VP of Engineering

Summary

Join Chestnut, a leading AI-native operating system for insurance distribution, as their VP of Engineering. You will scale and lead a team of exceptional engineers, building systems, processes, and a culture that prioritizes velocity and quality. Accelerate product velocity by shaping engineering practices, own recruiting excellence by building a high-signal hiring funnel, and lead with clarity by aligning engineering priorities with company goals. Mentor and grow the team, scale processes, and drive technical alignment with product teams. This is a unique opportunity to modernize the infrastructure of a vital industry and contribute to a generational platform shift.

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

Responsibilities

• 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’re investing 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

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