Senior Software Engineer

Summary

Join Chestnut, a company backed by a16z, revolutionizing the $7B insurance industry with its innovative platform. We are seeking a senior engineer to join our growing founding engineering team. This role offers the opportunity to build the foundation of our platform and team, shaping the future of insurance distribution. You will define core system architecture, lead infrastructure efforts (including infrastructure as code, CI/CD, and observability), and ensure product resilience. This is a high-ownership role with significant leadership potential, ideal for a seasoned individual contributor ready to take ownership and grow into a tech lead position. We are looking for someone who can balance fast iteration with long-term maintainability and understands that great infrastructure is product work. The role involves architecting for scale, implementing infrastructure as code and DevOps, contributing across the stack, ensuring production readiness, providing technical leadership, and partnering cross-functionally.

Requirements

• 4–6+ years of professional experience, ideally with time spent on early-stage teams
• Strong experience architecting and maintaining production systems
• Proficiency with Golang and deep understanding of modern backend design patterns
• Experience with gRPC/Protocol Buffers , CI/CD , and cloud-native architecture
• Comfort working with Terraform /Pulumi, Docker, Kubernetes, and cloud services (AWS preferred)
• Strong judgment around abstraction, tradeoffs, and performance
• Clear communicator who thrives in fast-moving, collaborative environments
• A builder’s mindset — eager to own outcomes and take initiative

Responsibilities

• Architect for Scale: Design clean, extensible, and production-grade systems with a bias toward simplicity and performance. You’ll lead foundational technical decisions as we scale up
• Infrastructure as Code & DevOps: Own infrastructure setup and automation. Implement and maintain Terraform (or equivalent), CI/CD pipelines, secrets management, monitoring, and alerting. Ensure we can deploy with confidence
• End-to-End Ownership: Contribute across the stack (Golang backend, TypeScript/React frontend), with an eye toward reliability, performance, and clarity
• Production Readiness: Ensure our systems are testable, observable, and resilient. Help define and enforce the practices that keep us up and running as we onboard real customers
• Technical Leadership: Drive technical planning, design reviews, and long-term thinking. Help us scale the engineering function by mentoring future hires and setting a high bar for quality
• Cross-Functional Partnership: Work closely with the founders, product, and design to shape the roadmap and prioritize high-impact work

Preferred Qualifications

• Experience in highly regulated domains (e.g., insurance, fintech, healthcare)
• Background in ETL pipelines, event-driven architecture, or double-entry accounting systems
• Familiarity with frontend frameworks like TypeScript/React
• Exposure to multi-tenant or enterprise-grade SaaS environments

Benefits

• 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