ChatGPT answers, unedited

If you mean Chicago-area agencies to interview as potential partners for a foundation website—not government grantmaking agencies—I’d put these on the shortlist:

1. LimeRed Studio, Inc. — Probably my first interview for a visually distinctive foundation site. They combine brand strategy, visual identity, UX/web development, accessibility, SEO, messaging, and integrations. Their research/stakeholder approach is particularly relevant for a foundation with multiple audiences. clutch.co

2. Dialogue Theory — Strong choice if you want strategy + storytelling + sophisticated digital experience, rather than simply a prettier WordPress site. They work with nonprofits and civic organizations and cover discovery, UX/UI, content strategy, development, and ongoing iteration. clutch.co

3. Sandstorm Design — Worth interviewing if visual design, inclusive design, accessibility, and user research are central. Their work spans brand strategy through enterprise web development.

4. Prosper Strategies — I'd add a strategy/fundraising specialist to the interview mix. Their focus is nonprofit strategy and fundraising, so they can help ensure the site's grant/donor experience isn't designed in isolation from your development strategy.

5. Promet Source — Particularly interesting if your grant applications will involve large resource libraries, complex forms, permissions, accessibility, or Drupal. They're more technology/platform-oriented than purely visual.

6. Nonprofit Megaphone — Consider them if the website also needs to drive search/discovery and Google Ad Grant traffic. Their specialty is nonprofit digital marketing and Google Ad Grant management.

7. Alford Group — A useful counterpoint to the design agencies: nonprofit fundraising and organizational strategy. I'd interview them if you want someone to pressure-test the site's fundraising/grant-seeking architecture before the designers build it.

For your particular brief

I'd actually run two kinds of interviews, rather than asking one agency to solve everything:

One important point: don't frame “grant application downloads” as merely a PDF-download feature. Chicago funders such as The Chicago Community Trust's GrantCentral resources demonstrate how grant seekers increasingly encounter responsive, web-based application workflows alongside instructions, FAQs, organizational profiles, outcomes, and supporting information. Your agency should think through that entire applicant journey.

For the RFP/interview, I'd give every agency the same challenge:

“Show us how you would design a visually compelling foundation website where a first-time grant applicant can find eligibility, deadlines, application instructions, downloadable templates, FAQs, and the actual application in under two minutes—without making the site feel like a grants portal.”

Then ask them to mock up the homepage + grant-seeker journey, rather than just showing their portfolio. That will reveal much more than another hour of agency presentations.

Yes. For a foundation that needs a highly visual site plus a genuinely usable grant-application/download experience, I’d interview agencies with different strengths rather than treating this as a generic website redesign.

My Chicago shortlist

1. Dialogue Theory — best overall fit
   • Strong combination of digital strategy, UX/UI, visual design and development.
   • Their mission-driven work makes them a particularly good candidate if the site needs to explain complex programs and guide applicants through funding processes.
   • I'd ask them to prototype the grant-seeker journey, not just the homepage.

2. LimeRed Studio, Inc. — best for visual identity + UX
   • Particularly interesting if you want the website, brand, storytelling, accessibility and content system to feel like one integrated experience.
   • Their capabilities include UX/UI, information architecture, accessibility/SEO auditing, WordPress and integrations for forms/payments/CRMs. www.project6.com

3. Sandstorm Design — best for sophisticated UX/accessibility
   • Worth interviewing if your foundation serves diverse audiences and accessibility is a serious requirement.
   • Their process emphasizes stakeholder research, design thinking, UX and inclusive design.

4. Advocate Creative — best for foundation/nonprofit storytelling
   • Their Chicago practice focuses specifically on nonprofits and foundations, including brand strategy, visual language and websites designed around actions such as funding applications.
   • I'd include them if the site needs to feel editorial, distinctive and mission-led, rather than like a conventional institutional foundation site.

5. McGuffin Creative Group, Inc. — interesting creative alternative
   • Combines branding, website/UX work and nonprofit experience.
   • Especially worth an interview because they also operate a nonprofit-focused pro-bono grant program, suggesting familiarity with organizations working under resource constraints.

6. Beth Interactive — consider if fundraising is central
   • More philanthropy/fundraising-oriented than a pure web-design shop.
   • Their digital audits and analytics work could be valuable if you want the new site to improve donor and applicant behavior, not simply look better.

One agency I'd add specifically for the grant-download problem

Project6 is worth a conversation. It explicitly works with foundations/nonprofits and lists grant and donation tools, accessibility compliance, UX/UI, usability testing, WordPress/Drupal and custom programming among its capabilities. www.project6.com

There's also a particularly relevant case study from Serenity Studios: its Miller Foundation redesign involved personas and user journeys for grant seekers, an accessible searchable grant-history database, and redesigning the grants experience around simpler language and navigation. www.serenitystudios.com That's the kind of precedent I'd use when evaluating agencies.

