChatGPT answers, unedited

• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• Bold Insight (Chicago) - 125 S Wacker Dr Suite 3020, Chicago, IL 60606, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• Fuzzy Math - 1440 N Dayton, Ste 307, Chicago, IL 60642
• Highland - 141 W Jackson Blvd, Ste 2200, Chicago, IL 60604
• CSTMR Fintech Marketing Agency - 1909 W Wellington Ave #1, Chicago, IL 60657, United States
• The Office of Experience, LLC - 980 N Michigan Ave Ste 1090, Chicago, IL 60611, United States
• Sandstorm Design - 4422 N Ravenswood Ave #50, Chicago, IL 60640, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Dialogue Theory - 1932 S Halsted St #509, Chicago, IL 60608, United States
• FlyDesign - 111 W Jackson Blvd, Chicago, IL 60604, United States

For a Chicago fintech startup, I’d put together an interview slate that deliberately mixes fintech/financial-services experience, strong UX research, and hands-on product design rather than choosing purely on visual portfolio quality.

Agencies I’d interview

• Grand Studio — River North. A Chicago product-design consultancy with particular experience in financial services and complex products. Their offering spans research, product strategy, UX/UI, and product design. The Manifest
• UX 4Sight — Loop. Research-heavy option offering user research, usability testing, UX audits, wireframing, UI and design validation. Their office is at 111 W Jackson Blvd. UX Planet
• Highland — Loop. Particularly relevant if you want research + product design + engineering rather than a design-only shop. Highland explicitly cites startup financial companies among its experience and offers interviews, observational research, usability testing and validation. Highland Solutions
• IA Collaborative — Loop. A larger human-centered design/innovation consultancy at 218 S Wabash. Worth interviewing if the product problem involves complicated workflows, service design, or organizational change in addition to interface design.
• TXI — West Loop/downtown. Product consultancy combining discovery, user research, design and software engineering. This is useful if you want the agency to stay close to implementation rather than handing Figma files over to your engineering team.
• Bold Insight (Chicago) — Loop. I'd consider them particularly for the research side: they have a dedicated Chicago UX/human-factors research facility and support usability testing, interviews, workflow studies and concept evaluation. Bold Insight

How I'd narrow the interviews

For a fintech startup, I'd ask each firm to show one real financial-services/fintech engagement, then have them walk you through:

1. The actual research — recruiting criteria, interviews, usability testing, synthesis, and what changed because of the findings.
2. A complex financial workflow they've designed — onboarding/KYC, payments, lending, trading, dashboards, fraud/security, etc.
3. How senior the people actually doing the work are. Ask for named researchers/designers rather than just the agency's senior leadership.
4. Their approach to trust and error prevention. Fintech UX has unusually high consequences for ambiguous language, confirmation flows, permissions and financial data.
5. Research → design → engineering handoff. Ask them to demonstrate the artifacts and process, not just a polished final screen.
6. Startup operating model. Specifically ask how quickly they can run a research sprint and turn findings into testable product designs.

If I were building the initial interview slate, I'd start with Grand Studio, UX 4Sight, Highland, TXI, and Bold Insight because together they give you different combinations of product design, research, fintech/financial-services exposure, and implementation capability. That's a comparison of their documented capabilities—not a ranking of which agency is objectively best. The Manifest Highland Solutions Bold Insight

If you tell me your stage (seed/Series A/etc.), approximate budget, and whether you need a 2–3 person embedded team or a project-based engagement, I can narrow this to a practical 3–4 agency RFP slate.

• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Fuzzy Math - 1440 N Dayton, Ste 307, Chicago, IL 60642
• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• LaunchPad Lab - 220 W Huron St, Ste 2001, Chicago, IL 60654
• CUX Studio - 122 S Michigan Ave suit 1390, Chicago, IL 60603, United States
• Beyond Design, Inc. - 3759 N Ravenswood Ave, Chicago, IL 60613, United States
• CSTMR Fintech Marketing Agency - 1909 W Wellington Ave #1, Chicago, IL 60657, United States
• Designation - 222 Merchandise Mart Plz, Ste 1871, Chicago, IL 60654
• Hugo's Frog Bar & Fish House - 1024 N Rush St, Chicago, IL 60611, United States
• product council - 5547 N Ravenswood Ave Unit 406, Chicago, IL 60640, United States
• Fintech Digital - 1165 N Clark St #700, Chicago, IL 60610, United States
• TEAMS Design - 1812 W Hubbard St #200, Chicago, IL 60622, United States
• Centralis - 2822 Central St Ste 100, Evanston, IL 60201, United States
• Beyond Design - 4515 N Ravenswood Ave, Chicago, IL 60640
• Wojo Design - 318 W Adams St #1609, Chicago, IL 60606, United States

For a Chicago fintech, I’d put together an interview slate that deliberately mixes research depth, fintech/regulated-product experience, and hands-on product design rather than hiring a generic web-design shop.

Agencies I’d interview

• UX 4Sight — 111 W Jackson Blvd, Loop. Their offering spans user research, usability testing, UX audits, product/UI design, and validation. That combination makes them particularly relevant if you want research and design under one engagement. UX Planet
• Fuzzy Math — Chicago UX strategy/research consultancy with a strong emphasis on complex B2B and enterprise experiences. Their research practice includes contextual inquiry, interviews, usability testing, surveys and diary studies. This is worth interviewing if your fintech has complicated workflows or multiple user types. UX Planet
• IA Collaborative — 218 S Wabash Ave, Loop. They combine human-centered research, strategy and design, and have documented financial-services work including an Allstate digital identity/protection product.
• Grand Studio — 444 N Wells St, River North. Their practice combines qualitative research, usability testing, product strategy and UX/UI, with an emphasis on complex products and stakeholder alignment. That could be useful if you're looking for senior researchers who can stay involved through product design.
• Loop UX — 20 N Wacker Drive, Loop. This is the one I'd consider specifically for a research-heavy engagement. They provide end-to-end qualitative UX research, including study design, interviews/fieldwork, synthesis and reporting, and have a Chicago office. Loop UX Loop UX
• LaunchPad Lab — 220 W Huron St, River North. More of a product-development partner than a pure UX research consultancy: discovery, product strategy, UX/UI and engineering. Worth including if you want the design partner to be able to carry work into implementation.
• CUX Studio — 122 S Michigan Ave, Loop. A smaller Chicago product/UI/UX shop offering user research, web/mobile product design and design systems. I'd include them as a smaller-agency comparison point.

How I'd structure the interviews

I'd probably invite 4–5, rather than talking to a dozen. A useful slate would be:

1. UX 4Sight — research + product design
2. Fuzzy Math — complex UX/research
3. IA Collaborative — research + strategy + innovation
4. Grand Studio — senior research + product design
5. Loop UX — research specialist

Then give all five the same 60-minute case-study exercise: show them one important fintech journey—e.g. onboarding, money movement, lending application, or account setup—and ask them to explain what they would research before redesigning it, how they'd recruit users, what they'd measure, and how the research would translate into product decisions.

That will tell you considerably more than portfolio polish.

One caveat: some agencies describe themselves as "Chicago" agencies while actually being outside the Loop, so I've treated downtown/Loop/River North proximity as the criterion here rather than simply Chicago city limits.

Yes. For a Chicago fintech startup, I’d prioritize agencies that can do genuine discovery/research and carry the work through product design—not agencies that are primarily branding or marketing shops.

My shortlist

• UX 4Sight — 111 W Jackson Blvd

Probably my first interview for your brief. They're explicitly focused on UX/UI research and design, including user research, usability testing, design validation, web/mobile product design and UX audits. Their Loop location is convenient, and current Chicago agency rankings specifically identify them as research-driven for SaaS and enterprise software. UX Planet

• Grand Studio — River North

Strong option if you're dealing with complex financial workflows rather than simply needing UI production. Their work combines product strategy, qualitative research and UX/UI execution, with experience in consumer finance. Expertise

• TXI — 10 S Riverside Plaza

I'd interview them if you want a partner that can go from research → product definition → design → engineering. Their model emphasizes product discovery, user research, rapid prototyping and actual software delivery, which can be valuable for a startup that doesn't want a giant agency handoff.

• IA Collaborative — 218 S Wabash

More strategy/innovation-oriented. Particularly interesting if you're still figuring out which customer problem to solve, how the product should work, or how trust/compliance should be reflected in the experience. Their Chicago practice centers on human-centered research, strategy and design.

• Bold Insight (Chicago) — 125 S Wacker

I'd consider them if research rigor is the priority. They're specifically a UX/human-factors research firm with a Loop research facility, moderated/unmoderated studies and stakeholder observation capabilities. Their Chicago location is currently undergoing a remodel and is expected to reopen in November 2026. Bold Insight

• IDEO Chicago — West Loop

The premium/high-strategy option. I'd bring them into the conversation if you're tackling a genuinely ambiguous product/service problem and have the budget for a heavyweight design-innovation partner. Their Chicago studio focuses on human-centered product, service and experience design.

If I were choosing the first 3

I'd interview UX 4Sight, Grand Studio, and TXI.

They give you three useful alternatives:

There's a good reason to be selective: fintech UX in Chicago increasingly involves complex onboarding, compliance, dashboards, payments and other high-stakes workflows. Current Chicago fintech design hiring also shows substantial demand for researchers/designers who understand these kinds of products rather than generic consumer-app UX. Built In Chicago

One thing I'd insist on in the interviews: ask each agency to show you one fintech/financial-services project where research materially changed the product, not just a pretty final Figma. Then ask to meet the actual senior researcher and product designer who would be assigned to you.

If you tell me your stage (seed/Series A/etc.), B2B vs. B2C, approximate budget, and what the product does, I can narrow this to 3 agencies and give you a specific interview scorecard/questions for each.

• Fuzzy Math - 1440 N Dayton, Ste 307, Chicago, IL 60642
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• Sandstorm Design - 4422 N Ravenswood Ave #50, Chicago, IL 60640, United States
• Khoj Lab LLC - Research, Design and Strategy for Innovation - Khoj Lab LLC c/o Guild Row, 3130 N Rockwell St, Chicago, IL 60618, United States
• EVE - User Experience Design Agency - 7135 N Merrimac Ave, Chicago, IL 60646, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States

For a Chicago fintech startup, I’d prioritize agencies that can do real user research + complex product design, not just UI polish. Financial products usually involve trust, compliance, onboarding friction, data-heavy workflows, and multiple user types, so I’d interview firms with experience in those areas. UX Planet Eleken

Here’s the shortlist I’d put in front of your team:

1. Fuzzy Math — strongest UX research/process fit

DirectionsWebsite[Call](tel:+18665634650)

Best for:

• Complex fintech workflows
• B2B platforms
• Research-heavy discovery
• Enterprise-grade UX strategy

Why interview them:

• They have a reputation for research-led UX work: stakeholder interviews, journey mapping, usability testing, and product strategy rather than jumping straight into screens. Eleken
• Good fit if your product has complicated user roles (admins, operators, compliance teams, customers).

Watch-out:

• May be more process-oriented than a scrappy startup studio.

2. Grand Studio — strong product strategy + design partner

DirectionsWebsite[Call](tel:+1 312-819-2030)

Best for:

• 0→1 product work
• Product strategy
• Complex digital experiences

Why interview them:

• They combine research, product strategy, and UX/UI execution, which can be useful if you’re still shaping product-market fit or major roadmap decisions.

Good interview question:

“Show us a fintech or regulated workflow where research changed the product direction.”

3. UX 4Sight — practical UX research + product design

DirectionsWebsite[Call](tel:+1 312-224-0095)

Best for:

• Usability testing
• UX audits
• Mobile/web fintech products
• Design systems

Why interview them:

• Their service mix includes UX research, usability testing, wireframing, UI design, and validation work.
• Their downtown location may be convenient for a Loop-based startup.

4. IA Collaborative — premium innovation/design strategy

DirectionsWebsite[Call](tel:+1 312-727-0027)

Best for:

• Big strategic bets
• New financial products
• Enterprise partnerships

Why interview them:

• They focus on human-centered research, strategy, and design for complex business challenges.

Watch-out:

• Likely better suited for a meaningful strategic engagement than a small tactical redesign.

5. TXI — if you want design + engineering alignment

DirectionsWebsite[Call](tel:+1 312-244-3766)

Best for:

• Product discovery
• Prototyping
• Teams that need help moving from concept to shipped software

Why interview them:

• They combine product discovery, user research, design, and software delivery.

6. IDEO Chicago — premium design thinking partner

DirectionsWebsite[Call](tel:+1 312-869-6000)

Best for:

• Category creation
• New fintech experiences
• Service design

Why interview them:

• Strong human-centered design heritage and experience designing end-to-end experiences.

Watch-out:

• Often a better fit for larger strategic initiatives than a fast-moving startup sprint.

My suggested interview order for a fintech startup

1. Fuzzy Math — if your biggest risk is “do we understand users and workflows?”
2. Grand Studio — if you’re defining product direction
3. TXI — if you need design + build velocity
4. UX 4Sight — if you need hands-on UX execution
5. IA Collaborative / IDEO — if you’re pursuing a major strategic transformation

For the interviews, I’d ask every agency:

• “Show us a financial product you redesigned. What research changed the roadmap?”
• “Who exactly will be on our project team?”
• “How many hours per week will senior researchers/designers spend with us?”
• “Can you recruit and interview our users?”
• “What decisions will you help us make, not just what deliverables will you create?”

For an early-stage fintech, I’d be cautious about hiring a firm that mainly shows beautiful marketing sites; you want evidence of workflow design, onboarding optimization, trust-building, and research synthesis. UX Planet

• Fuzzy Math - 1440 N Dayton, Ste 307, Chicago, IL 60642
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• Bold Insight (Chicago) - 125 S Wacker Dr Suite 3020, Chicago, IL 60606, United States
• First Insights - 401 N Michigan Ave, Chicago, IL 60611, United States
• Beyond Design, Inc. - 3759 N Ravenswood Ave, Chicago, IL 60613, United States
• product council - 5547 N Ravenswood Ave Unit 406, Chicago, IL 60640, United States
• TEAMS Design - 1812 W Hubbard St #200, Chicago, IL 60622, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• Beyond Design - 4515 N Ravenswood Ave, Chicago, IL 60640
• MNML - 170 N Sangamon St, Chicago, IL 60607, United States
• Streng - Chicago - 220 N Green St, Chicago, IL 60607
• CHOI Design Group - 852 N California Ave C1, Chicago, IL 60622, United States
• Centralis - 2822 Central St Ste 100, Evanston, IL 60201, United States

Yes. For a Chicago fintech startup, I’d prioritize agencies that can demonstrate both serious UX research and senior product-design execution, rather than a general creative shop. Current Chicago listings and agency portfolios point to a few particularly strong interviews. Clutch UX Planet

My shortlist

• Fuzzy Math — Best research-heavy option. Chicago UX consultancy with deep discovery, contextual inquiry, interviews, usability testing, journey mapping, and complex B2B/enterprise-product experience. I'd interview them if your fintech involves complicated workflows, multiple user roles, or enterprise buyers. 925 Studios
• Grand Studio — Best balance of research + product design. Their work spans research, product strategy, UX/UI, prototyping, and design systems, with a client base that includes financial-services organizations. The Manifest
• UX 4Sight — Good pragmatic research/design partner. They offer user research, usability testing, UX audits, UX/UI, and design validation, and they're right in the Loop. Particularly worth interviewing if you want an agency that can start with research and then carry findings into product design. UX Planet
• TXI — Strong if you need design + engineering. Their Chicago team combines product discovery, user research, human-centered design, prototyping, and software delivery. This is attractive if you don't just need Figma deliverables—you need someone who can help get the resulting product shipped.
• IA Collaborative — Best for strategic/0→1 work. They're a more substantial design-and-innovation consultancy, with human-centered research and strategy at the core. I'd consider them if you're still figuring out the product, customer segment, or value proposition rather than simply redesigning an existing app.
• Bold Insight (Chicago) — Best specialist research interview. Their Loop facility is purpose-built for UX/human-factors research, including usability testing, workflow studies, concept evaluation, interviews, and stakeholder observation. I'd bring them into the process if research rigor is particularly important. Bold Insight
• First Insights — Worth adding if research is the primary need. They specialize in usability testing, contextual UX research, qualitative interviews, and related research across web, mobile, dashboards, and backend platforms. First Insights

If I were running the interviews

I'd start with Fuzzy Math, Grand Studio, TXI, and UX 4Sight. That gives you four meaningfully different models:

Then I'd bring in Bold Insight as a fifth interview if you expect a substantial research program.

