Job description
About Chestnut
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!
About the Role
We’re expanding our founding engineering team and looking for a senior engineer with strong architectural instincts, production experience, and infrastructure mindset to help us scale. This isn’t just another dev job — it’s a chance to lay the groundwork for the platform and team that will power the future of insurance distribution.
You’ll help define core system architecture, lead foundational infrastructure efforts (especially around infrastructure as code, CI/CD, and observability), and play a key role in keeping our product resilient as we move from 0 → 1 to production scale. We’re looking for someone who can balance fast iteration with long-term maintainability and understands that great infrastructure is product work.
This role is ideal for a seasoned IC who’s ready to take ownership, lead initiatives, and grow into a tech lead role.
What You’ll Do
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.
What We’re Looking For
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
Bonus Points
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
This is a high-ownership role with real leadership upside. If you’ve been looking to step into a tech lead position and build something enduring — this is it.
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
