AI Engineer

The posting, as Vouch wrote it

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. 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.

The Role

Vouch is building AI software for judgment-heavy insurance work: a system that learns from experts and gets measurably better week over week. We are early — a small team, real experts, real production usage, real customers, and a lot of unanswered technical questions.

This is genuinely interesting work, and we say that well-aware of how every job posting claims that. We are betting on a specific approach to AI in a regulated domain, and we are not going to lay it all out in this posting — we'd rather it stay our edge until you're across the table from us. The hard problems live exactly where you'd hope — making an LLM system durable, auditable, and measurably improving, in a domain where being wrong has consequences.

You would join early in the system's life, in a rapidly evolving codebase that already carries more test code than source code. That ratio is not an accident; it is our style.

How we work, concretely: reasoning is written down and public — design docs land as pull requests, root-cause writeups happen in the channel, and demos are async videos every Friday morning. We ship to staging many times a day and to production behind consent-based pushes; standups are short and bot-recapped, and the real arguments happen in threads and design-doc reviews.

What You'll Do

• Ship agentic workflows end to end. Design tool contracts, capability boundaries, and approval gates for an agent doing real insurance work under human jud

[…]
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 recruiting@vouch.us .