Software Engineer (Mid-Level)
- Location
- San Francisco, CA (Remote)
- Listed
- Today
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
- Build the backbone of our AI-native platform - from Go services and event-driven workflows to React UIs and automation layers
- Work closely with product and design to ship fast, learn quickly, and iterate on high-impact features
- Own your work end-to-end - from architecture to deployment, with clear handoffs and strong accountability
- Scale our foundation - shaping infrastructure like observability, permissions, and dev tooling
- Move like a builder: stay unblocked, act with urgency, and focus on what matters most
You Might Be a Fit If You
- Have 3+ years building and scaling production systems with Go, TypeScript, and React
- Strong CS fundamentals - you design thoughtfully and build systems that last
- Have hands-on experience with gRPC, event-driven architecture, and clean, versioned APIs
- Are fluent in containers and modern orchestration tools like Temporal, Dagster, and ArgoCD
- Thrive in fast-paced, high-agency environments and know how to navigate tradeoffs
- Are curious about AI, drawn to complexity, and motivated to shape foundational systems in a massive industry
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
About Chestnut
Chestnut is building the AI-native operating system for insurance distribution by transforming how the $1T+ insurance industry allocates its largest spend: sales and distribution. Backed by a16z, we’re replacing legacy systems with a modern platform that allows carriers to automate workflows, optimize distribution spend, and unlock new growth. We have major fortune 500 insurers live and under contract. They’re already expanding.
At Chestnut, we operate with the belief that small, high-context teams working with best-in-class tools and colleagues can achieve outsized results. We embody what it means to be AI-lean: chasing 10x productivity gains that allow us to scale impact beyond our team size.
This is especially true in this builder function, where team members are running data migration scripts and shipping production PRs. We are building an AI-driven deployment engine, bringing down the time-to-value from the industry standard of quarters to that of weeks.
If you’re excited to realize the true impact of AI in one of America’s most essential industries, we’d love to meet you. Your work will accelerate a once-in-a-generation transformation.
From Chestnut Health Systems's careers page, first listed on Rolev.ai on November 12, 2026. Rolev.ai is not the employer.
How Rolev.ai helps with this application
Rolev.ai is a job search and application tool for US job seekers. For this Software Engineer (Mid-Level) role at Chestnut Health Systems, it shows how your resume fits, tailors your resume to the posting, and prepares the application for you to review.
See how you fit
Openings from employer career sites are ranked against your whole resume—and searchable inside Claude, ChatGPT, and Cursor via Rolev.ai MCP.
Tailor without inventing
Every change to your resume is checked against your original. New experience goes in only with your yes—zero fabricated claims.
Draft the full kit
Tailored and Full Match resumes, role-specific cover letters, and answers to employer screening questions are prepared in seconds.
1-Click Extension Autofill
The Chrome extension fills the employer's Greenhouse, Workday, Lever, or Ashby form in 1 click. You review it and press Submit.
Similar roles
All Software Engineer jobs- Software Engineer, Robot Diagnostics & CalibrationAgility Robotics · Onsite- Salem, OR
- Software Engineer, Backend (Partner 16, Partner 18)Andreessen Horowitz · San Francisco, CA
- Software Engineer - C++Akuna Capital · Chicago, IL
- Software Engineer - Early CareerNevada State Assembly · US > Arizona > Phoenix
- Software Engineer (Engineer III to Principal) - Formal MethodsCertik · New York, NY / Seattle, WA / San Francisco Ba…
- Software EngineerExtend · New York City, NY
Common questions
Where is the Software Engineer (Mid-Level) job at Chestnut Health Systems located?
Yes, this Software Engineer (Mid-Level) opening at Chestnut Health Systems is listed as San Francisco, CA (Remote). Always check Chestnut Health Systems's application page for specific state eligibility or relocation policies.
How do I apply for the Software Engineer (Mid-Level) position at Chestnut Health Systems?
This listing links directly to Chestnut Health Systems's Ashby application page. You can apply directly on Chestnut Health Systems's site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Ashby application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.