What I'd ask every agency to demonstrate

Don't ask, "Can you build us a beautiful website?" Ask them to respond to these five things:

• Show us a grant-seeker journey you've designed. How does someone discover eligibility → understand requirements → download forms → submit → get help?
• How would you handle PDFs? Can applicants preview them, download accessible versions, understand which version is current, and find supporting instructions?
• How would you make the site visually driven without sacrificing usability?
• Show us the CMS experience for foundation staff. Can a program officer replace a PDF, update a deadline or add an FAQ without calling the agency?
• How will you test the grant application experience with actual users?

That's important because foundation sites often fail not at the visual layer but at the information architecture around grants. For example, Impact Grants Chicago itself provides eligibility, requirements, FAQs and application questions as downloadable resources—exactly the kind of content architecture your agency should make dramatically easier to navigate. www.impactgrantschicago.org

If I were narrowing it to 3

I'd interview Dialogue Theory, LimeRed Studio, and Project6. I'd then use Advocate Creative as the fourth interview if distinctive visual storytelling/brand expression is a major priority.

For benchmarking, Chicago's nonprofit web-design market currently includes firms ranging from relatively small web shops to larger UX/development agencies; current listings show substantial variation in pricing and specialization, so I'd make the agencies respond to the same short design challenge rather than comparing proposals at face value. clutch.co

If you tell me your approximate website budget and foundation type (arts, community, education, health, etc.), I can narrow this to 3–5 agencies and give you a side-by-side interview scorecard.

Yes. If the goal is to design a visually driven foundation website that also makes grant applications and downloadable materials genuinely easy to use, I’d interview people who actually experience the grant-seeking process—not just web designers.

My Chicago shortlist

1. The Chicago Community Trust — probably the highest-priority interview. Its GrantCentral system is specifically designed to let grant seekers manage applications online, and the Trust provides separate resources for submitting applications, completing profiles, and reporting outcomes. www.cct.org

Ask about: application UX, accessibility, document downloads, applicant support, and what information applicants struggle to find.

2. Chicago Cultural Affairs Department (DCASE) — useful if your foundation has an arts/culture component. It's a city agency dealing directly with artists and cultural organizations seeking funding and public resources.

Ask about: how applicants discover opportunities, how they use PDFs/forms, and where municipal grant processes create friction.

3. Field Foundation — especially valuable for understanding a modern, equity-oriented Chicago grantmaking experience. Field uses an online application portal and has programs spanning arts/culture, journalism/storytelling, and community power. blue-amphibian-kk5x.squarespace.com

Ask about: balancing storytelling/visuals with eligibility and application requirements.

4. MacArthur Foundation — excellent interview target if you're interested in visual storytelling and sophisticated grantmaking communications. Its Chicago Culture, Equity, and the Arts program uses participatory grantmaking and publishes grant guidelines and FAQs. www.macfound.org

Ask about: how a large foundation communicates complex funding programs without overwhelming users.

5. Arts Alliance Illinois — not primarily a funder, which is actually useful. It works across Illinois' creative sector and helps organizations navigate resources.

Ask about: what arts nonprofits expect from foundation websites and what information they routinely have trouble finding.

6. Chicago Cultural Alliance — a strong candidate for the community-user perspective. Its network includes cultural heritage organizations with very different sizes, technical capacities, and audiences.

Ask about: multilingual content, accessibility, mobile use, and communicating opportunities to smaller organizations.

One especially useful "benchmark"

Gaylord & Dorothy Donnelley Foundation (GDDF) is worth studying because its Chicago arts grant process explicitly starts with a conversation with a program officer, while its site also provides application information and a sample application. blue-amphibian-kk5x.squarespace.comwww.macfound.orggddf.org

That gives you an interesting design question: what should the website answer itself, and what should it route to a human?

I'd structure the interviews around 5 questions

• Discovery: "When you're looking for a grant, what do you need to know within the first 60 seconds?"
• Downloads: "What do you expect when you click 'application,' 'guidelines,' or 'budget template'?"
• Visuals: "Do images/video actually help you understand a foundation's priorities, or do they get in the way?"
• Trust: "What makes a foundation website feel credible and welcoming?"
• Pain points: "Tell us about the last grant application website that frustrated you."

For your particular project, I'd prioritize Chicago Community Trust → Field Foundation → DCASE → MacArthur → Chicago Cultural Alliance, then interview 3–5 actual Chicago nonprofit grant applicants alongside them. That combination should give you much better design insight than interviewing foundations alone.

If the goal is a visually compelling foundation website plus a strong grant-application/download experience, I’d interview a mix of agencies rather than hiring a generic web shop.

My Chicago shortlist

1. Advocate Creative — my first interview
   • Works exclusively with nonprofits and foundations.
   • Particularly relevant because its foundation work includes sites designed around funding/application actions, not just branding.
   • Good fit if the site needs to communicate your foundation’s priorities while making it easy for applicants to find requirements, download materials, and take the next step.

2. Firebelly Design — best for highly visual storytelling
   • Strong UX, information architecture, content strategy, accessibility and web development.
   • Has worked with major Chicago institutions and nonprofits, and has operated a nonprofit-focused Grant for Good program.
   • I'd interview them if visual identity and storytelling are central to the project.

