VP of Engineering

Chestnut is building the first AI-native operating system for insurance distribution by transforming how the $1T+ insurance industry allocates its largest spend: sales and distribution.

Backed by a16z, we’re replacing legacy systems with a modern, flexible platform that helps carriers automate complex workflows, optimize every distribution dollar, and unlock new growth. We have major insurers under contract, and early adopters are expanding.

This is a generational platform shift. Recent advances in agentic AI make it possible to automate what was once manual and error-prone. We’ve spent years building the data model and context layer required to make this real, and now we’re scaling with urgency.

At Chestnut, we operate with the belief that small, high-context teams working with best-in-class tools and colleagues can achieve outsized results. We embody what it means to be AI-lean: chasing 10x productivity gains that allow us to scale impact beyond our headcount.

If you’re excited to modernize the infrastructure of one of America’s most essential industries, we’d love to meet you. Whether shaping core product experiences or laying the groundwork for intelligent automation, your work will accelerate a once-in-a-generation transformation.

Chestnut is a technology company at its core, building the infrastructure to power the future of AI in insurance. Realizing that vision requires both a modern, reliable foundation and the intelligence layer on top. Our engineers work across this stack, from designing data models that capture the nuance of insurance workflows, to developing APIs that support intelligent automation, to shipping user-facing product experiences and early AI copilots.

As VP of Engineering, you’ll scale and lead a team of exceptional engineers while building the systems, processes, and culture that make velocity and quality inevitable. You’ll partner closely with product, design, and founders to ensure we’re shipping impactful features fast, hiring best-of-the-best talent, and laying the foundation for long-term technical excellence.

• Accelerate product velocity: Shape lightweight rituals and engineering practices that shorten cycle times and improve delivery predictability.

• Own recruiting excellence: Build and refine a high-signal hiring funnel, surfacing the best-of-the-best technical talent through referrals, targeted outreach, and a world-class candidate experience.

• Lead with clarity: Align engineering priorities with company goals, ensuring we invest in both new features and technical foundations.

• Mentor and grow the team: Create a culture of strong ownership, continuous learning, and technical craftsmanship.

• Scale processes, not bureaucracy: Design systems and frameworks that improve speed without slowing down our builders.

• Drive technical alignment: Partner with product to ensure we’re shipping the right solutions, with clear architecture and reliable systems.

• 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.

• Engineering velocity has improved measurably, with tighter planning rhythms, clearer ownership, and <2-week average cycle times on core features.

• Top-of-funnel quality has increased, driven by referral-based outreach and a more structured, high-signal hiring process.

• A clean, scalable evaluation loop is in place making it easier for engineers to participate in hiring without burning time or context.

• Critical technical foundations are identified and prioritized, including key platform investments needed to support AI features and scale.

• Team health is trending up engineers are energized, empowered, and clear on what matters.

• 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