Senior Member of Technical Staff, Developer Experience

Harper is an AI-native commercial insurance company in San Francisco. We're not bolting AI onto insurance — we're rebuilding the entire business as software, on a simple bet: turning expert human judgment into compute is one of the largest transitions left to make, and a trillion-dollar industry still run 90% by hand is the place to prove it. We've grown ~100x in the last year and we move at that speed — on-site, in person, long days, very high standards. Almost no one joins Harper for insurance; they join to build the company that replaces how it works.

The role

Engineers ship at the speed of the slowest part of the inner loop — and at Harper that loop has to run fast for humans and for coding agents, both of which now ship 5–10x faster than they did a year ago. Without rails (fast builds, reliable dev environments, merge queues, eval frameworks that catch regressions), that velocity quietly converts into rework, hotfixes, and weekend pages. The fastest teams aren't fast because they tolerate chaos; they're fast because the path from idea to production is short, trusted, and boring in the best way. That path is what you own. It's a direct lever on the bet: the faster and more trustworthy the loop, the more judgment-into-compute work the whole org ships per week. You'll work alongside the engineer setting developer-experience direction to keep the inner- and outer-loop stack fast and reliable for every product engineer at Harper.

What you'll do

• Cut CI build times. Monorepo tuning, incremental builds, remote caching. Target: CI under 5 min at p95.

• Own dev-environment reliability. Local/staging/CI parity, a working env booting in under 10 min, reproducible and containerized.

• Quarantine flaky tests. Detection, isolation, dashboard. Flaky tests get fixed or quarantined — never silently retried.

• Wire the eval stack into CI. Pre-merge gates, offline experiments, production trace monitoring.

• Ship PR preflight automation. The robot summary every PR opens with: services touched, tests run, missing tests, migrations, critical-path warnings.

• Build the internal developer platform. Service templates, scaffold generators, doc indexers, internal CLI commands.

What we're looking for

• 3–6 years building software, with developer-platform / CI-CD / build-infra / dev-environment experience that other engineers actually adopted at a high-growth company.

• You can name a CI time you cut and the technique you used, and you've worked with at least one monorepo build system at depth.

• You've integrated an eval framework into a real CI pipeline (at least one).

• You write code with AI daily and have opinions on rules files and repo-level agent guidance.

• Strong written communication.

• Bonus: devcontainers or comparable cloud dev environments; custom lint-rule authoring; open-source developer-tools contributions.

The reality

On-site in San Francisco, in person, long days, high standards. DX here is high-leverage and highly visible — when the loop is fast, twenty engineers and a fleet of coding agents move like a much larger org; when it's slow, everyone feels it. You'll build for an audience that notices immediately. The right person wants that pace and that scrutiny.

Logistics

• Compensation (OTE): $176,000–$253,000 cash (base + target performance bonus), plus competitive equity.

• Location: San Francisco, in-office. Based here or willing to relocate.

• Benefits: Uber commuter benefits; breakfast, lunch, and dinner provided; snacks and coffee stocked; free gym membership; health, dental, and vision.

• Process: Founder call (15 min) → Tech Lead deep-dive (60 min, inner-loop / CI) → Super Day on-site → founder + Tech Lead offer. No committee. Best offer, first.

To apply: If you've cut a 20-minute CI to 4, or boot times from 45 minutes to 6, or shipped an eval suite engineers actually trust — send your resume, the numbers, and the playbook.