Description:

Chestnut is a company backed by a16z, focused on transforming the insurance industry with a customizable producer management and compensation platform.
The company aims to help customers overcome legacy constraints and static compensation models, turning commissions into a dynamic revenue driver.
The role is for a Senior Software Engineer who will help scale the founding engineering team and lay the groundwork for the platform.
Responsibilities include defining core system architecture, leading infrastructure efforts, and ensuring product resilience as the company moves to production scale.
The position is ideal for a seasoned individual contributor ready to take ownership and grow into a tech lead role.
Key tasks include designing production-grade systems, owning infrastructure setup and automation, contributing across the stack, ensuring production readiness, driving technical leadership, and collaborating with cross-functional teams.

Requirements:

Candidates should have 4–6+ years of professional experience, preferably with early-stage teams.
Strong experience in architecting and maintaining production systems is required.
Proficiency in Golang and a deep understanding of modern backend design patterns are essential.
Experience with gRPC/Protocol Buffers, CI/CD, and cloud-native architecture is necessary.
Comfort with Terraform/Pulumi, Docker, Kubernetes, and cloud services (preferably AWS) is expected.
Candidates should possess strong judgment regarding abstraction, tradeoffs, and performance.
Clear communication skills and the ability to thrive in fast-moving, collaborative environments are important.
A builder’s mindset, with eagerness to own outcomes and take initiative, is desired.

The position offers a competitive salary and equity, with a 10-year exercise window for stock options.
The company promotes a remote-first work culture.
Employees can participate in quarterly offsites to foster team bonding.
Unlimited PTO is provided, with a recommendation of 4 weeks per year.
Top-notch health, dental, and vision insurance is subsidized by the company.