Principal Engineer

Vouch is the insurance broker that powers ambition.

We’re a tech-enabled insurance advisory and brokerage purpose-built for growing companies in technology, life sciences, and professional services. Our clients are ambitious leaders building complex businesses, and we help them manage risk with tailored advice, smart coverage, and responsive service.

Backed by over $200M from world-class investors, Vouch combines deep industry expertise with AI-powered tools to deliver a better insurance experience. Our digital workflows reduce friction, speed up decisions, and give our clients the confidence to move faster.

Not only is this an exciting and growing team where you can drive a real impact on our operational scalability, but Vouch is also the preferred insurance provider to customers of Y Combinator, Brex, Carta, and WeWork. We’re a quickly growing startup that believes in transparency and acknowledgment with our team members and cultivating a values-driven company. Our values are  Be Client Obsessed ,  Own it together ,  Act with integrity and empathy ,  Stay Curious and Grow , and  Empower People .

Vouch has employees located across the U.S., with offices in San Francisco, Chicago, and New York City. This role will be aligned to our Chicago office. While this role has hybrid work flexibility, we require team members to be in the office at least three days per week (Tuesday, Wednesday and Thursday) to foster close collaboration and team building.

Vouch's engineering organization is becoming agent-native: a large and growing share of our production code is written by AI coding agents working inside human-governed guardrails. That moves the hard problems. Writing code got cheap; deciding what to build, keeping the architecture coherent, and proving that what shipped is correct did not. This role owns that layer.

This is a principal-level individual contributor seat reporting directly to the CTO, with a mandate that spans our estate: a harness for agent-built software — your first ownership deliverable — production AI doing judgment-heavy insurance work, a backend whose bounded contexts need to become real, and the cloud platform underneath all of it.

We are not going to lay the whole system out in a posting — we would rather keep the details as our edge until you are across the table from us. The short version: we extracted the machinery that let a small team ship roughly 1,100 governed changes in seven weeks at a sub-1% change-failure rate, and we are generalizing it into a platform – leaving open technical questions are the kind this role would actually want to be responsible for answering.

• Own the platform that governs agent-built software. A harness where markdown specifications compile to a traceability lock, deterministic gates decide “done,” every agent action leaves tamper-evident evidence, and a calibrated multi-vendor panel of LLM reviewers blocks what humans should not have to catch. You will take it from working extraction to adopted platform: scope its next milestone, build its plugin surface, operate and score the review seats, and prove it generalizes beyond the repository it was born in.
• Make bounded contexts real across our backend. Our backend estate asserts “one service = one bounded context”; a handful of services actually implement ports and adapters; the rest is your brownfield. You will turn design-doc DDD into enforced architecture — context maps, anti-corruption layers, boundary checks that run in CI — without freezing a team that ships daily.
• Ship agentic systems that do real insurance work. Durable multi-week agent workflows with human approval gates, tool contracts and capability boundaries, planner/executor orchestration — extended in production, in front of the experts whose judgment they encode.
• Make model behavior measurable — and autonomy earned. Eval suites as merge gates, golden datasets, LLM tracing and token/cost observability, calibration of LLM reviewers against ground truth. Autonomy expands when the evidence says so, and you own the…