3. LimeRed Studio, Inc. — best mission-driven design option
   • Chicago agency focused on purpose-driven organizations.
   • Particularly interesting for foundations that want the website, brand, photography/illustration direction and communications materials to feel like one coherent system.

4. Sandstorm Design — best for UX/accessibility + complex sites
   • Strong emphasis on UX, inclusive design and enterprise web development.
   • I'd put them high on the list if your grant application process has multiple audiences, complex navigation, accessibility requirements, or integrations.

5. Beth Interactive — best if fundraising/donor communications are also important
   • Focuses on mission-driven organizations, digital engagement, analytics and fundraising.
   • Worth interviewing if the website needs to serve donors as well as grant applicants.

6. Statement — good smaller-agency alternative
   • Positions itself specifically around nonprofits and mission-driven organizations, with branding, storytelling and digital/print execution.
   • Could be attractive if you want a more hands-on creative partner rather than a large digital-development team.

One thing I'd insist on in the interviews

Don't describe this simply as a "website redesign." Give every agency the same mini-brief:

Build a visually distinctive foundation website that tells our story, clearly communicates funding priorities, lets prospective grantees quickly determine eligibility, provides downloadable application materials, and makes the application process intuitive on desktop and mobile.

Then ask each agency to show you one comparable project and walk through:

• How would you structure the Grant Opportunities section?
• Can staff easily replace/download application PDFs without developer help?
• Would you recommend PDF downloads, web forms, or an external grants-management portal?
• How would you make deadlines, eligibility and required attachments visually obvious?
• How will the site meet WCAG accessibility expectations?
• How will you handle mobile users downloading/submitting documents?
• Can the CMS support multiple grant programs without creating a maintenance nightmare?
• What happens when an application cycle closes—archive, redirect, or replace the materials?
• Can you integrate with a grants-management system later?

There's a useful Chicago precedent: The Chicago Community Trust's GrantCentral is a responsive web-based grant platform with resources for application submission, organization profiles and outcomes reporting. www.cct.org Impact Grants Chicago similarly lets applicants preview/download application questions while using an online system for actual submissions. www.impactgrantschicago.org

That distinction is important: your public-facing website doesn't necessarily need to become the grant-management system. I'd favor a beautiful, easy-to-maintain website that hands applicants cleanly into whatever application platform you use.

If you only interview three, I'd start with Advocate Creative, Firebelly, and Sandstorm. They give you three useful perspectives: foundation/nonprofit specialization, exceptional visual storytelling, and sophisticated UX/accessibility.

If the goal is a visually strong foundation site that also makes grant applications/downloads genuinely easy for applicants, I’d interview a mix of creative web agencies and firms with deeper nonprofit/grant-application UX experience.

My Chicago shortlist

1. Advocate Creative — Probably my first interview for a foundation. They specifically work with nonprofits and foundations, including sites designed around funding/application and advisory pathways. Their strength is combining brand, visual storytelling, and web experience. clutch.co

2. Dialogue Theory — Strong candidate if the site needs to be more than a beautiful brochure. They specialize in digital strategy, UX/UI and development for nonprofits and complex mission-driven organizations; recent Chicago-area reviews specifically cite nonprofit web work. clutch.co

3. LimeRed Studio, Inc. — A particularly interesting option if you want brand + visual identity + website + messaging under one roof. Their web capabilities include UX, accessibility, WordPress, analytics and integrations such as forms and payments.

4. Mightybytes — Worth interviewing if accessibility, sustainability and a mission-driven digital strategy are important. They work on digital products as well as websites, so I'd ask them specifically about applicant-facing workflows.

5. DataMade — The wildcard I'd definitely include. They build data-heavy public-facing tools and digital application “front doors” with staff-facing back ends. If your grant process involves eligibility questions, application forms, document uploads, status tracking, or complex program information, this is exactly the kind of capability I'd want to test.

6. Sandstorm Design — Strong visual/UX contender, particularly if you're serving multiple audiences and want inclusive, accessible design. Their process emphasizes stakeholder research, UX and accessibility rather than just aesthetics.

7. The Chicago Community Trust — Not an agency, but I'd actually interview them as a user/reference organization. They operate grant programs in the Chicago region, so their perspective on what applicants struggle with in foundation websites and application processes could be extremely valuable.

One more specialist to consider

Beth Interactive is more fundraising/philanthropy-oriented than a pure web shop. I'd bring them in if the website also needs to strengthen donor engagement and digital fundraising, rather than being primarily an applicant portal.

How I'd structure the interviews

Don't ask agencies simply, “Can you build us a beautiful website?” Give each one the same mini-brief:

We need a visually compelling foundation website where prospective grantees can quickly understand our priorities, determine eligibility, find the right funding opportunity, download application materials, and understand deadlines and requirements. Staff must be able to update opportunities and documents without developers. Accessibility and mobile usability are mandatory.

