A few things about me.

Jesse Trippe

Lead product designer

I’m a lead product designer at Cityblock Health, working on the tools nurses and community health partners use to care for Medicaid and Medicare members. Before healthcare, I designed software for logistics and financial services.

I grew up in a small town in Michigan and moved to Chicago, where I found myself stuffing envelopes and foaming lattes. I went on to study visual communication at the School of the Art Institute of Chicago, taught myself HTML and CSS, and fell in love with building websites.

How I work

I start with the people doing the work: their responsibilities, rules, handoffs, and the workarounds they’ve built. Research helps me shape product direction and find steps the software can stop asking people to do. I keep checking after launch, using conversations and usage data to decide what to simplify or retire.

I move between product direction and implementation. I use prototypes to work through decisions with engineering and contribute production fixes when that helps the team move forward. In AI-assisted workflows, I make sources visible so people can check a recommendation before acting.

I help teams build on each other’s work through shared design systems, design studios, and mentoring. That includes connecting reusable patterns to code, reviewing work with designers, and helping them find projects aligned with their goals.

Experience

Selected experience

  • Cityblock Health 2023–present Lead product designer
  • Carta 2021–2023 Senior product designer
  • Amazon 2016–2021 Senior UX designer
  • Coyote Logistics 2011–2016 Senior product designer
  • Obama Reelection Campaign 2011 Front-end developer
Download resume (PDF) ↓

Contact

Let’s talk about your team and the work ahead.

jesset@me.com