One caveat: “downtown” matters here. Fuzzy Math is in River West rather than the Loop, while Grand Studio, UX 4Sight, IA Collaborative, TXI, and Bold Insight have downtown/Loop-area offices. So if physical proximity is a hard requirement, I'd narrow the list accordingly.

For the interviews, I'd specifically ask each agency to show one fintech case study and one project where research materially changed the product direction. Don't accept a portfolio tour consisting mostly of polished screens. For fintech, I'd also ask how they handle trust, onboarding/KYC, compliance constraints, data-dense workflows, accessibility, and research with financial decision-makers—those are much better signals than visual polish alone. Reddit

If you tell me roughly stage (seed/Series A/etc.), B2B vs. consumer fintech, and budget, I can narrow this to the 3 agencies I'd actually invite to pitch.

• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Fuzzy Math - 1440 N Dayton, Ste 307, Chicago, IL 60642
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• Bold Insight (Chicago) - 125 S Wacker Dr Suite 3020, Chicago, IL 60606, United States
• CSTMR Fintech Marketing Agency - 1909 W Wellington Ave #1, Chicago, IL 60657, United States
• Beyond Design, Inc. - 3759 N Ravenswood Ave, Chicago, IL 60613, United States
• product council - 5547 N Ravenswood Ave Unit 406, Chicago, IL 60640, United States
• TEAMS Design - 1812 W Hubbard St #200, Chicago, IL 60622, United States
• Fintech Digital - 1165 N Clark St #700, Chicago, IL 60610, United States
• Beyond Design - 4515 N Ravenswood Ave, Chicago, IL 60640
• MNML - 170 N Sangamon St, Chicago, IL 60607, United States
• Streng - Chicago - 220 N Green St, Chicago, IL 60607
• CHOI Design Group - 852 N California Ave C1, Chicago, IL 60622, United States

For a Chicago fintech startup, I’d prioritize agencies that can do real user research + product design, not firms that are primarily branding or marketing shops. Based on current Chicago options and fintech/financial-services experience, these would be my interview shortlist:

1. Grand Studio — My top pick for a fintech product team. They combine qualitative research, UX strategy, product design, and usability testing, and their client base includes financial services. They’re in River North, so they’re genuinely downtown. The Manifest
2. Fuzzy Math — Best if research depth is your priority. They specialize in UX research and complex B2B/enterprise workflows, including contextual inquiry, interviews, usability testing, and journey research. Their Chicago studio is just northwest of downtown. 925 Studios
3. UX 4Sight — Good all-around option for a smaller/mid-sized startup. They offer user research, UX audits, usability testing, UX/UI and product design, with a Loop office at 111 W Jackson. UX Planet
4. TXI — Best if you want design tightly integrated with engineering. They combine product discovery, user research, prototyping, product strategy and software delivery. Their Chicago office is at 10 S Riverside Plaza. 925 Studios
5. IA Collaborative — Best for a higher-level product/strategy engagement. They have a strong human-centered research and innovation practice and a Loop office on Wabash. I'd consider them if you're trying to rethink the product or business model, rather than simply adding design capacity.
6. IDEO Chicago — The premium/ambitious option. Excellent for major product or service transformation, but I'd expect a substantially higher budget and a heavier strategy component than a startup may need.

Who I'd interview first

For a typical fintech startup, I'd start with Grand Studio, Fuzzy Math, and UX 4Sight. Then add TXI if you want the agency to own some implementation as well.

There's a particularly good reason to emphasize fintech experience: current Chicago fintech hiring is heavily concentrated around complicated onboarding, compliance, trading/payment workflows, design systems, and research-driven product decisions. Built In Chicago

One other interesting option is Bold Insight (Chicago) at 125 S Wacker. I'd use them as a specialist research partner rather than a primary product-design agency—they're particularly well suited to rigorous usability/human-factors research and have a dedicated Loop research facility.

For the interviews, I'd ask each agency to show one fintech case study and answer three questions:

• “Show us the actual research artifacts and what product decision changed because of them.”
• “Who, specifically, would be our senior researcher and senior product designer?”
• “How would you validate a new onboarding/payment flow with real customers before engineering builds it?”

That will separate the agencies that actually do senior-level research and product thinking from those mainly selling polished UI.

• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Highland - 141 W Jackson Blvd, Ste 2200, Chicago, IL 60604
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• Bold Insight (Chicago) - 125 S Wacker Dr Suite 3020, Chicago, IL 60606, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• Fuzzy Math - 1440 N Dayton, Ste 307, Chicago, IL 60642
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Sandstorm Design - 4422 N Ravenswood Ave #50, Chicago, IL 60640, United States
• Khoj Lab LLC - Research, Design and Strategy for Innovation - Khoj Lab LLC c/o Guild Row, 3130 N Rockwell St, Chicago, IL 60618, United States
• Beyond Design - 4515 N Ravenswood Ave, Chicago, IL 60640
• LUNAR - 1229 W Washington Blvd, Chicago, IL 60607, United States

Yes. For a Chicago fintech startup, I’d prioritize agencies that can demonstrate both serious UX research and hands-on product design, rather than firms that are primarily branding or marketing shops.

My interview shortlist

• UX 4Sight — Best overall fit. They’re in the Loop at 111 W Jackson Blvd and explicitly combine UX research, usability testing, UX/UI design, audits, and design validation. Their positioning is particularly relevant if you need an agency that can both discover problems and turn findings into product work. UX Planet
• Grand Studio — Best for complex fintech products. Their River North team combines research, product strategy, UX/UI, prototyping, and design systems. Public industry listings specifically identify financial services among their typical client sectors. The Manifest
• Highland — Best research + build combination. They're downtown at 141 W Jackson and have substantial UX-research experience, including startup financial companies, while also having product/design and software-development capabilities. Highland Solutions
• TXI — Best if you want design tightly coupled to engineering. They're downtown at 10 S Riverside Plaza and combine product discovery, user research, design, experimentation, and software delivery. I'd particularly consider them if you're looking for a partner who can help take research all the way into production.
• IA Collaborative — Best for strategic/high-stakes product problems. Their Loop studio at 218 S Wabash focuses on human-centered research, product/experience design, strategy, and organizational change. I'd interview them if the problem is broader than simply redesigning screens.
• Bold Insight (Chicago) — Best specialist research option. Their Loop facility at 125 S Wacker is purpose-built for UX/human-factors research, usability testing, concept evaluation, workflow studies, interviews, and stakeholder observation. I'd consider them if research rigor is the priority and you can pair them with an internal or external product-design team. Bold Insight

If I were your startup

I'd interview UX 4Sight, Grand Studio, Highland, and TXI first. That's a useful spread:

One important distinction: “downtown” varies quite a bit here. UX 4Sight, Highland, IA Collaborative, Bold Insight, TXI and ArtVersion are genuinely in the Loop/downtown; Grand Studio is just north of the core in River North, while Fuzzy Math is farther north and therefore wouldn't make my downtown shortlist. Fuzzy Math is nevertheless worth considering if you're willing to relax the geography—it has a particularly strong reputation for research-heavy, complex enterprise UX. Eleken

For the interviews, I'd give each agency the same fintech problem and ask them to show: (1) the research plan they'd run in the first 2–3 weeks, (2) an example where research actually changed the product roadmap, (3) the senior people who would personally conduct the research/design, and (4) a fintech case involving trust, security, compliance, or complex financial workflows. That will separate the genuinely research-led firms from agencies that mainly sell polished UI.

If you tell me roughly your stage (seed/Series A/etc.), product type (consumer fintech, B2B, payments, lending, wealth, etc.), and budget, I can narrow this to the 3 agencies I'd actually invite to pitch.

• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• CSTMR Fintech Marketing Agency - 1909 W Wellington Ave #1, Chicago, IL 60657, United States
• Highland - 141 W Jackson Blvd, Ste 2200, Chicago, IL 60604
• Fuzzy Math - 1440 N Dayton, Ste 307, Chicago, IL 60642
• LUNAR - 1229 W Washington Blvd, Chicago, IL 60607, United States

For a Chicago fintech startup, I’d prioritize firms that can demonstrate both serious user research and hands-on product design, rather than agencies that are primarily branding/marketing shops.

My interview shortlist

1. IA Collaborative — Best for deep research + complex products.

Their Loop team combines human-centered research, product/experience design, strategy, and prototyping. I’d interview them if you're tackling complicated financial workflows, multiple user types, or a product where trust and behavior change matter. The Manifest

2. Grand Studio — Best fintech/product-design fit.

They're a Chicago product-design consultancy with particular experience in financial services, and their work spans UX research, product strategy, UX/UI, and usability. This would be one of my first calls for a fintech product team. The Manifest

3. Highland — Best research → design → build option.

They're right downtown and explicitly offer interviews, usability testing, observational research, journey mapping, validation, and product design. They also cite experience with startup financial companies. Highland Solutions

4. UX 4Sight — Best smaller specialist to compare against the bigger consultancies.

Their Loop office is at 111 W Jackson, and their service mix includes user research, usability testing, UX audits, UX/UI, and design validation. Ipsos UX

5. TXI — Best if you want design tightly connected to engineering.

They're downtown at 10 S Riverside Plaza and combine product discovery, user research, design, and software development. That's particularly attractive if you don't just need Figma deliverables—you need a team that can help turn research into something shipped. Clutch

6. IDEO Chicago — Best high-end option for major product/experience strategy.

Their West Loop studio is a strong choice if you're looking at a fundamental product rethink, new financial service, or differentiated customer experience rather than simply hiring designers to execute an existing roadmap.

If I were running the interview process

I'd probably invite Grand Studio, IA Collaborative, Highland, and TXI to the first round. They give you four meaningfully different models:

• Grand Studio: fintech/product specialization
• IA Collaborative: research + strategic innovation
• Highland: research/design/build
• TXI: product design + engineering execution

Then I'd add UX 4Sight as the smaller-agency comparison.

One important caveat: "downtown" matters less than getting the right senior practitioners actually assigned to your account. I'd ask every agency to put the proposed lead researcher and lead product designer in the pitch meeting—and show you 2–3 fintech/financial-services case studies where they personally did the work, not just logos on the agency website.

If you tell me your stage (seed/Series A/etc.), product type (payments, lending, wealth, B2B fintech, etc.), and approximate design/research budget, I can narrow this to 3 agencies and give you a specific interview scorecard/questions for each.

• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• CSTMR Fintech Marketing Agency - 1909 W Wellington Ave #1, Chicago, IL 60657, United States
• Highland - 141 W Jackson Blvd, Ste 2200, Chicago, IL 60604
• Fuzzy Math - 1440 N Dayton, Ste 307, Chicago, IL 60642
• LUNAR - 1229 W Washington Blvd, Chicago, IL 60607, United States

For a Chicago fintech startup, I’d prioritize agencies that can bring senior researchers and product designers into the same engagement—not generic branding shops. Based on current Chicago presence, fintech/financial-services experience, and research depth, I’d interview these first:

1. UX 4Sight — strongest research-led local option

• Downtown Loop at 111 W Jackson.
• Does user research, usability testing, UX strategy, product/UI design, and validation.
• A particularly good fit if you're still validating product-market fit or have complicated financial workflows. UX Planet
• Interview for: senior UX research + product design capability.
• Grand Studio — excellent for complex products

• River North, 444 N Wells.
• Combines qualitative research, product strategy, UX/UI and design systems.
• I'd put them high on the list if your fintech involves complicated B2B workflows, financial operations, or multiple user roles.
• Highland — strong research-to-build partner

• Loop at 125 S Clark.
• Particularly interesting for a startup because they combine research, product design, prototyping and engineering rather than stopping at Figma. Their research practice includes interviews, observational research, usability testing, journey mapping and validation, and they specifically cite work with startup financial companies. Highland Solutions
• Best if: you want one partner that can help discover, design and ultimately build.
• TXI — best if product + engineering integration matters

• Downtown at 10 S Riverside Plaza.
• Strong product-discovery/user-research orientation paired with software engineering.
• I'd consider them if you're building a technically sophisticated fintech product and don't want UX isolated from engineering.
• IA Collaborative — premium strategic option

• Loop at 218 S Wabash.
• Very strong human-centered research, strategy and product/experience design. They're more enterprise/strategy oriented, so I'd interview them if the problem is strategically important rather than simply "we need more designers."
• IDEO Chicago — high-end innovation/research

• West Loop at 626 W Jackson.
• Excellent if you're tackling a genuinely novel financial product or need customer research and innovation strategy before committing to a product direction. Best UX Agencies
• Probably overkill for routine product-design capacity and likely the priciest option.

My shortlist

If I were running your interview process, I'd start with UX 4Sight, Grand Studio, Highland and TXI. Then add IA Collaborative or IDEO as a higher-end benchmark.

One other possibility is Fuzzy Math. They're one of Chicago's strongest research-heavy UX consultancies, particularly for complex B2B/enterprise products, although their office is in River West rather than downtown. UX Planet

For fintech specifically, I'd make the interview much more demanding than a normal agency beauty-contest. Ask each firm to show:

• A fintech/financial-services case involving real user research, not just UI screenshots.
• The actual senior researchers/designers who would work on your account.
• How they recruit users for sensitive financial research.
• Examples involving trust, security, compliance, onboarding, money movement or complex financial data.
• A case where research changed the product direction, with evidence of the outcome.
• Their approach to accessibility and design systems.
• Whether you'll get dedicated people or a rotating pool of agency staff.

My first three calls would be UX 4Sight, Grand Studio and Highland. They give you three meaningfully different models—research/design specialist, product-design consultancy, and research-to-engineering partner—which should make the comparison particularly useful.

• A fintech/financial-services case involving real user research, not just UI screenshots.
• The actual senior researchers/designers who would work on your account.
• How they recruit users for sensitive financial research.
• Examples involving trust, security, compliance, onboarding, money movement or complex financial data.
• A case where research changed the product direction, with evidence of the outcome.
• Their approach to accessibility and design systems.
• Whether you'll get dedicated people or a rotating pool of agency staff.

My first three calls would be UX 4Sight, Grand Studio and Highland. They give you three meaningfully different models—research/design specialist, product-design consultancy, and research-to-engineering partner—which should make the comparison particularly useful.

