VP of Engineering

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July 29

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Chestnut

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Insurance • SaaS

Chestnut is a company that provides a modern distribution management platform tailored specifically for the insurance industry. Their solution, Chestnut PPM, focuses on transforming producer management and incentive compensation into strategic revenue drivers for insurance carriers. The platform offers features like producer performance management, hierarchy management, and debt management, along with comprehensive compliance tracking and performance insights. Chestnut's architecture is designed to provide high-volume processing, secure scalability, and actionable insights to enhance engagement, growth, and retention. Built with the insurance sector in mind, it supports the complexities of compliance, commissions, and incentive structures unique to the industry.

11 - 50 employees

☁️ SaaS

📋 Description

• Chestnut is building the first AI-native operating system for insurance distribution. • We’re replacing legacy systems with a modern, flexible platform that helps carriers automate complex workflows. • This is a generational platform shift. • Recent advances in agentic AI make it possible to automate what was once manual and error-prone. • At Chestnut, we operate with the belief that small, high-context teams can achieve outsized results. • If you’re excited to modernize the infrastructure of one of America’s most essential industries, we’d love to meet you. • 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.

🎯 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