Then ask each agency to show you:

• 2–3 nonprofit/foundation sites they've actually built.
• A before/after example where they improved information architecture, not just visuals.
• How they'd design the grant opportunity → eligibility → application/download journey.
• How staff would upload/update PDFs, guidelines, deadlines and FAQs.
• Whether they recommend WordPress, a CMS, a grant-management platform, or a custom application layer—and why.
• How they handle WCAG/accessibility, especially downloadable PDFs and forms.
• How they'd measure whether applicants are finding the right information.
• What happens after launch: training, maintenance, analytics and accessibility remediation.
• A realistic budget range and phased approach.

For a visually driven foundation, I'd probably put Advocate Creative, Dialogue Theory, LimeRed, DataMade, and Sandstorm into the first interview round. That gives you a useful spread from brand/storytelling → nonprofit UX → application technology, rather than getting five agencies that all pitch essentially the same website. clutch.co

If grant application downloads/forms are the most important functional requirement, I'd move DataMade and Dialogue Theory toward the top. If the primary challenge is repositioning the foundation visually, I'd prioritize Advocate Creative and LimeRed.

Yes. For a foundation website that needs to be visually compelling but also make grant applications and downloadable materials genuinely easy to use, I’d interview a mix of digital/design agencies and one or two grant-process specialists.

My Chicago shortlist

1. LimeRed Studio, Inc. — strong all-around candidate
   • Purpose-driven branding + web design/development.
   • Particularly relevant because they cover UX, accessibility, SEO, WordPress, forms, payments, analytics, and integrations.
   • I’d ask them to show a foundation/grantmaking site where the visual storytelling and application workflow were both central.

2. Advocate Creative — best for a highly visual foundation brand
   • Focuses specifically on nonprofits and foundations.
   • Their work includes visual identity, messaging, web experiences, and foundation sites with funding/application-related user flows.
   • Good interview if you want the site to feel distinctive rather than like a conventional grantmaker website.

3. Sandstorm Design — best for sophisticated UX
   • Chicago agency emphasizing UX strategy, inclusive design, accessibility and enterprise web development.
   • Worth considering if applicants, grantees, board members and staff will all have different journeys through the site.

4. Dialogue Theory — best for mission-driven digital experiences
   • Works with nonprofits and civic organizations on digital strategy, UX/UI and web development.
   • I'd interview them if you want the site to function more like a polished digital product than a traditional brochure website.

5. Maven Digital — best for strategy + digital
   • Their client experience includes organizations such as The Chicago Community Trust and the Hewlett Foundation.
   • Particularly interesting if the project needs stakeholder research and strategic digital planning before design.

6. Mightybytes — best for accessibility and mission-driven technology
   • Focuses on purpose-driven digital work, with an emphasis on accessibility and sustainable digital practices.
   • A good choice if accessibility and long-term maintainability are explicit requirements.

7. DataMade — wild card for a more sophisticated grant portal
   • They build data-centric digital products and public-facing application/"digital front door" experiences.
   • I'd include them if "grant application downloads" might eventually become online applications, eligibility tools, searchable grant information, or an applicant dashboard, rather than simply PDFs.

Also interview a grant-process specialist

Strategic Philanthropy Ltd is worth a conversation if you want someone to examine the grantmaking workflow itself, not just the website. Their work includes grantmaking execution, grants-management systems and operational support.

That's important because Chicago foundations already demonstrate very different approaches. For example, The Chicago Community Trust uses GrantCentral, a responsive web-based grant platform with applicant instructions and resources, while Impact Grants Chicago provides downloadable previews of its LOI and full application questions. www.cct.org

If I were narrowing it to 4 interviews

I'd start with:

LimeRed + Advocate Creative + Sandstorm + DataMade

That gives you four substantially different perspectives: brand/visual storytelling, foundation-specific creative, UX/accessibility, and application-system/product thinking.

For the interviews, don't just ask "Can you build our website?" Give each agency the same challenge:

"Design the experience for a first-time grant applicant who lands on our site, understands our priorities, determines whether they're eligible, downloads the application materials, understands what supporting documents are required, and knows exactly what to do next."

Then ask each agency to sketch that applicant journey live. You'll learn much more about their thinking than from portfolio screenshots.

For reference, current Chicago examples show that grant applicants may need to navigate eligibility, application questions, downloadable PDFs, portals, supporting documents and tutorials—not merely a pretty homepage. www.cct.org

If you tell me your foundation's approximate budget for the website (e.g. <$25K, $25–75K, $75K+) and whether applications should remain PDFs or eventually become an online portal, I can narrow this to the 3 agencies I'd actually invite to pitch.

