Senior Product Designer · Chicago, IL

Design-minded.
Results-focused.

10+ years of using design to drive real business outcomes.

Who I am

About

I've spent 10+ years leading product design end to end across SaaS, enterprise, and startup teams, and I still love the craft as much as day one. Here's what I bring to a team:

01 / AI-native designer

Designs for AI, and with it.

Brings AI into every stage of the design process, from ideation and concepting to high-fidelity work and code-backed prototypes, so ideas turn into something people can get their hands on and react to far sooner.

Practical example: At SeeSaw Labs, I owned end-to-end design of AI-powered products for internal operations and enterprise clients. I validated directions quickly in Figma Make and Claude Design before committing to high-fidelity work, then built code-backed prototypes in Claude Code so users could test real functionality instead of static screens. Along the way, I mentored designers on bringing AI-assisted workflows into their own process.

02 / Systems-minded

Builds the shared language, not just the screen.

Turns scattered UI decisions into a system everyone can point to, and defends it after launch.

Practical example: At Strata Decision Technology, I identified and led a brand refresh and design-system rollout for a SaaS platform used by major healthcare systems, backed by qualitative and quantitative user research, so every team was building from the same source of truth.

03 / Accessible by default

Treats WCAG as a baseline, not a checkbox.

Accessibility gets built in at the wireframe, not patched on before ship.

Practical example: Every curriculum and every student project I oversaw at Flatiron had to meet WCAG accessibility standards, not as a final review step, but as part of how the work got built from day one.

04 / Plainspoken teacher

Makes the process legible to the whole room.

Years spent turning product design into curriculum means the explanation is never the weak link.

Practical example: Years as a Senior Product Design Instructor at Flatiron School, plus a custom design-training program built for active-duty soldiers at the U.S. Army Software Factory, taught me how to make complex product thinking land for a room that's never seen a wireframe.

05 / Strategic operator

Understands the business and technical side of digital products.

Pitches new business, keeps the team on track to deadlines, and does the design work firsthand.

Practical example: At both SeeSaw Labs and Slide UX, I've been heavily involved in the sales process for new client engagements, and I've owned projects from the PM seat: leading the team against milestones and deadlines, keeping clients closely informed on progress, and spotting opportunities to grow further into an account for real business impact, all while executing the design work myself as part of the product team.

Off the clock

Outside of work, I'm still building things. A lifelong football habit (college, pro, fantasy) has turned into more side projects than I can count. Each summer, my wife and I grow a garden and turn the harvest into hot sauce for friends and family. And most nights, I come up with a silly little song and play it on guitar for my dog before bed. I'm convinced he demands this of me, so it's a lot more pressure than you'd think.

Career

Experience

Aug 2024 — Sep 2026
Chicago, IL (Remote)

Owned end-to-end design of AI-powered products for internal operations and enterprise clients, from discovery research and stakeholder interviews through launch. Validated directions quickly in Figma Make and Claude Design, then designed wireframes, high-fidelity prototypes, and accessible design systems in Figma. Built code-backed prototypes in Claude Code to show real functionality, tested them with users, and handed off annotated specs. Managed design and delivery for cross-functional agile teams and mentored designers on AI-assisted workflows.

Oct 2024 — Jul 2026
Chicago, IL (Remote)

Owned UX/UI design for new client engagements from discovery through final delivery. Turned user and stakeholder research into scoped design plans, led information architecture, ideation, and wireframing for websites and web apps, and built interactive Figma prototypes that were tested with users and refined. Also scoped and sold new engagements, carrying projects from the first discovery call through proposal and kickoff.

Apr 2019 — Apr 2024
Chicago, IL (Remote)

Promoted from UX/UI Design Instructor (2019) to Senior (2021), designing and teaching product design and front-end curricula. Built and led a custom product design program for the U.S. Army Software Factory (2020–2021), training active-duty soldiers. Coached students and client teams through research, wireframing, prototyping, testing, and handoff, and ensured curricula and student work met WCAG accessibility standards.

Jul 2017 — Apr 2019
Chicago, IL

Owned the design process for SaaS products turning healthcare big data into clear visualizations, often as the sole designer. Ran qualitative and quantitative research and delivered journey maps, wireframes, prototypes, and annotations. Initiated and led a company brand refresh and design system rollout.

Dec 2016 — Jul 2017
Chicago, IL

Owned client and internal projects from scoping through handoff, including user research, information architecture, and prototype testing.

Case studies

Featured Work

2026 Rendevor

Standardizing Audits Across 70+ Facilities with AI

Standardized a black-box audit process across 70+ dialysis facilities nationwide, some restricted to paper-only workflows, into a single system that works whether an audit happens on a device, in Excel, or on paper. Added an AI handwriting-recognition layer so paper-only sites could upload a scan instead of re-keying it by hand, cutting manual audit entry by 80% and giving leadership real visibility into audit status and findings for the first time. Led design and product management on the project end to end.

