Principal Engineer

About Vouch:

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.

Why should you join our team and Vouch?

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."

What does a work environment look like at Vouch?

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.

Why This Role Matters:

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.

What You'll Do:

• 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 evidence.
• Run platform and delivery engineering at organization scale. An AWS multi-account estate in Terraform behind GitOps; two orchestrators in production; CI/CD pipelines that are generated, not hand-written; ephemeral environments per pull request. You will make the paved road faster than the shortcut.
• Be the CTO's architecture thought partner - and raise the bar. Strategic-design working sessions, ADRs with teeth, review comments that catch what tests cannot; specifications written to be read by humans and coding agents alike, mutation-testing bars, adversarial review. When we argue about where a boundary belongs, you are the other half of the argument.

About You:

A principal engineer here is equal parts AI engineer, DevOps engineer, and software architect. We mean that literally, and we will interview for all three.

You are a software architect.

• You have shipped domain-driven design, not just read about it: a bounded-context map you drew and then enforced, an anti-corruption layer that saved a migration, a hexagonal refactor that survived contact with a deadline - and you know when the pattern is overkill.
• You are at home in more than one language ecosystem - e.g., systems-level work in Rust or a peer language, large-scale strictly-typed TypeScript, etc. - and you know which discipline each one demands.

You are an AI engineer.

• You have built and operated agent systems in front of real users - tool contracts, capability boundaries, approval gates - and the machinery that makes them trustworthy: eval gates, provenance capture, autonomy expanded through earned evidence rather than optimism.
• Frontier models are daily instruments in how you build, and "the model can probably do this" is a hypothesis you test with an eval, not a hope you ship on.

You are a DevOps engineer.

• You have run infrastructure other people depend on: infrastructure-as-code at organization scale, GitOps, container orchestration, secrets, observability-as-code - and a pager you did not hand back.
• You treat delivery machinery - CI/CD, environments, releases - as a product with users, and you can argue a migration in cost and risk rather than tool preference.

Across all three.

• You reason in writing. ADRs, design docs, review comments - decisions here live in documents, and you make arguments better by writing them down.
• You multiply rather than add. The measure of this seat is what the engineers and agents around you can safely do a quarter after you arrive.
• You have experience in and passion for early-stage startups and/or high-growth environments

Nice To Have:

• Typescript, Python, and/or Rust in production
• A shipped record of brownfield modernization - strangler migrations, context extraction, boundary enforcement in CI
• Durable-execution engines and event-driven systems with schema governance
• Eval frameworks, LLM observability, and MCP
• A background in insurance or other regulated categories

Vouch provides several benefits to help you bring your best self to work:

• Competitive compensation and equity packages
• Health, dental, and vision insurance
• Parental leave
• Flexible vacation time
• Wellness allowance
• Technology allowance
• Company-sponsored personal and professional development
• L&D: Partnerships with Ethena and monthly Lunch & Learns
• Wellbeing: access to many wellbeing perks, including Peloton, Fetch, OneMedical, Headspace care+, etc.
• Caregiver Support: company seed into the dependent care FSA and company sponsored Care.com membership.
• Regular performance reviews: Vouch conducts regular performance discussions with all team members, offering goal setting and check-ins, development discussions, and promotion opportunities.

What to expect in a typical interview process:

(Please note these steps may vary slightly depending on the role)

• 30-minute phone call with our recruiting team
• 30-45 minute video interview with the hiring manager
• Case study/technical screen
• Meet the team! 30-45 min 1:1 video discussion with 3-4 team members you'd work closely with in the role
• Executive chat

Compensation philosophy:

Our salary ranges are based on paying competitively for our size and industry and are part of our total compensation package, which also includes benefits and other perks. We also include stock options in all compensation packages and believe all Vouch employees should have the opportunity to become owners in the company. Individual pay decisions are based on a number of factors, including qualifications for the role, experience level, skill set, location, and business need. The pay range provided is subject to change and may be modified in the future.

Vouch believes in putting our people first, and building a diverse team is at the front of everything we do. We welcome people from different backgrounds, experiences, perspectives, and ranges of abilities. We are an equal-opportunity employer and celebrate the diversity of our growing team.


If you require reasonable accommodation to complete this application, interview, complete any pre-employment testing, or otherwise participate in the employee selection process, please direct your inquiries to View email address on click.appcast.io.

The pay range for this role is:

245,000 - 285,000 USD per year (Chicago, IL (Hybrid))