StaffEngineer,EngineeringProductivity&AIQuality

STAFF ENGINEER, ENGINEERING PRODUCTIVITY & AI QUALITY Harper is an AI-native commercial insurance company, based in San Francisco and built from scratch. Most knowledge work is judgment locked inside people's heads — the exceptions, the precedents, the decision traces no one ever wrote down. Converting that judgment into software is one of the largest human-to-computational transitions still in front of us, and we think the most honest place to prove it is the hardest one: commercial insurance, a trillion-dollar industry that is still, even now, more than 90% done by hand. We're not patching legacy workflows or adding a copilot to them. We're rebuilding the business so that AI does the work and people do the judgment that AI can't yet — and then teaching it that, too. It's working: ~1,000 new customers a month and roughly 100x growth in the past year. That pace sets the culture. We're on-site in San Francisco, in the building together, working long days to high standards — because a rebuild this large doesn't happen part-time or by committee. Almost no one joins Harper because they're passionate about insurance. They join because they want to be on the frontier of the AI transition, doing the most consequential work of their career, in a company being built to define a category rather than join one. If that's the work you're looking for, insurance is just where you get to do it. THE ROLE Every great AI company ends up building the same invisible machine: the harnesses, tests, instructions, and review loops that let a small team ship with impossible leverage. At Harper that machine is existential. Our agents write code, serve customers, assemble submissions, and make decisions that move revenue — and AI-generated code volume has pulled the scaling problem forward. Even with a 20-person engineering team, our coding agents create the surface area, review burden, and architectural drift of a 100-person org. If the rails are strong, twenty engineers operate like a hundre