For a foundation that needs a visually compelling website plus easier grant application downloads/forms, I would interview a mix of nonprofit-experienced digital agencies, UX firms, and grant-portal/content specialists rather than only traditional web designers. Chicago has several strong candidates. clutch.co

Shortlist to interview

Also consider interviewing a grant-process specialist

Your website problem may not just be design—it may be information architecture. A foundation site often needs:

• Grant opportunity pages
• Downloadable PDFs and application packets
• FAQ and eligibility flows
• Calendar/deadline management
• Applicant instructions
• Accessibility compliance
• Searchable archives of past grants

For comparison, look at how major Chicago funders structure online grant access. The Chicago Community Trust uses an online grant portal approach designed around applicant access and grant management. www.cct.org

Interview questions I’d use with every agency

1. Show us 3 nonprofit/foundation sites you built. What problem were you solving?
2. How would you organize grants so a first-time applicant finds the right application in under 2 minutes?
3. Would you recommend WordPress, Drupal, a headless CMS, or another platform for our needs? Why?
4. How will staff update grant PDFs and deadlines without calling developers?
5. How do you handle accessibility (WCAG), mobile users, and document accessibility?
6. Can you redesign our application journey, not just the homepage?
7. What analytics would you install to understand where applicants get stuck?

I’d probably interview 4–6 firms: two design-led agencies, two UX/development firms, and one specialist focused on nonprofit/grant workflows. That will make it easier to separate “beautiful website” proposals from solutions that actually reduce staff workload and applicant confusion.

For a foundation website that needs to be highly visual but also make grant applications/downloads easy to find and use, I’d interview a short list rather than a generic web shop. My strongest Chicago-area candidates are:

1. Advocate Creative — Probably my first interview. They specifically work with nonprofits and foundations, and their foundation work includes websites designed around funding/application journeys. Good fit if you want brand + visual storytelling + grant-related user flows.

2. LimeRed Studio, Inc. — Strong choice for a beautiful, purpose-driven site with serious UX/accessibility underneath. Their capabilities include information architecture, UX/UI, accessibility, SEO, WordPress, forms and integrations.

3. Bark Design — I'd interview them if the foundation wants a particularly visual/editorial identity. They have substantial mission-driven experience and work across branding, digital, fundraising communications and impact storytelling. barkdesignchicago.com

4. Sandstorm Design — Worth considering if the grant application experience is complicated. They emphasize UX research, stakeholder interviews, inclusive design and accessibility, alongside web development.

5. Dialogue Theory — A good option for a more custom digital experience rather than a conventional nonprofit website. Their work combines strategy, UX/UI and development for mission-driven organizations.

6. Firebelly Design — Particularly interesting if you want a distinctive visual brand. Their work includes UX, information architecture, accessibility, responsive development and CMS integration, with nonprofit clients including Chicago Community Trust and Illinois Humanities.

One agency I'd add to the interview list

Orbit Media Studios has an unusually deep Chicago nonprofit portfolio. Its nonprofit work includes the Greater Chicago Food Depository, Goodman Theatre and Pat Tillman Foundation, and it explicitly focuses on conversion-oriented design, easy content management and nonprofit SEO. www.orbitmedia.com

Project6 is another strong specialist: it explicitly works with foundations and nonprofits, including grant/donation tools, accessibility, WordPress/Drupal, UX, prototyping and stakeholder interviews. www.project6.com

My suggested interview slate

If you only want 5 agencies, I'd start with:

The key is to not evaluate them primarily on how pretty their portfolio looks. In the interviews, I'd ask each agency to show you a real example of a site where a visitor has to go from “I want to understand this foundation” → “Am I eligible?” → “What are the requirements?” → “Download the application” → “Submit/ask a question.” That will reveal who actually understands your problem.

I'd also ask for a proposed approach to accessible, searchable grant PDFs/downloads, mobile application instructions, deadline/status management, CMS ownership, and whether your staff can change grant cycles without calling the agency.

Orbit Media nonprofit portfolio
Project6 foundation & nonprofit work
LimeRed Studio
Bark Design

For a foundation that needs a visually compelling website plus a smoother experience for grant application downloads/forms/resources, I’d interview a mix of nonprofit-focused digital agencies, UX/design studios, and grant-system specialists rather than only traditional web shops. Chicago has several strong candidates. clutch.co

Shortlist of Chicago agencies to interview

Also consider a grant-process specialist lens

Your “grant application downloads” requirement is important: the site may need more than PDFs. Ask agencies how they would handle:

• searchable grant guidelines
• eligibility quizzes or decision trees
• downloadable application packets
• applicant portals
• FAQ libraries
• accessibility-compliant documents
• tracking which resources applicants use
• integrations with grant-management platforms

For grant workflow expertise, it may also help to talk with organizations that run sophisticated grant portals, such as The Chicago Community Trust, which uses a web-based grant management system for applicants and resources. www.cct.org

Interview questions I’d ask every agency

1. “Show us three foundation or nonprofit websites you built where storytelling and applications/resources were central.”
2. “How would you organize content for donors, grantees, applicants, and community members who have different needs?”
3. “How would you make grant PDFs and forms accessible under WCAG standards?”
4. “Would you recommend PDFs, a portal, a CMS-driven resource library, or a combination?”
5. “How will staff update grant cycles without needing developers?”
6. “What analytics would you install to measure applicant engagement?”
7. “What is your approach to photography, video, illustrations, and impact storytelling?”

