Chestnut is hiring a VP of Engineering to scale and lead a team of exceptional engineers. You will build the systems, processes, and culture that make velocity and quality inevitable. You will partner closely with product, design, and founders to ensure impactful feature delivery and lay the foundation for long-term technical excellence.
What You'll Do
- Accelerate product velocity by shaping lightweight rituals and engineering practices that shorten cycle times and improve delivery predictability.
- Own recruiting excellence by building and refining a high-signal hiring funnel through referrals, targeted outreach, and a world-class candidate experience.
- Lead with clarity by aligning engineering priorities with company goals, ensuring investment in both new features and technical foundations.
- Mentor and grow the team by creating a culture of strong ownership, continuous learning, and technical craftsmanship.
- Scale processes, not bureaucracy, by designing systems and frameworks that improve speed without slowing down builders.
- Drive technical alignment by partnering with product to ensure shipping the right solutions with clear architecture and reliable systems.
What We're Looking For
- You have scaled and led engineering teams at a fast-paced startup or high-growth company.
- You care deeply about velocity and quality and know how to achieve both.
- You have a track record of hiring exceptional engineers and shaping a high-performance culture.
- You thrive in ambiguity, value autonomy, and enjoy building structure where it doesn’t yet exist.
- You are curious, pragmatic, and energized by learning complex domains like insurance and agentic AI.
- You are comfortable being hands-on when necessary while setting up your team for independent success.
Benefits & Compensation
- Competitive salary and equity, with a 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
Work Mode
This role operates in a remote-first culture.
Chestnut operates 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.
