VP of Engineering
ChestnutUnited States
Posted July 29, 2025
Full Time
About the Company
Chestnut is redefining distribution infrastructure for insurance carriers. Our platform, Producer Performance Management (PPM), features a modular, API-first architecture that powers onboarding, producer management, and incentive compensation. We combine insurance-native data structures (transactions, policies, hierarchies) with an extensible logic engine. That means carriers can support non-standard hierarchies, ingest external data, adapt bonus rules across regions, and much more—without months of custom work. The result: ✅ Faster implementation and time to value ✅ Full control over business logic and compensation strategy ✅ A system that evolves with your distribution model Chestnut is an Andreessen Horowitz portfolio company and built by a team with deep experience in enterprise SaaS and insurance. We’re trusted by carriers who need infrastructure that performs—and adapts—as they grow.
Job Description
Chestnut is building an AI-native operating system for insurance distribution, and we're looking for a VP of Engineering to lead our engineering team and build the systems and processes that make velocity and quality inevitable.
Requirements
- Have scaled and led engineering teams at a fast-paced startup or high-growth company.
- Care deeply about velocity and quality — and know how to achieve both.
- Have a track record of hiring exceptional engineers and shaping a high-performance culture.
- Thrive in ambiguity, value autonomy, and enjoy building structure where it doesn’t yet exist.
- Are curious, pragmatic, and energized by learning complex domains like insurance and agentic AI.
- Are comfortable being hands-on when necessary while setting up your team for independent success.
Benefits
- Competitive salary and equity, with 10 year exercise window for stock options
- Remote-first culture built on trust, autonomy, and high performance
- Team offsites for all of us to bond
- Take what you need vacation policy
- Top notch health, dental, and vision insurance subsidized by us
