Senior Product Designer · Chicago, IL

Design-minded.
Delivery focused.

Hands-on design and delivery, from strategy to shipped product.

01
Who I am

About

10+ years leading end-to-end product design across SaaS, enterprise, and startup environments. Most recently specializing in designing and building AI-powered products — for internal operations and enterprise clients alike — using modern AI-assisted development tools to move from concept to shipped software. Skilled at translating user research and business objectives into accessible, high-impact design solutions, and at leading cross-functional teams through the full product lifecycle with agile practices.

01 / 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.

02 / 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.

03 / Accessible by default

Treats WCAG as a baseline, not a checkbox.

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

04 / Strategic operator

Comfortable from wireframe to client pipeline.

Reads a market and a Figma file with the same fluency.

AI Product Design & Strategy Claude Code Vercel Railway GitHub Cursor Figma Adobe Creative Cloud HTML / CSS / JavaScript Prompt Engineering User-Centered Design Wireframing & Prototyping User Research Design Systems Agile / Scrum WCAG Accessibility
02
Career

Experience

Full detail lives in the résumé — this is the shape of it.

Aug 2024 — Present
Chicago, IL (Remote)
Senior Designer & Project Manager
SeeSaw Labs

Client-facing design and delivery lead for AI-powered products, from kickoff through launch. Owns project management across cross-functional teams and ships features directly using Claude Code, Vercel, Railway, and GitHub — while mentoring design and product teams on integrating generative AI into their workflows.

Oct 2024 — Jul 2026
Chicago, IL (Remote)
UX Strategist, New Projects (Contract)
Slide UX

Led the sales process for new client engagements — discovery calls through proposal, contract, and kickoff — then designed and delivered the UX/UI work itself, building relationships with prospective clients and partners along the way.

Apr 2019 — Apr 2024
Chicago, IL (Remote)
Senior Product Design Instructor
Flatiron School LLC

Promoted from UX/UI Design Instructor (2019) to Senior Product Design Instructor (2021). Designed and taught product design and front-end curricula for entry-level students and enterprise clients, ran daily scrum rituals, and ensured all training content and student work met WCAG accessibility standards.

Oct 2020 — Apr 2021
Austin, TX (Remote)
Product Design Program Lead (Contract)
U.S. Army Software Factory

Created and delivered a customized product design training program for active-duty soldiers in HTML/CSS, Figma, and entry-level product design, adhering to U.S. Department of Defense technical constraints.

Jul 2017 — Apr 2019
Chicago, IL
UX/UI Designer
Strata Decision Technology

Designed SaaS solutions across a platform used to create, implement, and track big-data initiatives for major healthcare systems. Identified and owned internal design initiatives, including a brand refresh and design system rollout, backed by qualitative and quantitative user research.

03
Selected work

Case studies

Placeholder cards below — swap in 2-4 real case studies (problem, your role, outcome, a screenshot or link).

Case study title

One or two sentences on the problem, your role, and the outcome.

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Case study title

One or two sentences on the problem, your role, and the outcome.

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Case study title

One or two sentences on the problem, your role, and the outcome.

Add project

Case study title

One or two sentences on the problem, your role, and the outcome.

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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