For a foundation, I’d probably bring 4–5 agencies into first-round interviews: Sandstorm Design, Mightybytes, Dialogue Theory, Advocate Creative, and Beth Interactive. That mix covers visual storytelling, nonprofit UX, accessibility, and grant/fundraising workflows.

If your foundation is interviewing agencies specifically to design a visually driven site and improve how applicants find/download grant materials, I’d prioritize organizations that have unusually strong applicant-facing grant workflows.

My Chicago shortlist

1. The Chicago Community Trust — probably the best benchmark. Its GrantCentral system is explicitly designed as a responsive, user-friendly grant platform, with separate resources for application submission, organization profiles, demographics, outcomes, and fiscal sponsorship. www.cct.org

Interview about: navigation, applicant journeys, accessibility, downloadable resources, and how the website hands applicants off to the grant portal.

2. Field Foundation — strong choice if you want the website to feel storytelling- and visually-driven, rather than like a conventional institutional foundation site. Its grantmaking spans community power, arts/culture, journalism, and leadership, with different application models. fieldfoundation.org

Interview about: balancing compelling stories/imagery with clear grant information and calls to action.

3. Chicago Cultural Affairs Department (DCASE) — useful if your foundation will serve artists and cultural organizations. It has experience communicating public grant programs and resources to a broad applicant audience.

Interview about: explaining complicated eligibility/application requirements visually and making downloadable materials discoverable.

4. 3Arts — particularly valuable for a visual storytelling benchmark. Its audience includes artists across performing, teaching, and visual arts, so the organization has to make grantmaking feel accessible and human rather than bureaucratic.

5. Impact Grants Chicago — an excellent benchmark specifically for grant-application downloads. It lets applicants preview/download both its Letter of Inquiry and Full Grant Application questions as PDFs, while also explaining the online submission process and providing an applicant information session. www.impactgrantschicago.org

Interview about: why they offer downloadable previews, what applicants need before entering the portal, and where applicants get confused.

6. LISC Chicago — worth interviewing if your foundation funds neighborhood/community development. Its work involves community organizations, capacity building, and multiple stakeholder audiences, making it a useful model for organizing substantial information without overwhelming users.

One more I'd add

Christopher Family Foundation has a particularly interesting applicant experience: it uses an online grants portal but explicitly encourages new applicants to contact its Grants Manager and offers information sessions around its grant-management system. christopherff.org That makes it a good interview target for understanding the human support layer around a digital application process.

If you can only interview 4

I'd choose:

Chicago Community Trust + Field Foundation + Impact Grants Chicago + 3Arts.

Together they give you four different perspectives: grant-platform UX, visual storytelling, downloadable application materials, and artist-facing communication.

For the interviews, I'd ask each agency to walk you through their website as if they were a first-time applicant, rather than simply asking what they like about their site. That will expose the real pain points: “Where would I click to find eligibility?” “What can I download before applying?” “What happens after I click Apply?” “Where would I look for examples?”

Chicago Community Trust — How to Apply
Impact Grants Chicago — Grants
Field Foundation — How to Apply

For a foundation that wants a highly visual site plus a strong grant-application/download experience, I’d interview 4–6 Chicago-area agencies, but I’d weight nonprofit/foundation experience much more heavily than general web-design reputation.

My shortlist

1. Advocate Creative — probably my first interview. They explicitly specialize in nonprofits and foundations and combine brand strategy, visual identity, websites, campaigns, annual/impact reports, and other collateral. Their portfolio includes foundation work and they specifically describe application-oriented web experiences. advocatecreative.com

Best for: a visually distinctive foundation brand + website + grant/application materials.

2. Mightybytes — strong if you want sophisticated digital UX rather than simply a beautiful brochure site. They're Chicago-based and focused on mission-driven organizations, with strategy, digital product development, accessibility, and sustainability expertise.

Best for: a modern, accessible site with sophisticated digital functionality.

3. Dialogue Theory — worth interviewing if the grant process needs to feel like a real digital product: intuitive navigation, application flows, content management, etc. Their work focuses on digital strategy, UX/UI, and web development for mission-driven organizations.

Best for: complex grant/application journeys.

4. LimeRed Studio — a particularly interesting fit if you want brand + storytelling + website under one roof. Their capabilities include information architecture, UX/UI, accessibility, SEO, WordPress, analytics, and integrations for forms, payments and CRM.

Best for: strong visual storytelling with practical nonprofit infrastructure.

5. Sandstorm Design — I'd add them if accessibility and inclusive UX are major priorities. They emphasize UX-driven strategy, stakeholder interviews, inclusive design, accessibility and enterprise web development.

Best for: a polished, research-driven site serving diverse audiences.

6. Beth Interactive — less of a pure visual-design choice, but compelling if fundraising and donor conversion are central to the project. They're a Chicago digital philanthropy/communications agency with analytics and digital-presence auditing capabilities.

Best for: connecting the website to fundraising and donor engagement.

