1 year ago
Seattle, WA, USA or San Francisco, CA, USAStaff+
Responsibilities
- Lead the design and implementation of critical systems that serve as platform building blocks.
- Make architectural decisions focused on scale, performance, and maintainability.
- Partner with product, design, and engineering leaders to define roadmaps and technical investments.
- Identify and unblock high-risk areas across teams, contributing hands-on when needed.
- Improve engineering quality through mentorship, role modeling, and code review.
- Help establish engineering culture, norms, and hiring standards.
Requirements
- At least 8 years of experience building and scaling complex software systems.
- Experience leading architecture or technical strategy for a product or platform team.
- Comfort working across backend, data, and infrastructure layers, with the ability to contribute to frontend work when needed.
- Strong systems thinking and pragmatic problem-solving skills.
- Interest in shaping the technical direction of a growing company.
- Strong communication skills and ability to work across disciplines.
- Comfort with ambiguity, real-world data, and building for scale.
Benefits
- Remote-first work arrangement
- Competitive salary and equity with a 10-year stock-option exercise window
- Team offsites
- Flexible take-what-you-need vacation policy
- Subsidized health, dental, and vision insurance
Tech Stack
About Chestnut
Chestnut builds cloud-based software for insurance carriers and distribution partners to manage producers, commissions, and agent engagement. Its platform centralizes producer management and compensation workflows and includes a mobile app for agents, aiming to turn commissions into a controllable revenue lever. Chestnut is privately held and has raised a seed round from investors including Andreessen Horowitz, Liquid 2 Ventures, and Detroit Venture Partners.