Senior Product Manager

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. This role is 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.

About the role

We're building an AI system that learns from how domain experts make decisions — and gets measurably better over time. The challenge isn't building another chatbot or copilot. It's designing a system that can extract structured intelligence from messy, real-world professional workflows, identify reliable patterns across many decisions, and surface that knowledge to the point where it's actually useful — without requiring anyone to change how they work.

You'll be the founding partner on the pod embedded in a team of AI and software engineers. This isn't a conventional PM role. You're the person who owns the seam between humans and the system, runs a parallel build track so the pod isn't single-threaded on engineering, and holds us accountable to whether the engine is actually learning.

You'll report to the Director of Product and interface regularly with the leadership team as the voice of the pod — communicating progress, surfacing blockers, and translating system performance into strategic implications.

What you'll do

• Sit alongside brokers. Watch them work. Try interaction patterns. Discover what "human in the loop" actually means in practice — not as a phrase, as a working interaction pattern.
• Ensure the team is solving the right problem. You are the interface between what brokers need and what the system can produce.
• Map workflows into tangible assets, advice units, a

[…]
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 .