Stephen Carroll-Keene

Founding mentor

🌱 First session

Product Designer @ EverDriven

Colorado Denver (UTC-6) 4 yrs in design

About

I pivoted into design the long way around — a tenured retail career, then a failed run at front-end development, and (thanks to 2020) finally into UX/UI by way of a design bootcamp and certificate. No CS degree, no traditional path: I landed my first design role in 2023 and I'm a Product Designer today. What I've gone deep on in a short time: designing B2B SaaS enterprise products, building accessibility into how a team actually ships (WCAG audits and VPATs, remediation, getting products certified for the customers that require it), and working out where AI genuinely helps a design workflow versus where it just gets in the way. If you're coming into design from an "unrelated" career, I've lived that exact transition recently enough to still remember what's confusing about it.

How I can help

- Breaking in from a non-traditional background (retail, service, ops, self-taught) and want to frame that experience as an asset, not a gap to apologize for. - Early-career and want a real portfolio/case-study review — I'll tell you how it reads to the people actually doing the hiring, not just "looks nice." - Curious about accessibility — what WCAG/AA actually means, how to design for it by default, and why it's one of the strongest career differentiators going right now. - Trying to use AI without it flattening your craft — where it speeds you up, where it quietly hurts, how to keep judgment in the loop. - In (or aiming at) B2B SaaS / enterprise / data-dense products and want to talk through that less-glamorous-but-in-demand corner of design. Bring a specific thing you're stuck on: a portfolio, a project, interview prep, or just an "is this normal?" gut-check on the messy in-between and we'll work it live.

Ask me about

Pivot into design

A failed launch

A reorg

Stakeholder standoffs

Negotiating comp

Building a design system

Getting passed over

Imposter syndrome

Influence without authority

Craft to strategy

Presenting to execs

Accessibility & WCAG

AI in Design Workflows

Not the right mentor for: Deep user-research methodology, people management or director-level career moves, illustration or motion design, freelance or agency business development.

A hard problem I've navigated

When the 2020 pandemic killed my plan to move into front-end dev, I was working retail with some self-taught UI skills and no design degree. I bet on a UX certificate and spent almost two years getting rejected before landing my first role in 2023. What I took from it: your "unrelated" background isn't the liability you think it is. The years I spent reading people across a sales counter and walking them through setting up their mobile devices turned out to be user research and usability tests that I didn't even know I was doing. I can help you find and name those transferable threads instead of hiding them.

Frequently asked

Can I break into design without a traditional design degree?

I did without a CS or design-adjacent degree; I went the bootcamp-certificate route, and it still took almost two years of persistence before I landed my first role in 2023. I'm upfront about that timeline because the "3-6 months to UX!" promise is exactly what sets people up to feel like failures. It's doable, but it's a grind, and I can tell you what actually moved the needle versus what wasted my time.

Is it even worth trying to break in right now, with AI and junior roles drying up?

As we all know, the entry-level job market in tech is brutal. Junior roles are scarce and a single opening can pull hundreds of applicants. But it's not hopeless; it's just different. AI didn't replace designers, it made generic output cheap so the way in now is to be specific and hard to ignore in a lane (accessibility, AI product design, SaaS/enterprise), and to show you can direct AI and tie design to outcomes, not just make nice screens.

How do I talk about my non-design background without it sounding like a weakness?

Your past career is almost always transferable, you just have to translate it into design language. Bring me your background and the roles you're targeting and we'll find the threads that make you more interesting, not less. I spent over a decade in retail, it's definitely possible to connect the dots.

Will you actually review my portfolio or case study?

Yes! Send it ahead of time and I'll come with specific notes. I'll tell you how it reads to the people doing the hiring: where a recruiter's eyes glaze, where your story's buried, what to honestly cut out.

I'm brand new to design, am I too early to book you?

Not at all. Early-career folks and career-changers are exactly who I'm here for. "Is this normal?" and "what do I even do next?" are completely fair thoughts to bring along.

Do I need to know accessibility to get hired?