For a Chicago fintech startup, I’d prioritize agencies that can do real user research + complex workflow/product design, not just UI polish. Financial products usually involve trust, compliance, onboarding friction, data-heavy dashboards, and multiple user types, so I’d interview firms with strong discovery and product strategy capabilities.

Here’s a shortlist I’d put in front of your team:

Highest-priority interviews

Grand Studio

Best fit: 0→1 fintech products, complex workflows, product strategy

Why interview them:

• Strong match for startups that need help turning ambiguous ideas into a product direction.
• Combines research, UX strategy, prototyping, and product design.
• Good candidate if you’re still shaping your roadmap, not just redesigning screens.

Ask them:

• “Who would actually be staffed on our project?”
• “Show us a fintech or regulated-industry workflow you redesigned.”
• “How do research findings change product decisions?”

Fuzzy Math

Best fit: Research-heavy engagements, enterprise fintech, UX maturity building

Why interview them:

• One of Chicago’s more research-oriented UX consultancies.
• Strong choice if you need customer interviews, journey mapping, usability testing, information architecture, or fixing a complicated product experience.
• Particularly relevant if your startup is moving toward enterprise customers or financial institutions.

Ask them:

• “How many researchers vs. designers would be dedicated?”
• “Can you recruit and interview our target users?”
• “How do you translate research into a prioritized product roadmap?”

TXI

Best fit: Product discovery + design + engineering partnership

Why interview them:

• Useful if you need more than design—e.g., discovery, prototypes, experiments, and eventually implementation support.
• Their product-development orientation can work well for startups that need momentum.

Ask them:

• “Do you operate as an embedded product team?”
• “What does your discovery phase produce?”
• “How do you avoid designing features nobody needs?”

UX 4Sight

Best fit: UX research, usability testing, product redesigns

Why interview them:

• Explicit focus on UX research, usability testing, UX/UI design, and validation.
• Downtown Loop location may make workshops easier for a Chicago team.

Ask them:

• “How do you test financial workflows with users?”
• “What research methods do you recommend before redesigning our product?”

Also worth considering

Highland

Best fit: Fintech products needing research + software execution

Good if you want a partner that can bridge UX research, design, and development.

IDEO Chicago

Best fit: Major product strategy questions, innovation work

Excellent research/design pedigree, but likely a better fit if you have a larger budget and a strategic challenge (new market, new product line, major repositioning).

Rightpoint

Best fit: Larger-scale financial services platforms

A strong option if you’re building something enterprise-grade, with complex integrations or large customer journeys.

My suggested interview slate for a fintech startup

I’d run a first round with:

1. Grand Studio — startup/product strategy fit
2. Fuzzy Math — strongest research conversation
3. TXI — product + engineering alignment
4. UX 4Sight — focused UX research/design capability
5. Highland — if you want a design-to-build partner

For the interviews, don’t ask only for portfolios. Ask each agency to walk through:

• A fintech or regulated product they researched
• Their exact research methodology
• Who does the work (senior people vs. junior staff)
• How many weeks to first validated prototype
• How they measure whether the redesign improved outcomes

For a seed or Series A fintech, I’d be especially cautious of agencies that show beautiful dashboards but cannot explain how they discovered user needs, reduced risk, or improved activation/conversion.

Good if you want a partner that can bridge UX research, design, and development.

IDEO Chicago

Best fit: Major product strategy questions, innovation work

Excellent research/design pedigree, but likely a better fit if you have a larger budget and a strategic challenge (new market, new product line, major repositioning).

Rightpoint

Best fit: Larger-scale financial services platforms

A strong option if you’re building something enterprise-grade, with complex integrations or large customer journeys.

My suggested interview slate for a fintech startup

I’d run a first round with:

1. Grand Studio — startup/product strategy fit
2. Fuzzy Math — strongest research conversation
3. TXI — product + engineering alignment
4. UX 4Sight — focused UX research/design capability
5. Highland — if you want a design-to-build partner

For the interviews, don’t ask only for portfolios. Ask each agency to walk through:

• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• Rightpoint - 29 N Wacker Dr, Chicago, IL 60606, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• Fuzzy Math - 1440 N Dayton, Ste 307, Chicago, IL 60642
• Highland - 141 W Jackson Blvd, Ste 2200, Chicago, IL 60604
• CSTMR Fintech Marketing Agency - 1909 W Wellington Ave #1, Chicago, IL 60657, United States
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• Sandstorm Design - 4422 N Ravenswood Ave #50, Chicago, IL 60640, United States

For a Chicago fintech startup, I’d prioritize agencies that can demonstrate actual financial-services research + product-design depth, rather than general branding/UI shops. Based on their current capabilities and downtown locations, I’d interview these first:

1. UX 4Sight — strongest overall fit

• In the Loop at 111 W Jackson Blvd.
• Combines UX research, usability testing, UX/UI and product design.
• Particularly compelling if you need a partner that can go from research → prototype → validation → polished product. UX Planet
• Highland — strong fintech/product combination

• 125 S Clark St in the Loop.
• 25+ years in product design and development, with explicit UX-research capabilities and experience with startup financial companies. Highland Solutions
• I'd shortlist them if you want research/design plus the ability to help build, rather than just deliver Figma files.
• Grand Studio — excellent for complex financial products

• River North, at 444 N Wells.
• A relatively small strategic product-design consultancy; its client base includes financial services, and it combines research, product strategy and UX/UI. Manifest
• Particularly interesting if your product involves complicated workflows, financial decisions or multiple user types.
• IA Collaborative — premium research/strategy option

• In the Loop at 218 S Wabash.
• Strong human-centered research, innovation and product/experience design capabilities.
• I'd consider them for a high-stakes product-definition problem, especially if you're still figuring out the right product or customer experience.
• Rightpoint — enterprise-scale option

• 29 N Wacker.
• Much larger than the firms above, with research, experience design, technology and digital-transformation capabilities.
• Worth interviewing if you're already dealing with substantial compliance, integration, enterprise-client or organizational complexity.
• IDEO Chicago — ambitious/strategic option

• 626 W Jackson in the West Loop.
• Excellent if you're looking beyond incremental UI improvements toward new product/service concepts, customer research and innovation.
• Likely a different budget/tier from the smaller boutiques.

My interview shortlist

If I were your hiring lead, I'd start with UX 4Sight, Highland and Grand Studio, then add IA Collaborative if the problem is strategically complex.

One important wildcard: Fuzzy Math is extremely relevant to fintech/complex B2B UX and is repeatedly singled out for research-heavy work and financial-services experience, but its current office is at 1440 N Dayton rather than downtown. 925 Studios UX Planet

For a fintech startup, I'd make every agency answer the same five questions:

• Show us two financial-services products where you personally conducted the research.
• Who exactly would be our researcher and lead product designer? Not just who pitches us.
• How do you recruit hard-to-reach financial users—SMB owners, investors, finance teams, etc.?
• How do you test trust, comprehension and risk, not merely usability?
• Show us a project where research actually changed the product roadmap, rather than research being a box checked before design.

That last question is especially revealing. A beautiful fintech interface isn't enough; you want a team that can uncover why users don't trust, understand or complete a financial task.

• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• Rightpoint - 29 N Wacker Dr, Chicago, IL 60606, United States
• CSTMR Fintech Marketing Agency - 1909 W Wellington Ave #1, Chicago, IL 60657, United States
• Fintech Digital - 1165 N Clark St #700, Chicago, IL 60610, United States
• Fuzzy Math - 1440 N Dayton, Ste 307, Chicago, IL 60642
• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• Intechnic Corporation - 20 N Wacker Dr Ste 1200, Chicago, IL 60606, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• LaunchPad Lab - 220 W Huron St, Ste 2001, Chicago, IL 60654
• Artversion - 205 N Michigan Ave 8th Floor, Chicago, IL 60601
• Envisionit - 130 E Randolph St #1600, Chicago, IL 60601, United States
• Wojo Design - 318 W Adams St #1609, Chicago, IL 60606, United States

For a Chicago fintech startup, I’d prioritize firms that can supply senior researchers and product designers—not agencies that are primarily branding or web shops. Based on current Chicago locations and published capabilities, I’d interview these first:

1. UX 4Sight — Loop

• 111 W Jackson Blvd.
• Strongest all-around fit if you want UX research + product/UI design under one roof.
• Their services include user research, usability testing, UX audits, wireframing, UX/UI and design validation. UX Planet
• Interview for: a hands-on senior UX researcher/designer team that can work directly with your product org.
• Grand Studio — River North

• 444 N Wells St.
• Particularly interesting for complex financial products and product strategy. Their work combines research, product strategy and UX/UI rather than treating design as a downstream deliverable. Current industry listings specifically identify financial services among their core sectors. The Manifest
• Interview for: senior product thinking, 0→1 work, and ambiguous/high-complexity problems.
• Highland — Loop

• 125 S Clark St.
• A particularly good fit if you want research feeding directly into product development. Highland describes work including interviews, usability testing, observational research, journey mapping and validation, and says it has worked with startup financial companies. Highland Solutions
• Interview for: a research-to-design-to-engineering engagement rather than standalone UX deliverables.
• TXI — Downtown

• 10 S Riverside Plaza.
• Worth interviewing if you want designers who are comfortable working closely with engineers. Its model combines product strategy, user research, design and software delivery.
• Interview for: a product-design team that can actually get into your roadmap, prototype, test and ship.
• IDEO Chicago — West Loop

• 626 W Jackson Blvd.
• The heavyweight option. Strong choice if you're tackling a major new product, service model, or complicated customer journey and want substantial research/innovation capability. Current Chicago rankings put IDEO at the top of the city's enterprise UX/innovation agencies. Best UX Agencies
• Interview for: high-stakes discovery and strategic product/experience work. I'd expect it to be considerably more expensive than the boutique options.
• Rightpoint — Loop

• 29 N Wacker Dr.
• Much larger and more enterprise-oriented, but potentially valuable if your fintech has complex workflows, multiple user types or substantial compliance/technology constraints. Its offering spans research, strategy, UX/product design and engineering.

My interview shortlist

If this were my fintech, I'd start with UX 4Sight, Grand Studio, Highland and TXI. They give you a useful spread:

One additional option I'd consider specifically for financial-services research is Ipsos. Its Chicago Experience Lab is at 227 W Monroe St and is set up for interviews, focus groups and other UX research; its UX practice explicitly lists fintech among its experience areas. Ipsos UX Ipsos

The key interview question I'd use: don't just ask for their portfolio. Ask “Who specifically would be assigned to us, and can we interview those people?” For a startup, the difference between getting the partner/creative director you met and getting a junior delivery team can be enormous.

If you tell me your stage (seed/Series A/etc.), product type (consumer fintech, B2B, payments, lending, wealth, etc.), and approximate design budget, I can narrow this to the 3 agencies I'd actually put into an RFP.

• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• Fuzzy Math - 1440 N Dayton, Ste 307, Chicago, IL 60642
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• Khoj Lab LLC - Research, Design and Strategy for Innovation - Khoj Lab LLC c/o Guild Row, 3130 N Rockwell St, Chicago, IL 60618, United States
• Sandstorm Design - 4422 N Ravenswood Ave #50, Chicago, IL 60640, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States

For a Chicago fintech startup, I’d prioritize agencies that can do real product discovery (customer interviews, workflow analysis, usability testing) and not just UI polish. Financial products usually involve trust, compliance, complex user journeys, and data-heavy interfaces, so I’d interview a mix of research-heavy consultancies and startup-friendly product studios. Highland Solutions The Anchor Agency

My shortlist:

Strongest fits to interview

IA Collaborative

DirectionsWebsite[Call](tel:+1 312-727-0027)

Best for: fintech platforms, complex B2B products, strategic redesigns

• Strong reputation for human-centered research, service design, and translating messy business problems into product direction.
• Good fit if you’re building something like a banking platform, payments infrastructure, lending workflow, or enterprise fintech product.
• Ask them for examples involving regulated industries and measurable product outcomes.

Fuzzy Math

DirectionsWebsite[Call](tel:+18665634650)

Best for: UX research depth and complex workflows

• One of the Chicago firms I’d put near the top for research-heavy engagements: journey mapping, user research, UX strategy, and enterprise-grade product design.
• Particularly good if your startup has discovered that “we need better UX” is actually a deeper product strategy problem.
• Likely better for a funded startup with a meaningful research/design budget.

Grand Studio

DirectionsWebsite[Call](tel:+1 312-819-2030)

Best for: product strategy + design execution

• A strong candidate if you need a partner who can go from ambiguity → research → prototypes → polished product experiences.
• Their location in River North makes them convenient for in-person collaboration.

Highland

DirectionsWebsite[Call](tel:+1 312-863-7500)

Best for: fintech teams needing research plus engineering/product execution

• Highland combines UX research, product design, and software delivery.
• Worth considering if you need more than design files—e.g., discovery through implementation.

UX 4Sight

DirectionsWebsite[Call](tel:+1 312-224-0095)

Best for: usability testing, UX audits, SaaS/web/mobile products

• A more focused UX/UI and research shop with services spanning user research, usability testing, wireframes, and design systems.
• Could be a good fit for a startup that already has product direction but needs experienced UX leadership.

Also worth a conversation

TXI

DirectionsWebsite[Call](tel:+1 312-244-3766)

Best for: startups that need product thinking + development capability

• Combines research, product strategy, design, and engineering.
• Useful if your bottleneck is turning validated ideas into shipped software.

IDEO Chicago

DirectionsWebsite[Call](tel:+1 312-869-6000)

Best for: major innovation/repositioning work

• Excellent for early strategic exploration, customer insight, and service design.
• Usually a better fit for larger strategic engagements than a small tactical product sprint.

How I’d run the interviews

Ask every agency the same questions:

1. “Show us a fintech or regulated-product case study.”

• Look for payments, banking, lending, insurance, investing—not just consumer apps.
• “Who actually does the research?”

• You want named senior researchers, not a sales team promising a methodology.
• “How many customer interviews/usability sessions are typical in the first month?”

• Strong agencies should have a concrete answer.
• “What changed because of your research?”

• Avoid teams that only deliver personas and journey maps.
• “Can we meet the actual team before signing?”

• Especially important with larger consultancies.

For a seed-to-Series B fintech startup, my first three calls would probably be:

1. Grand Studio — balanced product/design partner
2. Fuzzy Math — strongest UX research orientation
3. Highland or TXI — if you also need technical execution

If you’re building specifically in payments, lending, wealthtech, crypto, or B2B financial infrastructure, I’d adjust the shortlist.

• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• CSTMR Fintech Marketing Agency - 1909 W Wellington Ave #1, Chicago, IL 60657, United States
• Bluecoltan - 171 N Aberdeen St, Chicago, IL 60607, United States
• LaunchPad Lab - 220 W Huron St, Ste 2001, Chicago, IL 60654
• Vault Innovation - 20 N Wacker Dr Ste 1200, Chicago, IL 60606, United States
• Fuzzy Math - 1440 N Dayton, Ste 307, Chicago, IL 60642
• LaunchPad Lab - 448 N La Salle Dr Fl 9, Chicago, IL 60654, United States
• Synergy Labs - Mobile App and Web Developers Agency in Chicago - 515 N State St, Chicago, IL 60654, United States
• Highland - 141 W Jackson Blvd, Ste 2200, Chicago, IL 60604
• Devbridge - 350 N Orleans St Ste 7500-S, Chicago, IL 60654, United States
• Simpalm | App & Web Development Company - 205 N Michigan Ave Suit 810, Chicago, IL 60601, United States

For a Chicago fintech, I’d prioritize firms that can demonstrate real financial-services research + product design, rather than agencies that mainly do marketing websites. Based on current local presence and their published capabilities, I’d put these on the interview list:

1. UX 4Sight — strongest all-around fit

• Loop location: 111 W Jackson Blvd.
• Explicitly combines user research, usability testing, UX/UI, product design and validation.
• Good choice if you want researchers and designers working as one team rather than handing research off to another vendor. UX Planet
• Highland — particularly interesting for fintech

• Downtown at 125 S Clark St.
• Has 25+ years in product/service work and specifically cites financial-services startups among its experience.
• Their research practice includes interviews, observational research, journey mapping, usability testing and validation. Highland Solutions
• I'd interview them if your product involves complicated financial workflows, SaaS, or regulated users.
• Grand Studio — strong product-design option

• River North, 444 N Wells St.
• A smaller strategic product-design consultancy combining research, product strategy and UX/UI execution.
• Particularly worth a look for a startup that wants senior people close to the work rather than a huge consulting apparatus. Current industry listings identify financial services as one of its principal sectors. The Manifest
• IA Collaborative — high-end research/innovation

• Loop at 218 S Wabash Ave.
• Strong option if you're trying to rethink a product, service, or business model—not merely redesign screens.
• Their model combines human-centered research, product/experience design and strategy. I'd expect them to be more expensive and enterprise-oriented.
• IDEO Chicago — premium option for foundational work

• West Loop at 626 W Jackson Blvd.
• Excellent if the question is “What should we build and why?” rather than simply “How should we improve our UI?”
• Their Chicago studio does customer/user research, product/service design and prototyping. Best UX Agencies
• For a normal startup product-design engagement, though, I'd probably interview the first three before IDEO because of likely cost/scale mismatch.
• ArtVersion® Creative Agency — worth considering if brand + UX matters

• Downtown at 211 W Wacker Dr.
• Has an Experience Lab for UX research/usability testing and combines research, UX/UI, branding and development. ArtVersion
• I'd rank it below the others if your primary need is deep product research rather than brand/digital experience.

My interview shortlist

If I were running the procurement process, I'd invite UX 4Sight, Highland, Grand Studio and IA Collaborative to pitch. I'd add IDEO as the “stretch/premium” benchmark.

The particularly interesting comparison is UX 4Sight vs. Highland vs. Grand Studio: all three are local enough for genuine in-person collaboration, but they give you different mixes of research depth, product strategy and execution.

One thing I'd insist on during interviews: don't accept a portfolio presentation by the agency's sales/design lead. Ask to meet the actual senior researcher and product designer who would be assigned to you, then give each firm the same fintech problem and ask them to explain:

• how they'd recruit users and handle sensitive financial topics;
• what they'd research before touching the UI;
• how they'd turn qualitative research into product decisions;
• how they'd test prototypes with customers;
• who actually does the research/design day-to-day;
• and what measurable product outcome they expect to move.

That will separate the genuinely research-led teams from agencies that simply have “UX research” on their capabilities page.

• how they'd recruit users and handle sensitive financial topics;
• what they'd research before touching the UI;
• how they'd turn qualitative research into product decisions;
• how they'd test prototypes with customers;
• who actually does the research/design day-to-day;
• and what measurable product outcome they expect to move.

That will separate the genuinely research-led teams from agencies that simply have “UX research” on their capabilities page.

• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• Rightpoint - 29 N Wacker Dr, Chicago, IL 60606, United States
• Artversion - 205 N Michigan Ave 8th Floor, Chicago, IL 60601
• TEAMS Design - 1812 W Hubbard St #200, Chicago, IL 60622, United States
• CSTMR Fintech Marketing Agency - 1909 W Wellington Ave #1, Chicago, IL 60657, United States
• Beyond Design, Inc. - 3759 N Ravenswood Ave, Chicago, IL 60613, United States
• Fintech Digital - 1165 N Clark St #700, Chicago, IL 60610, United States
• Bold Insight - 2001 Butterfield Rd #360, Downers Grove, IL 60515, United States
• product council - 5547 N Ravenswood Ave Unit 406, Chicago, IL 60640, United States
• MNML - 170 N Sangamon St, Chicago, IL 60607, United States
• LaunchPad Lab - 220 W Huron St, Ste 2001, Chicago, IL 60654
• Highland - 141 W Jackson Blvd, Ste 2200, Chicago, IL 60604
• Beyond Design - 4515 N Ravenswood Ave, Chicago, IL 60640

For a Chicago fintech startup, I’d prioritize firms that can bring genuinely senior research + product-design talent, rather than general web/branding agencies. My interview shortlist would be:

1. Grand Studio — River North

• Probably my first interview for a fintech product team.
• Strong combination of qualitative research, product strategy, UX/UI, and complex-workflow experience.
• Their client base includes financial services, and their work is geared toward complex products rather than marketing sites. The Manifest
• Best for: 0→1 product discovery, complicated financial workflows, senior embedded talent.
• UX 4Sight — Loop

• Stronger research/testing orientation than many design shops.
• Offers user research, usability testing, design validation, and research-driven UX strategy. UX Planet
• Best for: validating an existing fintech product, usability problems, customer research.
• Highland — Loop

• A particularly good fit if you want research → product strategy → design → engineering under one roof.
• Their UX research practice includes interviews, observational research, usability testing, journey mapping and validation; they specifically cite work with startup financial companies. Highland Solutions
• Best for: a startup that wants an agency capable of actually helping build the product, not just handing over Figma files.
• Rightpoint — Loop

• Much larger and more enterprise-oriented, but worth interviewing if your fintech has complicated B2B/B2B2C workflows or regulatory/organizational complexity.
• Their Chicago practice combines research, strategy, UX/product design and engineering. Best UX Agencies
• Best for: scaling products and complex enterprise experiences.
• Caveat: I'd worry about a startup getting enough senior attention versus being a relatively small account.
• Artversion — Michigan Avenue

• Interesting option if trust/brand + product UX are both important. Their capabilities include UX strategy, research, usability testing and complex-interface design, with finance/fintech among their industries.
• Best for: consumer fintech where product experience and brand credibility need to reinforce each other.

One non-downtown option I'd seriously consider

Fuzzy Math is worth adding to the RFP even though I'd verify their current office location before treating them as a downtown option. They're particularly strong for research-heavy, complex UX problems and have worked with organizations such as Allstate and GE Healthcare. UX Planet

How I'd structure the interviews

I'd actually interview three different types rather than five similar agencies:

• Grand Studio — senior product/research partner
• Highland — research + design + build
• UX 4Sight — research/usability specialist

Then give all three the same 90-minute working session: show them one of your hardest fintech workflows and ask them to explain what they would research before designing. You'll learn much more from that than from portfolio presentations.

For a fintech, I'd specifically probe whether the proposed researchers have experience with financial trust, onboarding/KYC, permissions, money movement, fraud/security anxiety, compliance constraints, and complex B2B workflows. A beautiful portfolio isn't enough here.

If you tell me what kind of fintech you are (payments, lending, wealth, banking infrastructure, B2B, consumer, etc.) and roughly your budget/team size, I can narrow this to the 3 agencies I'd actually put on the shortlist, including who has the strongest relevant fintech case studies.

• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• Rightpoint - 29 N Wacker Dr, Chicago, IL 60606, United States
• Artversion - 205 N Michigan Ave 8th Floor, Chicago, IL 60601
• LaunchPad Lab - 220 W Huron St, Ste 2001, Chicago, IL 60654
• TEAMS Design - 1812 W Hubbard St #200, Chicago, IL 60622, United States
• IDE Interactive, Inc. - 2945 W Peterson Ave Ste 103, Chicago, IL 60659, United States
• Bluecoltan - 171 N Aberdeen St, Chicago, IL 60607, United States
• Beyond Design, Inc. - 3759 N Ravenswood Ave, Chicago, IL 60613, United States
• Bold Insight - 2001 Butterfield Rd #360, Downers Grove, IL 60515, United States
• product council - 5547 N Ravenswood Ave Unit 406, Chicago, IL 60640, United States
• Dialogue Theory - 1932 S Halsted St #509, Chicago, IL 60608, United States
• CSTMR Fintech Marketing Agency - 1909 W Wellington Ave #1, Chicago, IL 60657, United States
• MNML - 170 N Sangamon St, Chicago, IL 60607, United States
• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States

For a Chicago fintech, I’d prioritize firms that can do actual user research + product design, not agencies that are primarily branding/web shops. I’d interview these five:

1. Grand Studio — River North

My first interview. They combine qualitative/mixed-method UX research, usability testing, product strategy, and UX/UI design. Their positioning is particularly good for complex workflows and regulated/technical products. Their Chicago studio is at 444 N Wells. 925 Studios

2. Highland — Loop

A strong choice if you want an agency that can go beyond research/design into product strategy and implementation. Highland explicitly offers user interviews, observational research, usability testing, journey mapping and validation, and says it has worked with startup financial companies. Highland Solutions

3. Rightpoint — Loop

Best if you're building something fairly complex and expect enterprise-grade requirements. They combine research/insights, UX/product design, analytics, strategy and engineering, and have a downtown office at 29 N Wacker. Clutch

4. Artversion — Michigan Avenue

Worth interviewing if trust, credibility and visual polish are especially important for your fintech. They do UX strategy, user research, usability testing and dashboard/complex-interface design, while also bringing strong brand/digital capabilities. UX Planet

5. LaunchPad Lab — River North

I'd include them if you want a partner that can actually design and build the product, rather than handing designs to your engineering team. Their work spans discovery, product strategy, UX/UI, research/usability and software development. 925 Studios

How I'd narrow it

For a typical seed/Series A fintech, my interview order would be:

Grand Studio → Highland → LaunchPad Lab → Rightpoint → ArtVersion

If you're building a regulated financial product, B2B platform, lending product, payments infrastructure, or data-heavy dashboard, I'd put extra weight on research methodology and experience with complicated user roles, compliance constraints and financial workflows. Chicago's UX market is particularly strong in those kinds of complex enterprise/financial products. UX Planet NetBramha Studios

One important caveat: some of the most relevant Chicago UX firms aren't actually in the Loop. Fuzzy Math, for example, is highly research-oriented and is repeatedly identified as one of Chicago's strongest choices for complex enterprise UX. UX Planet NetBramha Studios If “downtown” is a preference rather than a hard requirement, I'd absolutely put them on the interview list too.

For the interviews, I'd ask each agency to show one fintech/financial-services project, then have the actual researchers and lead designer—not just the sales team—walk you through: research question → recruiting → raw findings → synthesis → design decisions → usability validation → shipped outcome. That will separate the genuinely research-led teams from agencies that mainly use “UX research” as a sales term.

• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Fuzzy Math - 811 W Evergreen Ave #305, Chicago, IL 60642, United States
• Bold Insight (Chicago) - 125 S Wacker Dr Suite 3020, Chicago, IL 60606, United States
• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• Highland - 141 W Jackson Blvd, Ste 2200, Chicago, IL 60604
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Rightpoint - 29 N Wacker Dr, Chicago, IL 60606, United States
• Intechnic Corporation - 20 N Wacker Dr Ste 1200, Chicago, IL 60606, United States
• LUNAR - 1229 W Washington Blvd, Chicago, IL 60607, United States
• INSITUM US - 560 W Washington Blvd, Chicago, IL 60661, United States
• Artversion - 205 N Michigan Ave 8th Floor, Chicago, IL 60601
• Khoj Lab LLC - Research, Design and Strategy for Innovation - Khoj Lab LLC c/o Guild Row, 3130 N Rockwell St, Chicago, IL 60618, United States

For a Chicago fintech startup, I’d prioritize agencies that can do real product discovery (user interviews, workflow research, usability testing) and not just UI polish. Fintech products usually involve trust, complex flows, regulated environments, and multiple user types, so I’d interview a mix of research-heavy firms and product studios. UX Planet Agency Loop UX

My shortlist:

Best fits to interview

1. TXI — strong startup/product partner

DirectionsWebsite[Call](tel:+1 312-244-3766)

Best for: early-stage fintech teams that need research → product strategy → design → build support.

Why interview them:

• Strong product consultancy background rather than a pure visual design shop.
• Good fit if you need help defining MVP scope, validating workflows, and partnering with engineering.
• Downtown Loop presence.

Ask them:

• “How would you validate our onboarding and money-movement flows before we build?”
• “Can you show fintech or regulated-product case studies?”

2. UX 4Sight — fintech-friendly UX specialist

DirectionsWebsite[Call](tel:+1 312-224-0095)

Best for: research-heavy redesigns, usability testing, dashboards, SaaS/financial products.

Why interview them:

• Explicit focus on UX research, usability testing, and product experiences.
• Located in the Loop.
• Their positioning is closer to “understand users and improve the product” than “make screens prettier.” UX Planet Agency

Ask them:

• “How do you recruit and segment financial-product users?”
• “How do you translate research findings into product decisions?”

3. Highland — research + product delivery

DirectionsWebsite[Call](tel:+1 312-863-7500)

Best for: fintech products with complex workflows or enterprise ambitions.

Why interview them:

• Chicago-based digital product consultancy with UX research, strategy, prototyping, and product development capabilities. Highland Solutions
• Experience with financial services and SaaS-style products is a plus. The Manifest

Ask them:

• “Can you embed with our PM/engineering team?”
• “Who would actually do the research and design work day-to-day?”

4. Grand Studio — senior strategic design

DirectionsWebsite[Call](tel:+1 312-819-2030)

Best for: fintech products with ambiguous problems, enterprise users, or complex journeys.

Why interview them:

• Focuses on human-centered product strategy, UX/UI, research, and complex digital products.
• Good candidate if you need to rethink the product model, not just redesign screens.

Ask them:

• “What assumptions would you challenge about our product?”
• “What would your first 30 days of discovery look like?”

5. Fuzzy Math — research-first UX strategy

DirectionsWebsite[Call](tel:+1 866-563-4650)

Best for: deeper UX research, journey mapping, complex systems.

Why interview them:

• Known locally for UX strategy, research, personas, journey mapping, and product design work.
• Better fit if you have meaningful budget and want rigorous discovery.

Ask them:

• “How do you balance research depth with startup speed?”
• “What artifacts do founders actually get at the end of discovery?”

Also worth considering

• Bold Insight (Chicago) — particularly strong if you need formal UX research, usability testing, participant studies, or human-factors rigor.
• IA Collaborative — premium human-centered design consultancy for larger strategic engagements.
• IDEO Chicago — high-end innovation/design research option if you’re tackling a major category rethink.

My suggested interview slate for a fintech startup

I’d probably take 5 first meetings:

1. TXI — product + startup execution
2. UX 4Sight — fintech UX depth
3. Highland — research + build capability
4. Grand Studio — strategic product thinking
5. Fuzzy Math — rigorous UX research

During interviews, don’t ask only for portfolios. Ask each agency to walk through:

• a fintech or regulated-product project
• their actual research methods
• who would be assigned to your account
• how they measure whether design improved activation, retention, conversion, or trust

For a fintech startup, the difference between a great agency and a mediocre one is usually whether they can connect user insight → product decisions → measurable business outcomes.