Figma Claude Code Excel Anthropic API

View case study → 2025 Cogent Analytics

Enhancing Lead Generation through Custom Web Tools

Led a website redesign and rebuild on WordPress for Cogent Analytics, a consultancy for small business owners with a dated site and an immature CRM, whose executive suite wanted better qualified leads. As client-facing project lead, while a designer and developer focused on the site, I designed and built the two tools at the center of Cogent's new-client campaigns: an ungated Business Valuation Calculator and an 80+ question Business Assessment that turns an owner's answers into a custom playbook. I also built a new HubSpot environment to capture their leads and did development on the site. In the first quarter after launch, qualified leads rose by more than 100%.

Figma Figma Make WordPress Claude Code HubSpot

View case study → 2026 CFBDepth.com

Using AI to Make Complex Data Accessible to Everyone

Led the project and designed CFBAI, an AI chat agent that lets CFBDepth's fans, bettors, and subscribers ask for college football data in plain English, where staff couldn't build every view users wanted. I designed the conversations and the agent's personality, built the chat experience, and gave the agent a memory of each user's teams, data preferences, and betting factors. Alongside it, I designed the internal tool that issues and rotates keys for a new data-licensing API. Both launched before Week 0 of the college football season, bringing in new users at higher price points and a new revenue stream, with a handful of API customers before the final API tool handoff.

Figma Claude Code Vercel Railway Docusaurus

View case study → 2024 Huddl

Streamlining REMS Drug Care Through Connected Pharmacy Workflows

Led research and design on Huddl, a tool that streamlined how pharmacists get educated and registered to distribute REMS drugs, which carry special handling protocols, while giving pharmacists, physicians, and care teams a direct line to patients for prescription renewals, questions, and delivery or pickup confirmations. I ran research with users and subject matter experts, synthesized the findings into opportunities, then led ideation, prototyping, and the development team through launch on TestFlight. Huddl cut administrative hours managing REMS prescriptions by up to 80%, and the validated prototype helped Huddl secure funding with the University of California San Francisco.

Figma Claude Code TestFlight

View case study → 2025 Mystique Productions

Growing Traffic Through a Full Website Rebuild

Designed, built, and launched a new marketing website for Mystique Productions, a Chicago corporate entertainment company whose old site looked dated, as the only designer and developer on the project. In about 2 months I explored more than 12 visual concepts, built a design system, cut a custom video for every service page, and launched on Squarespace with SEO and accessibility built in and a team trained to run it themselves. In the first 6 months after launch, traffic rose more than 40% over the old site's benchmarks, and contact-form requests rose about 20%.

Figma Photoshop Movavi Video Editor Squarespace HTML/CSS Google Search Console

View case study → 2025 EcoProducts

Enhancing eCommerce through Information Architecture

Rebuilt the online store's information architecture for EcoProducts, a compostable food service products company whose conversions dropped 10% after a product expansion forced a reorganization. As Senior UX Designer, I owned the information architecture and conversion flow: I watched user sessions, interviewed users, and ran open and closed card sorts, then rebuilt the structure around how customers look for products. We also showed shoppers that recommended lids and other items were compatible, and kept customers' own product names searchable. Three months after launch, conversions were up 12%, past EcoProducts' baseline.

Figma FigJam Hotjar BigCommerce

View case study → 2026 Kasasa

Unifying a Fragmented Sales Demo into One Cohesive Experience

Led design and project management on a sales demo for Kasasa, whose demo tools didn't talk to each other, so salespeople configured each one by hand and stuck to a tight script. Starting from the information architecture, I designed one demo that works whether a salesperson leads it or someone explores it on their own, lets viewers see every product as a new user or a power user, and carries data across the whole platform so a change in one product ripples through the rest. Testing with about 8 salespeople added the emails and other collateral users receive along the way. The demo rolled out to Kasasa's sales team to incredibly positive feedback, getting product and sales on the same page.

Figma Figma Make Claude Code

View case study → 2026 CS DISCO

Using AI to Transform the Legal Sector

Helped CS DISCO's product leadership pick its AI "big bet" in a week-long in-person workshop, at a time when its AI chatbot wasn't getting used and its board needed a plan for how DISCO would evolve and stand apart. As Senior Designer, I turned the team's ideas and rough sketches into 5 clickable, mid-fidelity prototypes in a day and a half, built in Claude Code from Figma designs, in time to put them in front of real users on the final day. The best of those concepts converged into one new platform concept. DISCO's Chief Product Officer took our handoff to the board and secured additional funding, and the concept is now in build for a 2027 release.

Figma Claude Code

View case study →

Let's talk.

Open to full-time and contract product design & strategy roles, remote or Chicago-based. Reach out any time.

Tyler Entingh · Chicago, IL tyler.entingh@gmail.com | LinkedIn