Senior Member of Technical Staff, Developer Experience

The Problem 36 million businesses in America need insurance. 77% are underinsured. 40% have no coverage at all. We're building 90%+ AI-led commercial insurance distribution. ~1,000 new customers/month, 100x growth in a year, scaling toward Series B. Our engineers and our coding agents both 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. Engineers ship at the speed of the slowest part of the inner loop. Make the inner loop fast and trustworthy. The Thesis The fastest teams are not fast because they tolerate chaos. They are fast because the path from idea to production is short, trusted, and boring in the best way. At Harper, that path has to work for humans and coding agents. You will build the loop engineers live inside every day: dev environments that boot, tests people trust, CI that gives signal, PR preflight that catches risk, and tooling that makes the right pattern easier than the wrong one. The Role Harper operates like a factory with a series of modules spanning the full lifecycle from intake through renewals. Across them we run a stack of internal AI systems covering operator guidance, the operational backbone that matches risks to underwriters, autonomous communications, and voice AI for customer interactions. You'll work alongside the engineer setting the developer-experience direction to keep the inner-loop + outer-loop stack fast and reliable for every product engineer at Harper. What You'll DoCut CI build times - Monorepo tuning, incremental builds, remote caching. Target: CI - Local/staging/CI parity. Boot a working env in - 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 monitoringShip PR preflight automation - The robot summary every PR opens with: services touched, tests run, missing tests, migrations, critical-path warningsBuild internal developer-platform pieces - Service templates, scaffold generators, doc indexers, internal CLI commands You Might Be a Fit If...You've shipped developer tooling / CI / build infra that other engineers actually adopted at a high-growth companyYou can name a CI time you cut and the technique you usedYou've worked with at least one monorepo build system at depthYou've integrated an eval framework into a real CI pipelineYou write code with AI daily and have opinions on rules files, repo-level agent guidanceYou're 3-6 years into your career Requirements3-6 years software engineering experienceDeveloper platform / CI/CD / build infra / dev-environment experienceProduction eval-framework integration into CI (at least one)Strong written communicationBased in San Francisco or willing to relocate Nice to HaveBuilt devcontainers or comparable cloud dev environmentsCustom lint-rule authoringOpen-source contribution to a developer-tools project CompensationOTE: $176,000-$253,000 cash compensation (base salary + target performance bonus)Equity: competitive equity, so you share in the company you are helping buildLocation: San Francisco, in-office BenefitsHealth, dental, and vision insuranceCommuter benefitsTeam meals and snacks The ProcessFounder call (15 min) - Mission, pace, scopeTech Lead deep-dive (60 min) - Inner-loop / CI conversationSuper Day on-site - full-day simulation of working at Harper: dev-environment debug, CI design, code review, team context, and founder/CTO timeFounder + Tech Lead offer conversation - 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.