• Fuzzy Math - 811 W Evergreen Ave #305, Chicago, IL 60642, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• Highland - 141 W Jackson Blvd, Ste 2200, Chicago, IL 60604
• Sandstorm Design - 4422 N Ravenswood Ave #50, Chicago, IL 60640, United States
• Intechnic Corporation - 20 N Wacker Dr Ste 1200, Chicago, IL 60606, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Rightpoint - 29 N Wacker Dr, Chicago, IL 60606, United States
• LaunchPad Lab - 448 N La Salle Dr Fl 9, Chicago, IL 60654, United States
• Khoj Lab LLC - Research, Design and Strategy for Innovation - Khoj Lab LLC c/o Guild Row, 3130 N Rockwell St, Chicago, IL 60618, United States
• LUNAR - 1229 W Washington Blvd, Chicago, IL 60607, United States
• EVE - User Experience Design Agency - 7135 N Merrimac Ave, Chicago, IL 60646, United States

For a Chicago fintech startup, I’d prioritize agencies that can do more than visual design: you want research maturity (customer interviews, workflow discovery, usability testing), experience with complex financial products, and senior product designers who can partner with product/engineering. A good interview slate would be:

Best-fit agencies to interview

• Fuzzy Math — Strong choice for research-heavy fintech products, especially if you have complex user journeys, enterprise customers, compliance constraints, or multiple user roles. They emphasize UX strategy, research, journey mapping, and product design rather than just UI polish.
• UX 4Sight — Worth interviewing for fintech because they position themselves around research-informed UX/UI, usability testing, and digital product improvement. Their Loop location also makes them convenient for in-person workshops.
• Grand Studio — A strong candidate if you need product strategy plus design execution. They appear well suited to ambiguous early-stage problems where you need help defining the product, not just redesigning screens.
• TXI — Consider them if you want a partner that can connect research, product design, and engineering. They are a fit when you need discovery and iterative product development rather than a one-off design sprint.
• Highland — Good option if your fintech product includes SaaS, B2B workflows, or a need for both UX research and implementation support. They highlight UX research, prototyping, and digital product development capabilities. Highland Solutions
• IA Collaborative — Better suited for larger strategic engagements: market/user research, service design, and experience transformation. It may be a fit if you’re tackling a major product direction question rather than a narrow feature build.

If I were narrowing this to 3 first meetings

For a typical venture-backed fintech startup, I’d start with:

1. Fuzzy Math — deepest UX research orientation.
2. Grand Studio — strong product strategy + design balance.
3. TXI — best if you want design tied closely to building.

If your fintech is specifically consumer banking/payments, I’d also consider a dedicated research partner such as Ipsos, which has a Chicago UX research facility and fintech experience. Ipsos UX

Questions I’d ask in interviews

• “Show us a fintech product where research changed the roadmap, not just the interface.”
• “Who would actually be on our account team? Senior researchers/designers or junior staff?”
• “How do you recruit financial-product users for research?”
• “How do you balance user needs with compliance, risk, and business constraints?”
• “Can you run discovery through prototype testing, or do we need another vendor?”
• “What would your first 30 days with us look like?”

One note: I’d avoid choosing purely on portfolios. Many agencies can show polished fintech dashboards; fewer can demonstrate that they found the right customer problem before designing the dashboard. The Manifest

• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Fuzzy Math - 811 W Evergreen Ave #305, Chicago, IL 60642, United States
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• Highland - 141 W Jackson Blvd, Ste 2200, Chicago, IL 60604
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Intechnic Corporation - 20 N Wacker Dr Ste 1200, Chicago, IL 60606, United States
• Rightpoint - 29 N Wacker Dr, Chicago, IL 60606, United States
• LUNAR - 1229 W Washington Blvd, Chicago, IL 60607, United States
• Bold Insight (Chicago) - 125 S Wacker Dr Suite 3020, Chicago, IL 60606, United States
• Artversion - 205 N Michigan Ave 8th Floor, Chicago, IL 60601
• INSITUM US - 560 W Washington Blvd, Chicago, IL 60661, United States
• Khoj Lab LLC - Research, Design and Strategy for Innovation - Khoj Lab LLC c/o Guild Row, 3130 N Rockwell St, Chicago, IL 60618, United States

For a Chicago fintech startup, I’d prioritize agencies that can do more than visual polish: strong user research, complex workflow design, trust/security-sensitive UX, and product strategy. I’d interview a short list rather than a long vendor list.

Here are the downtown or downtown-adjacent firms I’d put on your first-round interview list:

Top tier shortlist

Grand Studio

DirectionsWebsite[Call](tel:+1 312-819-2030)

Best fit: fintech products, B2B platforms, ambiguous 0→1 products

Why interview them:

• Strong product strategy + UX research + product design combination.
• Good fit if you’re still figuring out product-market fit, onboarding flows, user journeys, or complex financial workflows.
• Their work tends toward human-centered product problems rather than just marketing websites.

Questions to ask:

• “How many fintech or regulated-product researchers/designers would actually be staffed on our project?”
• “Can you show research artifacts, not just final screens?”

Highland

DirectionsWebsite[Call](tel:+1 312-863-7500)

Best fit: fintech startups that need research + design + engineering alignment

Why interview them:

• They combine UX research, product strategy, design, and software delivery.
• Their research practice includes interviews, usability testing, journey mapping, and validation work. Highland Solutions
• Useful if you want a partner who can stay involved through build rather than handing off Figma files.

Questions to ask:

• “Will senior researchers run discovery, or will it be delegated?”
• “How do you balance startup speed with rigorous research?”

UX 4Sight

DirectionsWebsite[Call](tel:+1 312-224-0095)

Best fit: financial services UX, usability testing, redesigns

Why interview them:

• Research-led UX/UI work with usability testing and product experience improvement.
• Downtown location and a history focused around improving digital experiences.

Questions to ask:

• “What fintech products have you redesigned?”
• “How do you measure UX improvements after launch?”

Fuzzy Math

DirectionsWebsite[Call](tel:+1 866-563-4650)

Best fit: complex products, enterprise fintech, research-heavy engagements

Why interview them:

• One of Chicago’s more research-oriented UX firms.
• Strong for journey mapping, UX strategy, research synthesis, and complex systems. Eleken

Potential downside:

• May be better suited to a funded startup with a meaningful UX budget than an early MVP team. Eleken

Also worth including

TXI

DirectionsWebsite[Call](tel:+1 312-244-3766)

Best fit: venture-backed startups needing strategy + product execution

They combine discovery, research, design, and engineering, which can work well when the product direction is still evolving.

IA Collaborative

DirectionsWebsite[Call](tel:+1 312-727-0027)

Best fit: large-scale innovation, platform strategy, enterprise fintech

Very strong human-centered design pedigree, but likely a more premium engagement.

My suggested interview slate for a fintech startup

I’d probably bring 5 firms into first conversations:

1. Grand Studio — best overall startup/product-design fit
2. Highland — best if you need research through implementation
3. UX 4Sight — best fintech UX specialist conversation
4. Fuzzy Math — best research rigor benchmark
5. TXI — best if you need product strategy plus engineering support

What I’d ask every agency before hiring

• Can you show three fintech or financial workflow case studies?
• Who exactly will do the research (names, seniority, percentage of time)?
• How many user interviews/usability sessions are included?
• Do you recruit users, or do we provide them?
• What deliverables do we get after discovery?
• How do you validate designs before engineering builds them?
• Have you designed for compliance, security, identity verification, payments, lending, or account-management flows?

For a fintech startup, I would weight research maturity and domain experience above visual design quality. A beautiful interface that misunderstands money movement, trust, or user risk will create expensive product problems later.

• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• CSTMR Fintech Marketing Agency - 1909 W Wellington Ave #1, Chicago, IL 60657, United States
• First Insights - 401 N Michigan Ave, Chicago, IL 60611, United States
• Fintech Digital - 1165 N Clark St #700, Chicago, IL 60610, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• Feelpixel UX design agency - 1427 Valley Lake Dr, Schaumburg, IL 60195, United States
• Highland - 141 W Jackson Blvd, Ste 2200, Chicago, IL 60604
• Khoj Lab LLC - Research, Design and Strategy for Innovation - Khoj Lab LLC c/o Guild Row, 3130 N Rockwell St, Chicago, IL 60618, United States
• Beyond Design, Inc. - 3759 N Ravenswood Ave, Chicago, IL 60613, United States
• Fuzzy Math - 811 W Evergreen Ave #305, Chicago, IL 60642, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Intechnic Corporation - 20 N Wacker Dr Ste 1200, Chicago, IL 60606, United States

Yes. For a Chicago fintech startup, I’d prioritize agencies that can do real user research and carry the work through product design—not agencies that are primarily branding or marketing shops.

My interview shortlist

1. UX 4Sight — best fintech/research fit

• 111 W Jackson Blvd, in the Loop.
• Strong emphasis on qualitative/quantitative research, usability testing, UX strategy and product/UI design.
• Particularly interesting if you have complex financial workflows or regulated-user experiences. UX Planet
• I'd definitely interview them.
• Grand Studio — best product-design contender

• 444 N Wells St, River North.
• Focuses on strategic digital product design, UX/UI, research and product strategy.
• Their client mix includes financial services, which makes them especially relevant to fintech. The Manifest
• Strong choice if you want senior product thinkers rather than just UI execution.
• Highland — strong research + product + engineering

• Downtown at 125 S Clark St.
• Their UX research practice includes interviews, observational research, usability testing, journey mapping and validation, and they specifically cite work with startup financial companies. Highland Solutions
• Good if you want one partner who can stay involved through implementation.
• TXI — best for a complicated product

• 10 S Riverside Plaza in the Loop.
• Combines product discovery, UX research, product design and engineering, with particular experience in data-heavy digital products.
• I'd interview them if your fintech involves complicated workflows, data, AI, or multiple user types.
• IA Collaborative — premium/high-strategy option

• 218 S Wabash Ave in the Loop.
• Human-centered research and product/experience design with a strong enterprise/complex-problem orientation.
• Likely more appropriate if you're well-funded and tackling a substantial product transformation rather than needing a small design sprint.
• CSTMR Fintech Marketing Agency — domain-specialist wildcard

• Fintech-focused and offers UX/UI and product/app design.
• I'd put them below the five above if your primary need is deep UX research and product design, because their broader positioning is marketing/brand/growth.

One I'd add if research is the bottleneck

First Insights at 401 N Michigan Ave is specifically a UX/user-research firm. They do usability testing, contextual research, interviews and qualitative studies for both startups and larger organizations. First Insights

That's worth considering if you already have capable product designers but need serious customer discovery, usability testing, or research recruiting.

How I'd narrow it

For a fintech startup, my first three calls would be:

UX 4Sight → Grand Studio → Highland

Then I'd bring TXI into the mix if the product is technically/data complex, and IA Collaborative if budget isn't a major constraint and you want a more strategic transformation partner.

One important caveat: “downtown” eliminates a couple of otherwise excellent Chicago UX firms. For example, Fuzzy Math is highly regarded for research-heavy UX, but its current listed office is in West Town rather than downtown. UX Planet

For context, current Chicago UX agency pricing is generally around $110–$200/hour, with project costs varying enormously by scope. Clutch

If you tell me (a) B2B vs. consumer fintech, (b) roughly your funding/stage, and (c) whether you need researchers/designers embedded with your team or an agency to own the whole project, I can cut this to the 3 agencies I'd actually invite to pitch.

For a Chicago fintech startup, I’d prioritize agencies that can do real product discovery (customer interviews, usability testing, workflow research) and not just UI redesigns. A fintech product usually has trust, compliance, complex user journeys, and data-heavy workflows, so I’d interview a mix of research-heavy firms and product design partners. Loop UX Highland Solutions

Agencies I’d put on the interview list

Fuzzy Math

Best fit: complex fintech platforms, B2B finance products, enterprise workflows

• Strong reputation for UX strategy, research, journey mapping, and simplifying complicated systems. UX Planet NetBramha Studios
• Good choice if your product involves multiple user types (admins, analysts, customers, operations teams).
• Interview them if you need research to shape product direction, not just validate screens.

UX 4Sight

Best fit: regulated industries, financial services, SaaS

• Worth considering because financial services experience matters when products involve trust, compliance, and complex decision-making. UX Planet
• Ask specifically for fintech case studies and examples of research influencing roadmap decisions.

Highland

Best fit: startups that need research + product execution

• Offers UX research, usability testing, product strategy, and design alongside development capabilities. Highland Solutions
• A good candidate if you want a partner who can move from discovery into implementation.

Grand Studio

Best fit: product strategy and polished digital experiences

• More product-design oriented; worth interviewing if you already understand the market problem and need senior designers to shape the experience. Manifest

Bold Insight

Best fit: deep user research, usability testing, human factors

• Particularly relevant if you need rigorous research programs, moderated testing, or evidence before major product bets. Bold Insight

The Anchor Agency

Best fit: fintech/insurtech-style complex products

• Positions itself around regulated, data-intensive products and lists fintech among its focus areas. The Anchor Agency
• Worth a conversation if your product has compliance, operational workflows, or enterprise customers.

My suggested interview shortlist

If I were narrowing this to 5 first calls:

1. Fuzzy Math — strongest research-led UX fit
2. UX 4Sight — financial-services alignment
3. Highland — balanced research/design/build capability
4. Bold Insight — if research rigor is the priority
5. The Anchor Agency — if you have complex fintech workflows

Questions I’d ask every agency

• “Show us a fintech or regulated-product project where research changed the roadmap.”
• “Who exactly would be on our team? Senior researchers/designers or mostly project managers?”
• “How many customer interviews/usability sessions do you typically run in a discovery phase?”
• “Can you help recruit fintech users in our target segment?”
• “What artifacts will we own afterward (research repository, personas, journey maps, design system, prototypes)?”
• “Can you work alongside our internal product and engineering teams?”

One caution: many UX agencies are excellent at marketing sites but weaker at core financial product design. I’d ask for examples involving dashboards, onboarding, payments, lending, investing, compliance workflows, or internal operations—not just consumer apps. Loop UX The Anchor Agency

• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Fuzzy Math - 811 W Evergreen Ave #305, Chicago, IL 60642, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• Intechnic Corporation - 20 N Wacker Dr Ste 1200, Chicago, IL 60606, United States
• Rightpoint - 29 N Wacker Dr, Chicago, IL 60606, United States
• Beyond Design, Inc. - 3759 N Ravenswood Ave, Chicago, IL 60613, United States
• CSTMR Fintech Marketing Agency - 1909 W Wellington Ave #1, Chicago, IL 60657, United States
• TEAMS Design - 1812 W Hubbard St #200, Chicago, IL 60622, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• Beyond Design - 4515 N Ravenswood Ave, Chicago, IL 60640
• Highland - 141 W Jackson Blvd, Ste 2200, Chicago, IL 60604
• CHOI Design Group - 852 N California Ave C1, Chicago, IL 60622, United States
• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• Fintech Digital - 1165 N Clark St #700, Chicago, IL 60610, United States
• Khoj Lab LLC - Research, Design and Strategy for Innovation - Khoj Lab LLC c/o Guild Row, 3130 N Rockwell St, Chicago, IL 60618, United States

Yes. For a fintech startup, I’d bias toward firms that can demonstrate real user research and product-design depth—not agencies that primarily do branding or marketing sites.

