ChatGPT answers, unedited

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