In my experience, it helps a lot — and almost no early-career designers can speak to it, so it's a real differentiator. I've built accessibility into how a team ships (audits, VPATs, remediation), and I can give you the practical basics that make you stand out without having to become an expert overnight.

What should I prep before our session?

Come with one specific thing you're stuck on: a portfolio, a project, an upcoming interview, or a decision you're wrestling with. The more specific, the more useful I can be. If it's a portfolio review, send the link ahead of time.

How should I think about AI in design?

learn to drive it. I use AI as a tool to speed up parts of my workflow without letting it flatten the craft or the judgment, and to make working with developers and engineers easier. I'll show you where it genuinely helps, where it quietly hurts, and how to talk about it in interviews.

Expertise

UX Designer

Product Designer

Gaming

B2B SaaS

AI workflows

AI tools

Agentic AI

Accessibility

Career Change

Experience

Product Designer · EverDriven
January 2026 - Present
Established EverDriven's accessibility program from scratch - conducted WCAG 2.1 A/AA testing on our VIP mobile app via VoiceOver and TalkBack, authored the company's first VPAT (VPAT 2.5 Rev, WCAG Edition), and increased Level AA conformance from 65% to 85% ahead of a company OKR deadline. Navigated a dual-product compliance response to a school districts' HB21-1110 questionnaire - driving remediation for our VIP mobile app while defining a transparent disclosure and sunset strategy for one web product ahead of its replacement launching. Both the submitted VIP mobile app VPAT and HB-21 questionnaire response were district approved on June 26, 2026. Built a three-tier remediation roadmap across 41 issues and 18 failing WCAG 2.1 criteria for our VIP mobile app, coordinated sprint execution with the mobile engineering team, and drove all tiered issues to resolution by the school-year code freeze - satisfying a company OKR KR 2.1.1.3 ahead of the June 30th deadline. Stood up as EverDriven's interim accessibility lead while the company's cross-functional accessibility committee was established - coordinating compliance responses across Product, Engineering, QA, Legal, Customer Success, and executive leadership simultaneously. Designed and demonstrated a proof-of-concept Figma-to-Storybook pipeline using Claude as a governance enforcer - with WCAG 2.1 A/AA compliance and design token adherence built into the orchestration layer as non-negotiable requirements, not post-hoc checks. Holds DHS Trusted Tester certification (TT-2412-05241, issued Dec 2023) — the formal credential underlying all VPAT testing conducted for VIP, TripCentral, and Driver/SafeRoute.
Associate UX/UI Designer · Accruent
August 2023 - December 2025
My role had evolved to focus on leading the design for a critical greenfield initiative, where I own the UX/UI process from concept to handoff. This includes conducting user research to uncover insights and partnering with key stakeholders to validate, defend and champion design decisions. I collaborate closely with respective PMs, engineering and architecture teams to define technical requirements. I collaborate with a team of designers to create a consistent user experience across a wide range of assets and facilities products. I am DHS Trusted Tester Certified (508 and WCAG 2.2 AA Accessibility Standards) and actively contribute to implementing accessibility across all our products. I also contribute to various facets of our Design System such as components, accessibility, usability and technical limitations. Additionally, I maintain an up-to-date understanding of new technologies and best practices through the use of various training tools and services.
UX/UI Designer (Contract) · Robileware
July 2022 - August 2023
Converted components and other assets for the company as we transitioned from Adobe XD to Figma. Created mockups for development handoff. Conducted research alongside the lead designer and tracked ux related deliverables to back future design implementations. Established a design system to speed up implementation of new screens efficiently as we work through sprints in a more streamlined manner alongside development and product.

Also here to learn

Stephen mentors on Hop and is growing too. A bit about their own path right now.

Working on

How to continue to grow and show that I function at a senior designer level. How to garner better communication cross-functionally when needing artifacts from other stakeholders. How to ensure that not only design, but every facet of an org takes accessibility from a business standpoint seriously.

Growing toward

A dream role would be working for notion, Whoop, or potentially shifting into UX game design. Working for a company with a cause that improves other people's lives with effects that are seen almost immediately is extremely gratifying.

Could use a hand with

Building a design system, Influence without authority