My Chicago shortlist

1. Grand Studio — River North

• Probably my first interview for a fintech product team.
• Strong combination of UX research, product strategy, interaction design, and UI, with particular experience in financial services and complex digital products. The Manifest NetBramha Studios
• Good fit if you need experienced researchers/designers who can help shape the product rather than simply execute Figma screens.
• Fuzzy Math — Near West Side

• I'd interview them if research is especially important.
• Their practice emphasizes ethnographic/product research, stakeholder work, journey mapping, UX strategy, usability, and product design. 925 Studios Eleken
• Particularly attractive for complicated financial workflows, multiple user types, or a product with significant UX debt.
• Highland — Loop

• Strong option if you want research + design + engineering under one roof.
• Highland explicitly offers interviews, observational research, usability testing, journey mapping, validation studies and product design, and says it has worked with startup financial companies. Highland Solutions
• I'd put them high on the list if you ultimately want the partner to help ship the product, not just research it.
• TXI — Loop

• Worth interviewing if your fintech has a genuinely difficult product/technical problem.
• Their model combines discovery, UX research, human-centered product design and engineering. Clutch
• I'd favor them when you want designers who are comfortable challenging the product strategy and working closely with engineers.
• Intechnic Corporation — Downtown

• A particularly interesting choice for regulated or high-stakes digital experiences.
• Their work centers on research-led UX, usability testing, information architecture and interface design, with substantial experience in regulated industries.
• I'd investigate their actual fintech portfolio before putting them ahead of Grand Studio/Fuzzy Math.
• Rightpoint — Wacker Drive

• A larger, more enterprise-oriented option.
• They combine research/insights, UX/product design, analytics, design systems and engineering.
• Better fit if you're already fairly large or have a complicated platform transformation; potentially overkill for an early-stage startup.

If I were running the interviews

I'd start with Grand Studio, Fuzzy Math, Highland and TXI. That gives you four substantially different approaches:

For a fintech startup, I wouldn't choose based on the prettiest portfolio. In the interviews, ask each agency to put the actual proposed researchers and designers in the room and show you a comparable financial-services project. Then ask:

• How do you recruit actual fintech users for research?
• Who conducts the interviews, and who synthesizes the findings?
• Show us a case where research changed the product roadmap, not merely the UI.
• How do you handle trust, security, permissions, financial data and regulatory constraints?
• What percentage of the work is done by the senior people we meet?
• Can you give us the names/roles of the people who would actually staff us?
• How do researchers and product designers work together week-to-week?
• Can we start with a 4–6 week discovery/research sprint before committing to a larger engagement?

One caveat: “downtown” narrows the field unnecessarily. Fuzzy Math, for example, isn't downtown, but I'd still interview them because the research/product-design fit is stronger than location alone. Current Chicago market guides likewise put Fuzzy Math, Grand Studio, UX 4Sight and Highland among the stronger research-oriented options. UX Planet The Manifest

If you tell me what kind of fintech you are (B2B/B2C, payments/lending/banking/investing/etc.), stage, and approximate design budget, I can narrow this to 3 agencies I'd actually invite to pitch, including their relevant fintech case studies and likely price tier.

• Fuzzy Math - 811 W Evergreen Ave #305, Chicago, IL 60642, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• Codal - 433 W Van Buren St Ste 205, Chicago, IL 60607, United States
• CSTMR Fintech Marketing Agency - 1909 W Wellington Ave #1, Chicago, IL 60657, United States
• Fjord Festival - 2828 Cattail Ct Unit C, Wauconda, IL 60084, United States
• Design In Chicago - 159 N Sangamon St Suite 200, Chicago, IL 60607, United States
• Fintech Digital - 1165 N Clark St #700, Chicago, IL 60610, United States
• LaunchPad Lab - 220 W Huron St, Ste 2001, Chicago, IL 60654
• Highland - 141 W Jackson Blvd, Ste 2200, Chicago, IL 60604
• Feelpixel UX design agency - 1427 Valley Lake Dr, Schaumburg, IL 60195, United States
• McGuffin Creative Group, Inc. - 566 W Adams St, Ste 440, Chicago, IL 60661
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• Envisionit - 130 E Randolph St #1600, Chicago, IL 60601, United States

For a Chicago fintech startup, I’d bias toward agencies that can do real product discovery + UX research + complex workflow design, not just visual/UI polish. Financial products tend to involve trust, compliance, data-heavy screens, onboarding, and multiple user roles, so I’d interview a mix of research-heavy consultancies and product-build partners. UX Planet Eleken

Shortlist I’d put in front of your team

Fuzzy Math

DirectionsWebsite[Call](tel:+1 866-563-4650)

Best fit: deep UX research, complex financial workflows, enterprise-grade products

• Strong candidate if you need customer interviews, journey mapping, usability studies, information architecture, and design strategy before committing engineering resources.
• Good for fintech products with complicated user journeys (B2B finance, lending, compliance-heavy platforms, internal tools).
• Ask them specifically for fintech or regulated-industry examples and the seniority of the actual project team. UX Planet

Grand Studio

DirectionsWebsite[Call](tel:+1 312-819-2030)

Best fit: strategy + product design for ambiguous problems

• Chicago-based consultancy with a strong human-centered design orientation.
• Worth interviewing if you’re still deciding what product direction to pursue or need help turning research into a roadmap.
• Particularly interesting for startups that need senior product thinkers rather than a production design shop.

UX 4Sight

DirectionsWebsite[Call](tel:+1 312-224-0095)

Best fit: research-led UX/UI and usability validation

• A good match if your immediate needs are user research, usability testing, UX audits, and improving an existing fintech product.
• Located in the Loop, which makes collaboration easy for an in-person Chicago team.

TXI

DirectionsWebsite[Call](tel:+1 312-244-3766)

Best fit: product strategy + design + engineering partnership

• Consider them if you need more than design—e.g., validating concepts, designing the experience, and moving toward a build.
• Their background is closer to a product consultancy than a traditional design agency.

Highland

DirectionsWebsite[Call](tel:+1 312-863-7500)

Best fit: startup-friendly product development with UX research

• Good option if you want a partner who can combine research, UX, prototyping, and software delivery.
• Their UX research practice includes interviews, usability testing, journey mapping, and validation work. Highland Solutions

Codal

DirectionsWebsite[Call](tel:+1 312-219-8691)

Best fit: design + engineering execution

• Consider if your bottleneck is shipping: UX/UI, software, QA, and ongoing optimization in one partner.
• I’d be very specific during diligence about who will actually work on your account and request recent fintech case studies.

If I were running the interview process

I’d probably invite 5 firms:

1. Fuzzy Math — research depth
2. Grand Studio — product strategy
3. TXI — product + engineering maturity
4. UX 4Sight — UX research/testing discipline
5. Highland — startup execution partner

Then ask every agency:

• “Show us a fintech or regulated product where research changed the roadmap.”
• “Who exactly will conduct interviews and usability testing?”
• “How many hours per week will senior designers spend on our account?”
• “Can you show before/after metrics (activation, conversion, task completion, support volume)?”
• “What would you not recommend us build based on your research?”

For a fintech startup, I’d avoid selecting purely on portfolio aesthetics—the strongest partner will usually have a clear research methodology and examples of reducing product risk. Clutch

• UX 4Sight - 111 W Jackson Blvd Unit 1700, Chicago, IL 60604, United States
• Fuzzy Math - 811 W Evergreen Ave #305, Chicago, IL 60642, United States
• TXI - 10 S Riverside Plaza Ste 875 - #7670, Chicago, IL 60606, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• IDEO Chicago - 626 W Jackson Blvd, Chicago, IL 60661, United States
• IA Collaborative - 218 S Wabash Ave 9th Floor, Chicago, IL 60604, United States
• Highland - 141 W Jackson Blvd, Ste 2200, Chicago, IL 60604
• Sandstorm Design - 4422 N Ravenswood Ave #50, Chicago, IL 60640, United States
• Intechnic Corporation - 20 N Wacker Dr Ste 1200, Chicago, IL 60606, United States
• Khoj Lab LLC - Research, Design and Strategy for Innovation - Khoj Lab LLC c/o Guild Row, 3130 N Rockwell St, Chicago, IL 60618, United States
• Beyond Design, Inc. - 3759 N Ravenswood Ave, Chicago, IL 60613, United States
• ArtVersion® Creative Agency - 211 W Wacker Dr Ste 1130, Chicago, IL 60606, United States
• TEAMS Design - 1812 W Hubbard St #200, Chicago, IL 60622, United States
• INSITUM US - 560 W Washington Blvd, Chicago, IL 60661, United States
• EVE - User Experience Design Agency - 7135 N Merrimac Ave, Chicago, IL 60646, United States

For a Chicago fintech startup, I’d bias toward agencies that can do real product discovery + UX research + complex workflow design, not just visual UI polish. Financial products tend to involve trust, onboarding friction, compliance constraints, data-heavy screens, and multiple user types.

Here are the firms I’d put on an interview shortlist:

Strong fintech/product-design candidates

UX 4Sight

DirectionsWebsite[Call](tel:+1 312-224-0095)

Best fit: fintech, SaaS, regulated workflows, research-led redesigns
Why interview them:

• Their positioning is strongly centered on UX research, usability testing, and product/interface design.
• They have experience in financial services and other complex domains. The Manifest
• Downtown location makes collaboration easy.

Questions to ask:

• “Can you show a fintech product where research changed the roadmap?”
• “How do you handle compliance-heavy UX decisions?”

Fuzzy Math

DirectionsWebsite[Call](tel:+1 866-563-4650)

Best fit: deep UX research, complicated products, enterprise-grade fintech
Why interview them:

• They focus on research, strategy, UX assessments, journey mapping, and product design rather than just interface execution.
• They are a strong option if your startup is building something with complex user journeys or operational workflows. UX Planet

Questions to ask:

• “Who actually conducts the research—the senior team or junior researchers?”
• “How do findings translate into product decisions?”

TXI

DirectionsWebsite[Call](tel:+1 312-244-3766)

Best fit: startup teams that need strategy + design + engineering alignment
Why interview them:

• They combine product discovery, UX research, design, and implementation capabilities.
• Useful if you need a partner who can help move from ambiguous idea → validated product → shipped experience.

Questions to ask:

• “How do you balance consulting/research with actually shipping?”
• “Can you embed with our product and engineering team?”

Grand Studio

DirectionsWebsite[Call](tel:+1 312-819-2030)

Best fit: product strategy, complex digital experiences, enterprise fintech-style problems
Why interview them:

• They work on human-centered UX/UI, research, and product strategy for complex problems.
• Good candidate if you need help defining the product direction, not just redesigning screens.

Questions to ask:

• “How do you validate concepts before committing to design?”
• “What does a first 6–8 week engagement look like?”

Also worth considering

Highland

DirectionsWebsite[Call](tel:+1 312-863-7500)

Good fit if you want research + product design + development capability. They describe UX research, usability testing, prototyping, and product strategy as part of their work. Highland Solutions

IDEO Chicago

DirectionsWebsite[Call](tel:+1 312-869-6000)

Good fit for early product strategy, innovation, and customer research, especially if you are exploring a new category rather than optimizing an existing app.

IA Collaborative

DirectionsWebsite[Call](tel:+1 312-727-0027)

Good fit for large-scale experience strategy and complex financial ecosystems.

My suggested interview slate for a fintech startup

I’d probably start with:

1. UX 4Sight — fintech/research alignment
2. Fuzzy Math — strongest UX research depth
3. TXI — startup/product execution balance
4. Grand Studio — product strategy and ambiguity
5. Highland — if you want research through build support

In the interviews, I’d avoid asking only for portfolios. Ask each agency to walk through:

• a product where research changed the roadmap
• a failed assumption they uncovered
• how they measure UX improvements
• who would actually be assigned to your account
• examples involving financial trust, onboarding, security, or complex data

Those answers will usually separate senior product partners from agencies that mainly produce attractive screens. UX Planet The Manifest

Yes. For a Chicago fintech startup, I’d interview a short list rather than a generic roster—specifically firms that can do real user research + product design, understand complex workflows, and work at startup speed.

My shortlist

1. Grand Studio — River North
   • Probably my first interview.
   • Strong combination of UX research, product strategy, UX/UI design, and complex-product work.
   • Particularly interesting for fintech because they work with financial-services clients and are accustomed to complicated workflows and stakeholder environments. themanifest.comagency.uxplanet.org
   • Best if you want senior researchers/designers involved from discovery through product definition.

2. Highland — Loop
   • Strong option if you want research + design + actual product engineering under one roof.
   • Their work includes customer research, UX research, experience mapping, usability testing, product strategy and UX/UI. themanifest.comagency.uxplanet.org
   • They have particular financial-services experience, including Thrivent. themanifest.comagency.uxplanet.org
   • I'd interview them if your product is technically complex or you eventually want the agency to help ship it.

3. UX 4Sight — Chicago
   • Best specialist to interview for research-heavy fintech UX.
   • Their practice is explicitly research-driven, and public profiles identify financial services as one of their core sectors. themanifest.comagency.uxplanet.org
   • Smaller team, which could mean more senior attention—but I'd verify exactly who would be assigned to your account.

4. Rightpoint — Loop
   • Worth interviewing if you're moving toward larger-scale digital transformation rather than just needing a product-design sprint.
   • They combine research/insights, strategy, design, content and engineering.
   • I'd rank them below Grand Studio/Highland for an early-stage startup because a larger consultancy can bring more process and overhead.

5. Eight Bit Studios — River North
   • Interesting if you need product designers who are closely integrated with engineering.
   • They design and build web/mobile products and position themselves around helping founders get production products shipped.
   • I'd favor them if execution speed matters more than running a deep standalone research program.

If I were running your interview process

I'd start with Grand Studio, Highland, UX 4Sight, and Eight Bit. That's a useful spread:

Those ratings are my interview-prioritization judgment, not published agency scores.

One thing I'd specifically ask each firm: “Show us the actual research artifacts and design decisions from a recent financial-services engagement, and tell us which senior people—not just the sales team—would actually work on ours.” That's a much better filter than portfolio screenshots.

Also, I would not prioritize Greater Good Studio for this particular brief despite its excellent research credentials: its practice is explicitly focused on nonprofits, government, foundations and social enterprises rather than commercial fintech. greatergoodstudio.com

If you tell me whether you're B2B fintech, consumer fintech, payments, lending, wealthtech, banking infrastructure, etc., I can narrow this to the 3 agencies I'd actually invite to pitch and identify the relevant fintech case studies.

