VP of Engineering - Remote

Overview

The VP of Engineering at Chestnut will lead and scale a team of exceptional engineers while building systems, processes, and a culture that drives velocity and quality in delivering AI-native solutions for the insurance industry.

In Short

• Accelerate product velocity through improved engineering practices.
• Own recruiting excellence to build a high-signal hiring funnel.
• Align engineering priorities with company goals.
• Mentor and grow the engineering team.
• Design systems that enhance speed without bureaucracy.
• Drive technical alignment with product teams.

Requirements

• Experience in scaling and leading engineering teams at fast-paced companies.
• Strong focus on achieving velocity and quality.
• Proven track record of hiring exceptional engineers.
• Ability to thrive in ambiguity and create structure.
• Curiosity and pragmatism in complex domains like insurance and AI.
• Hands-on approach when necessary.

Benefits

• Competitive salary and equity with a long exercise window for stock options.
• Remote-first culture based on trust and autonomy.
• Team offsites for bonding.
• Flexible vacation policy.
• Comprehensive health, dental, and vision insurance.