Jake
Fleming
Summary
- Fifteen years of product design. Five and a half of them at Labelbox, where I went from lead designer to VP of Design and built the team along the way.
- I have managed designers and I have been the only designer in the building. Either way I stay close to the work.
- I ran a product design program for four years. Giving designers feedback that makes them better, fast, is a thing I have done a few hundred times.
- I can write production code (HTML, CSS, TypeScript, Swift), but these days I mostly don't have to. I build with frontier models: I decide what gets made and how it should work, then get into the details myself, the interaction, the copy, the edge cases, the code review, until it's right. Hellbox and blinkdiff were built that way.
- I sell software I made, so I know the whole funnel from the inside: how people find a thing, try it, decide, pay, and come back. I built the dashboard that tells me which trials will convert.
- I use data and experiments to decide what to work on and whether it worked.
Where I've worked
First designer at a health and longevity startup. I own product design end to end, from the invitation and onboarding flow a new client lands in, through the app they use every day, to the workspace their advisor works in. Built the design system that keeps a tiny team consistent across all three. Set up feature flags and experiments (GrowthBook) early.
Cortex is an engineering intelligence platform: a catalog of every service a company runs, scorecards for how healthy they are, and the dashboards engineering leaders use to decide what to fix. I was the principal designer, working on how engineering teams adopt it and keep using it.
Joined as the lead designer, ended up VP, stayed hands-on the whole time. Labelbox is a data labeling and model evaluation platform, a complicated product that a lot of people had to learn quickly, so much of the work was making it approachable: onboarding, first-project setup, the free tier, the paths from trying it to buying it, and the workflows that keep teams in it every day. I hired and ran the design team, set the bar for craft, built the design system, and did the reviews, while the whole AI field took off around us.
Designed the fraud-detection tools for Metromile Enterprise: an ML model flags a claim, an investigator decides if it's real. My job was the screen in between.
Ran the product design program for four years. Wrote the curriculum, taught it, critiqued a lot of work, and placed the people who came through it at startups.
Things I built
Sold directly. I designed the product, the site, the 14-day trial, the pricing, and the launch. Glyphs put it on their homepage. The dashboard I built for it tracks the funnel from download to trial to purchase and gives each live trial odds of converting, based on how the last hundred behaved.
Screenshot diffs on every pull request. A CLI, a GitHub Action, and a bot you tell "approve" when the change was on purpose. Built, priced, and launched in a week with frontier models doing most of the typing.
A prompt generator that has grown on its own for years because people keep sending it to each other.
Boxout and Goiters (typefaces), Cat Lady (a dungeon crawler on Steam), and a type design workshop I ran and wrote up.