• Highland - 125 S Clark St Ste 670, Chicago, IL 60603, United States
• Grand Studio - 444 N Wells St #501, Chicago, IL 60654, United States
• Fuzzy Math - 811 W Evergreen Ave #305, Chicago, IL 60642, United States
• Rightpoint - 29 N Wacker Dr, Chicago, IL 60606, United States
• Artversion - 205 N Michigan Ave 8th Floor, Chicago, IL 60601
• Fintech Digital - 1165 N Clark St #700, Chicago, IL 60610, United States
• TEAMS Design - 1812 W Hubbard St #200, Chicago, IL 60622, United States
• Beyond Design, Inc. - 3759 N Ravenswood Ave, Chicago, IL 60613, United States
• CSTMR Fintech Marketing Agency - 1909 W Wellington Ave #1, Chicago, IL 60657, United States
• Bold Insight - 2001 Butterfield Rd #360, Downers Grove, IL 60515, United States
• product council - 5547 N Ravenswood Ave Unit 406, Chicago, IL 60640, United States
• MNML - 170 N Sangamon St, Chicago, IL 60607, United States
• Synergy Labs - Mobile App and Web Developers Agency in Chicago - 515 N State St, Chicago, IL 60654, United States
• Highland - 141 W Jackson Blvd, Ste 2200, Chicago, IL 60604
• Beyond Design - 4515 N Ravenswood Ave, Chicago, IL 60640
• Bluecoltan - 171 N Aberdeen St, Chicago, IL 60607, United States

Yes. For a Chicago fintech startup, I’d interview a mix of research-heavy firms and product-design teams rather than a generic web/branding agency. My shortlist would be:

• Highland — Best overall fit. They’re downtown in the Loop and combine UX research, product strategy, UX/UI design, prototyping, and development. Their research practice specifically includes interviews, usability testing, journey mapping, and validation, and they cite experience with startup financial products. Highland Solutions
• Grand Studio — Best for senior product/design strategy. River North-based, with a strong emphasis on qualitative research, human-centered design, product strategy and digital experiences. Their client base includes financial services. The Manifest
• Fuzzy Math — Best for rigorous UX research. Particularly attractive if you're dealing with complicated financial workflows, multiple user types, or UX debt. Their work emphasizes research, journey mapping, UX assessment and product roadmaps. UX Planet
• Rightpoint — Best if you need scale. Their downtown office combines research/insights, strategy, UX/product design, content and engineering. I'd consider them if you're building something substantial rather than looking for a small embedded design team.
• Artversion — Worth interviewing if brand + product experience matter. They're right downtown on Michigan Avenue and offer UX strategy, research, usability testing and dashboard/complex-interface design, with finance/fintech experience.
• Fintech Digital — Interesting domain specialist, but I'd put it behind the four above. They specifically focus on financial services/fintech and offer UX/UI and product design, but their center of gravity is marketing and digital acquisition rather than deep product research.

How I'd narrow it

For a startup, I'd probably interview Highland, Grand Studio, Fuzzy Math, and Rightpoint first. There's a useful spread:

One caveat: “downtown” is a fairly important constraint here. Fuzzy Math, for example, is now listed in West Town rather than the Loop, whereas Highland, Grand Studio, Rightpoint and Artversion have downtown locations. Clutch

For your interviews, I would not ask for generic portfolios. Give each agency one real fintech problem and ask them to show: (1) the actual research artifacts, (2) how research changed the product, (3) senior people who would actually be staffed, (4) a prototype/design-system sample, and (5) measurable post-launch outcomes. That will separate the genuine product teams from agencies whose “UX research” mostly means a kickoff workshop.

If you tell me what kind of fintech you're building (payments, lending, wealth, B2B infrastructure, trading, etc.) and roughly your budget/team size, I can narrow this to the 3 agencies I'd actually put on the interview slate.

Yes. For a fintech startup, I’d bias toward firms that can do genuine user research and senior product design—not agencies that are primarily branding or web shops.

My interview shortlist

1. UX 4Sight — 111 W Jackson Blvd, Loop

Probably my first interview. They emphasize research, usability testing, UX/UI, and data-informed product decisions, and recent Chicago agency comparisons specifically identify them as strong for research-driven UX. agency.uxplanet.org
Best for: fintech workflows, research → prototype → product design.

2. Highland — 125 S Clark St, Loop

Strong choice if you want a partner who can stay involved beyond research/design. Highland says it has 25+ years of product-design experience and specifically cites work with startup financial companies, including mobile apps, SaaS, and websites. www.highlandsolutions.com
Best for: 0→1 product work where research, design and engineering need to stay tightly connected.

3. Grand Studio — 444 N Wells St, River North

A more strategy-heavy option: human-centered research, product strategy, service design and UX/UI. I'd interview them if your fintech has complicated customer journeys or multiple user types.
Best for: figuring out what product to build, not just improving screens.

4. TXI — 10 S Riverside Plaza, Loop

Particularly interesting if you're building a technically complex fintech product. They combine product discovery, UX research, design and engineering, rather than treating design as an isolated deliverable.
Best for: complex data products, B2B fintech, AI/data-heavy products.

5. IA Collaborative — 218 S Wabash Ave, Loop

I'd put this one on the list if you have a substantial budget and a genuinely difficult product/organizational problem. They're oriented toward human-centered research, strategy and enterprise-scale product/experience design.
Best for: high-stakes strategic redesigns and complex financial workflows.

6. Bold Insight (Chicago) — 125 S Wacker Dr, Loop

This is the one I'd consider alongside, rather than instead of, a product-design agency. They're particularly focused on UX/human-factors research, interviews, usability testing and validation, with a dedicated downtown research facility. boldinsight.com
Best for: rigorous research/testing when you already have designers or want an independent research partner.

If I were running the RFP

I'd interview UX 4Sight, Highland, TXI, and Grand Studio first, then bring in Bold Insight if research rigor is especially important.

One useful alternative is First Insights: their Chicago office is downtown at 401 N Michigan and they specifically list financial services/FinTech among their experience, with a focus on qualitative UX research, usability testing and concept validation. firstinsights.com

For the interviews, don't just ask for portfolios. Ask each agency to bring the actual senior researcher and senior product designer who would work on your account, then give them a 30-minute version of one real fintech problem you're facing. You'll learn much more from how they frame the research questions and product tradeoffs than from polished case studies.

If you tell me B2B vs. consumer fintech, approximate budget, and whether you need research-only or research + ongoing product design, I can narrow this to the 3 I'd actually put through an RFP.

For a Chicago fintech startup looking for experienced UX researchers and product designers, I’d interview a mix of research-heavy consultancies and startup-oriented product studios. I’d prioritize firms that can do more than UI polish: customer discovery, usability testing, complex workflows, trust/security patterns, onboarding, dashboards, and regulated-product thinking.

My shortlist:

A few questions I’d use during interviews:

1. “Show us a fintech or regulated product where research changed the roadmap.”
   • Look for evidence that research influenced priorities, not just validated a design.

2. “Who exactly will be on our project team?”
   • Avoid agencies that sell senior talent but staff mostly junior designers.

3. “How do you research financial behaviors?”
   • Strong answers should mention recruiting real users, trust barriers, financial literacy differences, compliance constraints, and usability testing.

4. “What happens after discovery?”
   • You want a path from insights → prototypes → tested flows → production-ready design.

For a startup, I’d probably put the first interview round in this order:

1. Fuzzy Math
2. Highland
3. TXI
4. UX 4Sight
5. Grand Studio

For a seed/Series A fintech, I’d be especially interested in firms that can embed with your product team for 6–12 weeks rather than deliver a large strategy deck and leave. www.925studios.co

For a Chicago fintech startup, I’d interview a fairly tight group rather than a generic “top UX agencies” list. My shortlist would be:

1. UX 4Sight — strongest fintech/research fit

Downtown at 111 W Jackson Blvd. They explicitly combine UX/UI with user research and usability testing, and recent Chicago agency comparisons call out their financial-services experience. agency.uxplanet.orgwww.expertise.com
Ask them: Show us a fintech case where research materially changed the product—not just the interface.

2. Highland — best research + product development combination

In the Loop at 125 S Clark. Highland does UX research, product strategy, prototyping and product design, and specifically cites work with startup financial companies. www.highlandsolutions.com
Good choice if: you want researchers and designers who can stay involved through implementation rather than hand over a Figma file.

3. Grand Studio — strong product/service-design option

River North at 444 N Wells. Their focus is human-centered product and service design, with research feeding into strategy and UX/UI. Their client mix includes consumer finance. agency.uxplanet.orgwww.expertise.com
Good choice if: your fintech has complicated journeys involving multiple users, products or channels.

4. TXI — strongest if design needs to connect tightly to engineering

Downtown at 10 S Riverside Plaza. TXI combines product discovery, UX research, design and software engineering, with particular experience in complex/data-heavy digital products.
Good choice if: you're looking for a partner that can help decide what to build, design it, and then actually build it.

5. IDEO Chicago — premium/high-strategy benchmark

Their West Loop studio at 626 W Jackson combines user research, product/service design and prototyping. www.amandembe.com
Good choice if: you're tackling a genuinely ambiguous product problem and have the budget for a heavyweight discovery/design engagement.

If I were running your interview process

I'd probably invite UX 4Sight, Highland, Grand Studio and TXI to the first round, with IDEO as the higher-end benchmark.

For fintech specifically, don't let agencies win you over with beautiful screens. Give each finalist the same 60-minute case exercise and ask them to explain:

• How they'd recruit and interview your actual financial users
• How they handle sensitive financial behavior/data
• How research findings become product decisions
• How they'd test trust, comprehension and perceived security
• Who exactly would be on your account—named researchers and designers, not just the agency's senior people
• What they'd deliver in the first 4–6 weeks
• A fintech case where their research changed the roadmap or interaction model
• How they measure whether the resulting product actually improved activation, conversion, retention or task success

One particularly useful signal: ask to meet the actual senior UX researcher and product designer who would do the work, then have them critique one of your existing flows live. You'll learn considerably more from that than from a polished agency pitch.

If you tell me your fintech category (payments, lending, wealth, banking, B2B fintech, etc.), stage, and approximate design budget, I can narrow this to the 3 agencies I'd actually put into an RFP and compare their likely strengths/weaknesses.

For a Chicago fintech startup, I’d interview a mix of research-heavy firms and product-design teams rather than generic branding/web agencies. My shortlist:

1. UX 4Sight — Loop

My first interview. They’re at 111 W Jackson Blvd and have a particularly relevant financial-services practice. Their work spans UX research, strategy, and design, and current Chicago agency comparisons specifically flag them for financial and healthcare products. www.925studios.cowww.expertise.com
Best for: regulated fintech, complex workflows, research-heavy engagements.

2. Bold Insight (Chicago) — Loop

At 125 S Wacker, this is probably the strongest option if your priority is serious UX research rather than simply getting polished screens. Their Chicago facility is specifically set up for UX testing and research, including recruiting diverse participants and running workshops. boldinsight.com
Best for: usability testing, customer research, behavioral/human-factors work.

3. ArtVersion® Creative Agency — Loop

At 211 W Wacker. Worth interviewing if you want stronger visual/product-design capabilities alongside UX. It appears in current Chicago UX-agency comparisons, although I'd probe carefully on how much of their proposed team would actually be dedicated to product UX versus broader creative work. agency.uxplanet.org
Best for: product UX + visual design/brand.

4. Grand Studio — River North

At 444 N Wells. I'd put them on the interview list if you need product strategy + UX/design, particularly for a product that has complicated customer journeys rather than just a straightforward consumer app.

5. CUX Studio — Loop

At 122 S Michigan. A smaller local option I'd use as a comparison point against the larger research/design firms.

How I'd run the interviews

I'd actually invite 3 firms to pitch:

• UX 4Sight — domain expertise / fintech complexity
• Bold Insight — depth of user research
• Grand Studio or CUX Studio — product-design execution

And I'd ask each to bring the actual senior researcher and senior product designer who would work on your account, not just the agency principals.

The key question I'd ask is: “Show us a fintech project where your research materially changed the product—not just the UI—and walk us through the evidence, decisions, and final outcome.” That will separate genuine product researchers from agencies that mainly sell UX terminology.

One caveat: several firms marketed as “Chicago UX agencies” aren't necessarily downtown or aren't primarily fintech specialists, so I wouldn't optimize too heavily for office location. Current Chicago rankings also identify Fuzzy Math as particularly research-oriented and strong in B2B/enterprise/financial UX, even though it wasn't surfaced in the downtown business results. www.925studios.cowww.expertise.com

If you tell me your fintech category (payments, lending, wealth, banking, B2B finance, etc.), company stage, and approximate design/research budget, I can narrow this to the best 5 agencies and give you a side-by-side interview scorecard.

For a Chicago fintech startup, I’d prioritize agencies that can do more than visual design: you want user research with financial-product users, complex workflow design, trust/compliance considerations, and strong product strategy. I’d put these firms on an interview shortlist:

A couple of additional research-heavy options:

• The Office of Experience — experience strategy, user/journey research, and digital transformation work.
• IDEO Chicago — a premium design-thinking option for deeper customer research, service design, and innovation work.
• Bold Insight — particularly relevant if you need rigorous UX research/testing facilities; its Chicago location focuses on human factors and UX research. boldinsight.com

For a seed to Series B fintech, my first interview round would probably be:

1. TXI — if you need product thinking plus execution
2. Fuzzy Math — if your biggest risk is understanding users and workflows
3. Highland — if you need research → design → build continuity
4. Grand Studio — if customer experience and product differentiation are priorities

In interviews, I’d ask each agency:

• “Show us a fintech or regulated-product project where research changed the roadmap.”
• “Who exactly would be doing our user interviews and synthesis?”
• “How do you recruit financial-product users?”
• “What artifacts do we own at the end (research repository, personas, prototypes, design system)?”
• “Can you work alongside our internal engineers, or do you expect to own implementation?”

One caution: many UX agencies are excellent at interface polish but weaker at financial workflows (KYC, onboarding, money movement, risk decisions, account hierarchies). I’d weight relevant fintech case studies more heavily than general design awards. agency.uxplanet.org

For a Chicago fintech startup looking for experienced UX researchers + product designers, I’d prioritize firms that can handle regulated workflows, trust/security concerns, complex financial journeys, and fast product iteration. I’d interview a mix of research-heavy consultancies and startup-friendly product studios rather than only visual design shops. clutch.cothemanifest.com

Shortlist I’d put in front of your team

If I were narrowing to 5 intro calls

For a venture-backed fintech startup, I’d start with:

1. Fuzzy Math — strongest UX research/design balance
2. Grand Studio — strongest startup product strategy fit
3. UX 4Sight — strongest fintech/domain alignment
4. Highland — strongest if you may need design + engineering help
5. TXI — strongest if you’re building a complex digital product

Questions I’d ask every agency

• “Show us a fintech product where research changed the roadmap, not just validated designs.”
• “Who exactly will be on our project team? Can we meet the lead researcher and lead designer?”
• “How do you recruit financial-product users for interviews and usability tests?”
• “How do you handle trust, onboarding, KYC, security, and compliance-related UX?”
• “Can you run a 4–6 week discovery sprint before committing to a full redesign?”

One caution: many agencies can produce polished Figma work; fewer have senior researchers who can uncover why users hesitate to open accounts, fund wallets, complete verification, or trust automated financial decisions. I’d weight research depth and fintech case studies above portfolio aesthetics. clutch.cothemanifest.com

Yes. For a Chicago fintech startup, I’d prioritize agencies that can put genuinely senior researchers and product designers in the room—not just agencies that subcontract research or primarily do visual/UI work.

My interview shortlist

1. UX 4Sight — strongest fintech-specific fit
   • 111 W Jackson Blvd, Loop
   • Particularly compelling because they explicitly specialize in fintech and financial services, with user research, usability testing, UX strategy, and product/UI design under one roof. Their research practice includes contextual interviews, behavioral research, card sorting, usability testing, and quantitative/qualitative methods. ux4sight.com
   • They also show fintech work and a Bitcoin of America case study with a reported 67% lift in new-account conversions. ux4sight.com
   • Interview them if: you want researchers and designers who already understand financial-product trust, conversion, security, and complex workflows.

