Senior Product Designer · Chicago, IL

Design-minded.
Delivery focused.

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

01
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. Lately, I've been deep in AI-powered products, for internal teams and enterprise clients alike, using modern AI-assisted development tools to take ideas from a napkin sketch to shipped software fast. I know how to turn user research and business goals into design that's genuinely accessible and high-impact, and I know how to lead a cross-functional team through the whole product lifecycle without losing momentum. Below are some skills I like to highlight for folks I work with:

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.

02
Career

Experience

Aug 2024 — Present
Chicago, IL (Remote)

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)

Led the sales process for new client engagements, from 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)

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)

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

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
Case studies

Featured Work

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