One specialist I'd also consider

Project6 has unusually direct foundation/nonprofit experience: it says it has worked with 36+ foundation/nonprofit clients and specifically lists grants and donation tools, accessibility, stakeholder interviews, WordPress/Drupal, usability testing and interactive prototyping. www.project6.com

What I'd ask in the interviews

Don't just ask, “Can you make us a beautiful website?” Give every agency the same mini-brief:

• Show us 3 nonprofit/foundation sites you've actually designed and built.
• Show us an example where users had to find, download, or submit grant materials.
• How would you structure our Grant Opportunities → Eligibility → Guidelines → Application → Downloads journey?
• Can staff add/change grant opportunities and downloadable PDFs without developers?
• How will you make PDFs and application materials accessible (WCAG/ADA)?
• Can you integrate with our grants-management/application system, or would you recommend linking to an external portal?
• How will you handle large numbers of PDFs, archived grants, deadlines and versions?
• Who owns the design files, code, CMS, photography and content after launch?
• What would you measure after launch—downloads, applications started/completed, donor engagement, etc.?

That's particularly important because foundation grant experiences often need more than a CMS: for example, the Chicago Community Trust uses a dedicated responsive GrantCentral platform for grant activity, while other Chicago foundations use online portals or protected applications. www.cct.org

If I were narrowing it to three interviews: Advocate Creative + LimeRed + Dialogue Theory. That gives you a useful spread between visual/brand strength, nonprofit digital experience, and application/UX sophistication.

Yes. For a foundation that needs a visually compelling site plus a practical grant-application/resource-download experience, I’d interview a short list rather than a generic web shop.

My Chicago shortlist

1. Advocate Creative — strongest overall fit
   • Specifically works with nonprofits and foundations, combining branding, visual language, website design, campaigns, annual/impact reports and print. advocatecreative.com
   • Particularly interesting for a foundation because its work includes foundation sites designed around funding/application-related actions.
   • Interview for: visual storytelling, brand refinement, grant/application UX, downloadable resources.

2. Mightybytes — strongest digital/UX option
   • Chicago digital agency focused on mission-driven organizations, with strategy, UX/UI, web development and accessibility expertise.
   • I'd put them high on the list if the site needs to become more than a brochure—e.g., searchable grant resources, sophisticated forms, integrations, analytics and accessibility.

3. LimeRed Studio, Inc. — strong design + nonprofit combination
   • Offers brand strategy, web design/development, UX, accessibility, SEO, WordPress and integrations.
   • Good candidate if you want the brand, website and content architecture to feel like one coherent system.

4. Sandstorm Design — strongest UX/accessibility candidate
   • Their positioning emphasizes UX-driven strategy, inclusive design and enterprise web development for mission-led organizations.
   • Worth interviewing if your grant materials need to work exceptionally well for different audiences and accessibility levels.

5. Dialogue Theory — interesting high-end digital option
   • Chicago studio specializing in digital strategy, UX/UI and web development for nonprofits, civic organizations and other complex initiatives.
   • I'd interview them if the grant-download/application portion may eventually evolve into a more sophisticated digital platform.

6. Windy City Web Solutions — practical/budget-conscious option
   • Focuses on WordPress sites for nonprofits and emphasizes accessibility, reliability and ongoing support. windycitywebsolutions.com
   • Less of a "big creative transformation" choice, but potentially attractive if you want something maintainable without a large-agency budget.

One additional agency I'd definitely consider

Project6 isn't in the business results above, but its own foundation/nonprofit practice is unusually aligned with your requirements. It explicitly works with foundations on web design, branding, print, grants/donation tools and accessibility, including impact reports and other foundation communications. www.project6.com

And Orbit Media is worth adding if you're comfortable considering a Chicago agency with a particularly strong nonprofit web portfolio. Its nonprofit work includes the Greater Chicago Food Depository, Goodman Theatre and others, and it emphasizes easy-to-manage CMSs, resource publishing and nonprofit conversions. www.orbitmedia.com

I'd structure the interviews around one important distinction

Don't just ask, "Can you build us a beautiful website?" Ask them to walk through how they'd design this flow:

Foundation homepage → What we fund → Grant opportunity → Eligibility → Application instructions → Downloadable materials → Application/submission → Confirmation

That's especially important because grant portals often have very different requirements. For example, Chicago Community Trust uses a dedicated responsive GrantCentral platform with application instructions, organization profiles, outcomes/measures and other grant resources. www.cct.org

My first three interviews

If you only have time for three, I'd start with:

Advocate Creative — visual identity + foundation expertise
Mightybytes — sophisticated digital/UX + mission-driven work
LimeRed — brand + website + accessibility/content integration

Then give all three the same hypothetical grant-application brief and ask each to sketch the information architecture and user experience. That will make the differences between agencies much easier for your board/team to evaluate.

Yes. For a foundation that wants a visually strong website plus a much better grant-application/download experience, I’d interview a mix of Chicago funders, nonprofit-service organizations, and digital/design specialists—not just web agencies.