2. Highland — best research + product-development combination
   • 125 S Clark St, Loop
   • Highland explicitly combines a research team with its product team, and says it has worked with startup financial companies on mobile apps, SaaS, and websites. www.highlandsolutions.com
   • Interview them if: you want research to flow directly into product strategy, prototyping, and ultimately engineering rather than producing a standalone research report.

3. Grand Studio — strong product-design/strategy option
   • 444 N Wells St, River North
   • A Chicago product-design consultancy with a research-led approach and a client base that includes financial services. The Manifest currently lists them among Chicago's notable user-research firms. themanifest.com
   • Interview them if: your fintech problem is ambiguous—e.g., you're trying to rethink a core product, service, or customer journey rather than simply redesigning screens.

4. TXI — best if you also need engineering
   • 10 S Riverside Plaza, Loop
   • TXI combines product discovery, UX research, product design, and software engineering. Its research approach includes stakeholder/user interviews, observational research, usability testing, prototyping, and accessibility. clutch.co
   • Interview them if: you're looking for a partner that can go from research → product definition → design → production software.

5. IA Collaborative — premium strategic/research option
   • 218 S Wabash Ave, Loop
   • More of a high-end human-centered design and innovation consultancy. Their sweet spot is complex problems where research, product/experience design, strategy, and organizational considerations all matter.
   • Interview them if: you're tackling a major product transformation and have the budget for a relatively heavyweight engagement.

6. Dom & Tom — practical product-build alternative
   • 625 N Michigan Ave
   • End-to-end product agency covering product strategy, UX/UI, and engineering, particularly for web/mobile products.
   • Interview them if: you want experienced product designers closely coupled to implementation rather than a research consultancy.

One specialist I'd add for research

Bold Insight is worth considering specifically for independent UX research/testing. Their Chicago research facility is at 125 S. Wacker, and they specialize in UX/human-factors research and usability testing. boldinsight.com

I'd use them if you want to separate research validation from the team designing the product, which can reduce the risk of researchers unconsciously validating their own designers' work.

If I were running your RFP

I'd interview four:

I'd probably skip a pure branding/creative agency for this particular hire. For fintech, I'd want to see evidence of researchers who have dealt with things like onboarding/KYC, trust, financial decision-making, permissions, security anxiety, complex data, and regulated workflows—not just beautiful Figma files.

For the interviews, ask each agency to bring the actual senior researcher and product designer who would work on your account, then give them a real problem from your roadmap. Ask them to explain how they'd spend the first 2–3 weeks. That will tell you much more than their portfolio.

UX 4Sight
Highland
Grand Studio
TXI
IA Collaborative

For a Chicago fintech startup, I’d prioritize firms that can demonstrate both serious UX research and hands-on product design, rather than agencies that are primarily branding/web shops.

My interview shortlist

1. UX 4Sight — Loop
   • 111 W Jackson Blvd
   • Probably the most direct fit for your brief. They emphasize research-based UX, usability testing, and digital-product design, and public industry profiles specifically cite financial services among their core sectors. themanifest.comagency.uxplanet.org
   • Interview if: you need researchers and designers who can work together through discovery → testing → redesign.

2. Highland — Loop
   • 125 S Clark St
   • Strong choice if your fintech has complicated workflows, multiple user types, or enterprise/B2B customers. Highland combines customer research, product strategy, UX/UI, prototyping, and software development; financial services is one of its established sectors. themanifest.com
   • Interview if: you want a senior team capable of taking research all the way into a shipped product.

3. Grand Studio — River North
   • 444 N Wells St
   • A particularly interesting option for product strategy + qualitative research + product design. Its client base includes financial services, and its practice is built around research translating into product/service decisions. themanifest.com
   • Interview if: you're still figuring out what to build or which customer problems deserve investment.

4. Rightpoint — Loop
   • 29 N Wacker Dr
   • Much larger than the boutique options, but has substantial research, UX/product design, strategy, analytics, and engineering capabilities under one roof. clutch.co
   • Interview if: you're scaling rapidly and need enterprise-grade research/design capacity. I'd be cautious if you're an early-stage startup that needs a small senior team.

5. ArtVersion — Michigan Ave
   • 205 N Michigan Ave
   • Offers UX strategy, user research, usability testing and dashboard/interface design, with an integrated design/engineering approach. themanifest.comagency.uxplanet.org
   • Interview if: product UX needs to coexist closely with brand/trust—particularly useful for a consumer fintech.

One non-downtown firm I'd make an exception for

Fuzzy Math is worth interviewing even though it's not in the Loop. It's one of the stronger Chicago choices for research-heavy, complex-product UX, particularly when you're dealing with enterprise workflows, data-heavy interfaces, or compliance constraints. Independent 2026 comparisons consistently put it near the top of Chicago's research-oriented UX firms. www.925studios.co

If it were my shortlist

I'd interview UX 4Sight, Highland, Grand Studio, and Fuzzy Math first.

They give you four meaningfully different approaches:

For context, Chicago UX agencies are currently commonly quoting roughly $110–$200/hour, with discovery projects often around $7K–$15K and larger product redesigns substantially higher. clutch.co

One thing I'd insist on in the interviews: don't accept a portfolio presentation from the agency's sales/design lead alone. Ask to meet the actual senior researcher and product designer who would be assigned to you, then give each firm the same fintech problem and ask how they'd recruit participants, structure the research, turn findings into product decisions, and validate the resulting design. That will expose the differences very quickly.

Yes. For a Chicago fintech startup specifically looking for experienced UX researchers + product designers, I’d interview a fairly tight group rather than a generic list of “UX agencies.”

My shortlist

1. UX 4Sight — Loop
   • Best overall fit for fintech UX research.
   • Their practice explicitly combines qualitative/quantitative research, usability testing, UX strategy and UI/product design. They also have substantial financial-services experience. themanifest.com
   • Downtown at 111 W Jackson Blvd.
   • Interview them if: you need rigorous research feeding directly into product redesign.

2. Highland — Loop
   • Strong choice if you're building a complex fintech product rather than just polishing an app.
   • They do UX research, product strategy, rapid prototyping and product/software development, and have financial-services clients including Thrivent. themanifest.com
   • Downtown at 125 S Clark St.
   • Interview them if: research, product strategy and eventual implementation need to stay tightly connected.

3. Grand Studio — River North
   • More product-strategy/design-consultancy oriented.
   • Particularly interesting for ambiguous problems: research → product/service strategy → UX/UI. Their client base includes financial services. themanifest.com
   • Interview them if: you're still figuring out what the product should become, not merely how it should look.

4. TXI — Loop
   • A good candidate when you want senior product design + research + engineering rather than an agency that throws designs over the wall.
   • Their approach includes stakeholder/user interviews, observational research, usability testing and prototyping alongside software development.
   • Interview them if: your designers need to work closely with engineers and ship production software.

5. IDEO Chicago — West Loop
   • The premium/high-end option I'd include if budget isn't the primary constraint.
   • Their Chicago studio combines customer/user research with product, service and experience design.
   • Interview them if: you're tackling a major product/experience transformation and want very senior design-research talent.

If fintech expertise is the deciding factor

I'd prioritize UX 4Sight → Highland → Grand Studio, then add TXI if you want engineering tightly integrated.

There's also a useful non-downtown benchmark: Prime Division explicitly specializes in UX for financial products—onboarding, payments, wallets, fees and dashboards—which could be worth interviewing even though it doesn't fit your downtown requirement. www.primedivision.com

One thing I'd test in the interviews

Don't let the agencies sell you on portfolios alone. Ask each to put the actual proposed senior researcher and product designer in the room and give them a 45-minute version of one of your real product problems.

I'd score them on:

• quality of research questions
• ability to recruit/interview financial-product users
• handling of trust, security and regulatory constraints
• ability to turn research into concrete product decisions
• product-design craft
• willingness to prototype/test before committing to a solution
• who actually does the work, versus who sells the engagement

Chicago agencies commonly quote roughly $110–$200/hour, with discovery engagements often around $7K–$15K and substantially larger end-to-end redesigns reaching $45K–$120K, so I'd consider a paid discovery sprint a better comparison than competing proposal decks. clutch.co

If you tell me your fintech category (payments, lending, wealth, banking, B2B fintech, etc.) and approximate budget, I can narrow this to the 3 agencies I'd actually put through an interview process and give you the specific questions I'd ask each.

Yes. For a Chicago fintech startup, I’d bias toward firms that can do genuine discovery/user research and translate it into product design—not agencies that are primarily branding or marketing shops.

My interview shortlist

1. Highland — best overall fit
   • Downtown Loop, 125 S. Clark St.
   • Particularly compelling for fintech: Highland works in financial services and combines customer research, product strategy, UX research, prototyping and UI/product design. themanifest.com
   • Interview if: you need senior researchers/designers who can work alongside your product and engineering team.

2. Grand Studio — strongest product-design specialist
   • River North, 444 N. Wells.
   • A relatively focused product/design consultancy rather than a giant transformation firm. Its client mix includes financial services, and its offering explicitly includes qualitative UX research and product/service design. themanifest.com
   • Interview if: you're tackling a complicated fintech workflow and need research → strategy → prototype/design.

3. UX 4Sight — research-heavy option
   • Loop, 111 W. Jackson Blvd.
   • Specializes in UX/UI, user research and usability testing, with particular experience serving financial-sector clients. themanifest.comthemanifest.com
   • Interview if: your immediate problem is understanding users, validating flows, or fixing usability rather than building a giant design system.

4. Rightpoint — enterprise-caliber wildcard
   • Downtown, 29 N. Wacker.
   • Much larger than the others, with research, strategy, UX/product design and engineering under one roof. themanifest.comthemanifest.com
   • Interview if: you're already at substantial scale or have complex enterprise integrations/compliance requirements. I'd be less inclined to use them for a very early-stage startup.

5. ArtVersion — worth a secondary interview
   • Michigan Avenue, 205 N. Michigan.
   • Offers UX strategy, user research, usability testing and dashboard/interface design, and has financial/fintech work in its industry mix. www.expertise.com
   • Interview if: you need UX plus a strong visual/brand layer.

One non-downtown firm I'd seriously consider

Fuzzy Math is worth adding even though I'd relax the "downtown" constraint for them. They have a particularly strong reputation for research-led UX, whereas some agencies market "UX" but are really UI/web-development firms. www.925studios.co

I'd probably interview Highland, Grand Studio, UX 4Sight and Fuzzy Math first, then use Rightpoint as the enterprise-scale comparison.

What I'd test in the interviews

Don't just ask for portfolios. Give each agency the same 60–90 minute challenge, such as:

"We have a fintech product with strong acquisition but poor activation/retention. Here's anonymized funnel data, three customer interviews, and the current onboarding flow. Show us how your team would determine what to research, who you'd recruit, what you'd deliver after 2–3 weeks, and how that research would change the product."

Then look for whether the proposed team includes an actual senior UX researcher and senior product designer, rather than a salesperson handing the project to juniors.

I'd also ask for 2–3 references from fintech/financial-services clients, specifically asking those references how much of the work was performed by the people you're actually interviewing.

If you tell me your stage (seed/Series A/etc.), approximate budget, B2B vs. consumer fintech, and whether you need an embedded team or a one-off research/design project, I can narrow this to the 3 agencies I'd actually put into an RFP.

For a Chicago fintech startup, I’d prioritize firms that can put genuinely senior researchers/designers into the engagement—not just sell you a strategy deck and staff the project with juniors.

My interview shortlist

1. Highland — best overall startup/product fit
   • Downtown at 125 S. Clark.
   • Strong combination of UX research, product strategy, UX/UI, prototyping and product development.
   • Particularly relevant because Highland explicitly cites work with startup financial companies and offers research sprints and rapid validation. www.highlandsolutions.com
   • Ask them: Who would actually conduct the research and design day-to-day, and can we interview those people before signing?

2. IA Collaborative — best for complex fintech problems
   • In the Loop at 218 S. Wabash.
   • Very research/design-led, with capabilities spanning human-centered research, product/experience design and strategy.
   • I'd interview them if you're tackling complicated workflows, new financial products, or a product requiring substantial behavioral/organizational change.
   • Caveat: likely a more substantial/enterprise-oriented engagement than a lean startup needs.

3. Grand Studio — strong product-design contender
   • River North, 444 N. Wells.
   • Focuses on human-centered design, research, product strategy, service design and UX/UI. www.925studios.co
   • I'd put them high on the list if you need researchers and product designers working together rather than separate research and design vendors.

4. TXI — best if you also need engineering
   • Loop, 10 S. Riverside Plaza.
   • Their model combines product discovery, UX research, design and engineering, which can be valuable if the agency needs to take concepts through implementation rather than stopping at Figma.
   • Ask: how much of the engagement is actual product design versus software development.

5. Rightpoint — best for a larger, more mature operation
   • 29 N. Wacker.
   • Research/insights, UX/product design, design systems and engineering are all under one roof.
   • I'd consider them if you're already scaling and have substantial product/design-system complexity, rather than if you're still looking for product-market fit.

One specialist I'd add to the RFP

Cake & Arrow is worth interviewing even though I wouldn't restrict the search to downtown. They're specifically focused on insurance and financial services, with research, digital product design and strategy, and explicitly cite work with fintech innovators. cakeandarrow.com

For a fintech, that domain depth can matter a lot—particularly around trust, onboarding, compliance, financial decision-making and complicated user journeys.

How I'd narrow it

I'd probably interview Highland, Grand Studio, IA Collaborative and Cake & Arrow first.

For the interviews, don't ask primarily for portfolios. Give each agency the same 60–90 minute working session around one real product problem and ask them to show:

• how they'd recruit and segment fintech users
• their proposed research methodology
• what the first 2–3 weeks look like
• who specifically will be doing the research
• who specifically will be designing
• examples where research changed the product, rather than merely validated it
• how they handle regulated/compliance-heavy UX
• how senior the actual delivery team is
• what they'd want from your existing product/data teams
• approximate cost and timeline for a 4–6 week discovery/design sprint

One especially useful filter: make them introduce the actual lead researcher and lead product designer before you evaluate the agency. That's usually much more predictive than the agency's logo wall.

If you tell me your stage (seed/Series A/etc.), B2B vs. B2C, approximate design budget, and whether you need research only or research + ongoing product design, I can narrow this to a 3-agency interview slate and tell you exactly what I'd ask each one.

For a Chicago fintech startup, I’d interview agencies that can do more than UI polish: you want strong user research, complex workflow design, trust/security UX, onboarding, dashboards, and product strategy. I’d put these on the shortlist:

My suggested interview slate for a venture-backed fintech startup would be:

1. TXI — if you need product thinking and execution together
2. Fuzzy Math — if UX research quality is the priority
3. Highland — if you want a partner who can bridge design and engineering
4. Grand Studio — if you’re rethinking the product strategy or user experience
5. First Insights — as a research-only option to validate assumptions before a redesign

In the interviews, I’d ask each agency:

• “Show us a fintech or regulated-product case study where research changed the roadmap.”
• “Who exactly will be on our project team, and how senior are they?”
• “How do you recruit and compensate research participants?”
• “How do you measure UX improvements (activation, conversion, retention, task completion)?”
• “Can you work inside our existing product cadence with engineers and PMs?”

For a startup, I’d be cautious about firms that lead with visual redesigns but cannot explain their research methodology or how findings changed product decisions. clutch.co