Founding Senior Software Engineer

Chestnut, backed by a16z, is applying modern solutions to transform a $7B industry. Our customizable, easy-to-use producer management and compensation platform is purpose-built to address the insurance industry’s unique challenges.

We help customers break free from legacy constraints, static compensation models, and manual processes—turning commissions into a dynamic revenue driver that unlocks growth.

We’re tackling one of the hardest problems in insurance. If you love solving complex challenges and want to work directly with a founding team building something groundbreaking, let’s chat!

Chestnut is, at its core, a technology company, and we are building the best team! We are looking for engineers who are excited to be part of our early story and who want to build a transformational company. We hire engineers who have a broad set of technical skills, are highly cross-functional, and are eager to solve a wide range of engineering challenges. Our ideal candidate has a strong sense of ownership and enjoys owning projects from inception to scaling it in production. We value people who take pride and ownership in their work and who show an aptitude for learning quickly. As an early employee, you will be working with a nimble team of committed and talented engineers and will have a large, long-term impact on technical design and engineering culture.

We are looking to expand our founding engineering team. Our team is inclusive, transparent, and takes large ownership in driving features from 0 to 1. We are looking for someone who is equally interested in developing robust APIs to stand the test of time as they are in developing innovative solutions to solving tough data modeling or UX challenges.

• Architect & Build – Design, develop, and deploy scalable software solutions from scratch

• Full-Stack Development – Own backend and frontend systems, ensuring seamless performance

• Technical Leadership – Drive engineering decisions, set best practices, and mentor as the team grows

• Rapid Iteration – Prototype, ship, and refine features based on user feedback

• Scalability & Performance – Ensure system reliability and efficiency as the platform scales

• Infrastructure & DevOps – Manage cloud infrastructure, CI/CD pipelines, and security best practices

• Cross-Functional Collaboration – Work closely with founders, product, and design to shape the roadmap

• 3+ years of experience as a backend and/or full-stack engineer

• Strong understanding of data structures, algorithms, and software design principles

• Expert-level knowledge of Golang programming language and ecosystem

• Familiarity with containerization and orchestration technologies like Docker and Kubernetes

• Experience working with Git and writing technical specs

• Experience working with gRPC and Protocol Buffers

• Bachelor’s and or Master’s degree in Computer Science or another STEM field (or equivalent work experience)

• An entrepreneurial spirit - you have or have always wanted to start a company

• Worked at an early stage (Seed or Series A) company, and/or a company that services the insurance industry

• Familiarity with TypeScript / React or similar frameworks

• Experience managing ETL data pipelines

• Experience with general ledgers and double entry accounting

• Experience with Terraform or other IaC equivalent technologies

• Competitive salary and equity, with 10 year exercise window for stock options

• Remote-first work culture

• Quarterly offsites for all of us to bond

• Unlimited PTO with 4 weeks recommended per year

• Top notch health, dental, and vision insurance subsidized by us