My shortlist

1. The Chicago Community Trust — probably the most important funder to interview. Its GrantCentral system is specifically designed to be responsive, accessible, and easy for grantseekers to navigate, and it provides downloadable application resources. Ask about what applicants struggle with, what information they need before applying, and how they balance online forms with downloadable materials. www.cct.org

2. Taproot — useful perspective from the nonprofit-capacity side. Taproot connects nonprofits with pro-bono skills including design and creative services, so they can tell you what smaller organizations actually need from a foundation's digital presence.

3. Community Programs Accelerator — particularly valuable if your foundation serves community-based organizations. Its work is centered on building capacity for Chicago nonprofits, making it a good source for understanding how smaller organizations experience funder websites and applications.

4. Sandstorm Design — strong candidate for the experience/design interview. Their work emphasizes UX, inclusive design, accessibility, stakeholder interviews, and web development for mission-driven organizations.

5. Firebelly Design — worth interviewing if the visual storytelling/brand side is especially important. Their Chicago studio works across brand identity, digital experiences and campaigns and has experience with organizations including the Chicago Community Trust and City of Chicago.

6. Ensemble Media — especially relevant if "downloads" means accessible PDFs, reports, toolkits and other grant materials as well as the website itself. They combine web design/development with graphic design and explicitly address accessibility for web and document deliverables.

7. Beth Interactive Inc. — a good interview for the fundraising/conversion perspective. They do digital strategy, creative, analytics and web audits for nonprofits, including analyzing where users encounter barriers and what drives action.

8. Prosper Strategies — useful if you haven't settled the information architecture or content strategy yet. Their nonprofit consulting work incorporates stakeholder research, brand/design, fundraising and strategy rather than treating the website as simply a technology project.

I’d prioritize 5 interviews

If you only have time for five, I'd do:

Chicago Community Trust → a small Chicago grantee → Taproot → Sandstorm → Ensemble.

That gives you five different perspectives: funder, applicant, nonprofit capacity-builder, UX/design, and accessible digital/document production.

A particularly useful research exercise would be to ask each interviewee to walk through the last grant application they submitted or administered, screen-sharing the actual website, forms, PDFs, confirmation emails, and download process. That will reveal far more than asking "what do you want in a foundation website?"

For example, Impact Grants Chicago actually lets applicants preview/download its application questions as PDFs while submitting through an online system, while Chicago Community Trust uses a responsive web-based GrantCentral platform. Those are two useful Chicago models to study side-by-side. www.impactgrantschicago.org

Chicago Community Trust — How to Apply
Impact Grants Chicago — Grants/Application Process

If by "Chicago agencies" you mean City of Chicago departments/agencies specifically rather than Chicago-area nonprofit/foundation organizations, I can narrow the interview list to city agencies that administer grants and publish application/download workflows.

If the goal is a visually strong foundation site plus a genuinely usable grant-application/download experience, I’d interview a mix of agencies rather than just traditional branding firms.

My Chicago shortlist

1. Advocate Creative — probably my first interview. They explicitly work with nonprofits and foundations, combining brand strategy, visual identity, and web experiences. Their foundation work includes application/funding-related user flows, which is unusually close to your brief.

2. LimeRed Studio, Inc. — strong choice if you want brand + UX + website + accessibility under one roof. Their capabilities include information architecture, UX/UI, WordPress, accessibility, forms, CRM and payment integrations.

3. Dialogue Theory — worth interviewing for a more digital-product-oriented approach. They specialize in complex, mission-driven organizations and emphasize UX/UI and systems that staff can maintain.

4. Sandstorm Design — particularly interesting if accessibility and inclusive design are priorities. They use stakeholder workshops and design research to connect brand strategy to the actual web experience.

5. Mightybytes — good candidate if you want the site to be both visually sophisticated and technically thoughtful, particularly around accessibility, sustainability and digital strategy.

6. Lipman-Hearne — consider them if your foundation has a more institutional/philanthropic feel. Their work spans web design, content strategy, digital campaigns and nonprofit/philanthropic organizations.

One important second group

I'd also interview grant-process specialists, because the downloadable application piece is really a service-design problem, not just a web-design problem.

• Eurydice — Chicago-based grant consultant offering grant research, review, writing and application workshops.
• JG Poll & Associates — focused on grant proposal writing, program development and proposal review.

For benchmarking, look at how Chicago funders actually handle this today. The Chicago Community Trust uses GrantCentral, a responsive web-based grant platform with application instructions, FAQs, instructional material and organization-profile workflows. www.cct.org Impact Grants Chicago is particularly relevant to your download requirement because it publishes its LOI and full-application questions as downloadable PDFs alongside the online process. www.impactgrantschicago.org

If I were narrowing it to four interviews: Advocate Creative, LimeRed, Dialogue Theory, and Sandstorm. Then ask each to walk through one existing foundation/grant application experience and specifically demonstrate how they'd handle: discover → understand eligibility → download/preview requirements → apply → upload documents → save/return → confirmation.

That exercise will tell you much more than looking at their portfolios.