5-8 years of experience in building and scaling production systems
Adaptability to thrive in early-stage environments
Proficient in writing clean, maintainable code
Ability to think in systems and design for flexibility and resilience
Demonstrated ownership and urgency in tasks
Passionate about real-world complexity, data modeling, and automation
Desire to help define future engineering practices at Chestnut
Responsibilities
Lead design and development of core systems including Go microservices and event-driven workflows
Collaborate with cross-functional teams to deliver high-impact features
Own architecture and implementation decisions for scalability and reliability
Contribute to core infrastructure such as observability and developer experience
Set technical excellence standards through mentorship and process improvement
Benefits
Competitive salary and equity with a 10-year exercise window for stock options
Remote-first culture emphasizing trust, autonomy, and performance
Team offsites designed to foster bonding and collaboration
Flexible vacation policy allowing employees to take what they need
Comprehensive health, dental, and vision insurance, largely subsidized by the company
Full Job Description
Engineering at Chestnut
We're building the modern infrastructure for AI-driven insurance operations. That means well-structured data models, real-time event pipelines, clean APIs, and usable tools that support humans and agents working in parallel.
As a Software Engineer at Chestnut, you'll join a high-agency, cross-functional team focused on delivering impactful features fast. You'll work across the stack, contribute to system design, and help shape the technical culture as we grow.
What You'll Do
Lead the design and development of core systems - from Go microservices and event-driven workflows to React UIs and automation layers
Partner cross-functionally to scope, prioritize, and deliver high-impact features that drive real business outcomes
Own architecture and implementation decisions end-to-end, ensuring long-term scalability and reliability
Contribute to and evolve core infrastructure, including observability, permissions, and developer experience
Set the bar for technical excellence - mentoring teammates, improving processes, and helping us scale with confidence
You Might Be a Fit If You...
Have 5+ years of experience building and scaling production systems
Thrive in early-stage environments and enjoy wearing many hats
Write clean, maintainable code and care about craftsmanship
Think in systems and design with an eye toward flexibility and resilience
Take ownership, act with urgency, and bias toward progress over perfection
Are energized by real-world complexity, data modeling, and automation
Want to help define the future of engineering at Chestnut
Our Stack
Languages: Go, TypeScript
Frontend: React, Tailwind
Infra: K8s, ArgoCD, Kargo, Temporal, Dagster
Data: Postgres, Dynamo, Snowflake
Benefits
Competitive salary and equity, with 10 year exercise window for stock options
Remote-first culture built on trust, autonomy, and high performance
Team offsites for all of us to bond
Take what you need vacation policy
Top notch health, dental, and vision insurance subsidized by us
