Senior Software Engineer (Path to Tech Lead)

Chestnut (Headquarters: Remote)

Golang TypeScript React gRPC Protocol Buffers CI/CD Terraform Pulumi Docker Kubernetes AWS Infrastructure DevOps Backend Frontend Full Stack Insurtech Fintech Senior Tech Lead Full Stack Engineer Back End Engineer Staff Engineer

Company: 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. We are a well funded, close-knit seed stage insurtech building next-gen enterprise infrastructure.

About the Role:
We’re expanding our founding engineering team and looking for a senior engineer (4+ YoE) 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. 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

Ideal Candidate:
A passionate full stack Golang Developer with a track record of building high-quality applications who wants to be part of a vibrant team that embraces innovation. Someone looking to step into a tech lead position and build something enduring.

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

Benefits:
* Competitive salary and equity, with 10 year exercise window for stock options
* Remote-first work culture (West Coast preferred timezone overlap)
* Quarterly offsites
* Unlimited PTO with 4 weeks recommended per year
* Top notch health, dental, and vision insurance subsidized by us