About Chestnut

Chestnut is building the first 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, flexible platform that helps carriers automate complex workflows, optimize every distribution dollar, and unlock new growth. We have major insurers under contract, and early adopters are expanding.

This is a generational platform shift. Recent advances in agentic AI make it possible to automate what was once manual and error-prone. We’ve spent years building the data model and context layer required to make this real, and now we’re scaling with urgency.

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 headcount.

If you’re excited to modernize the infrastructure of one of America’s most essential industries, we’d love to meet you. Whether shaping core product experiences or laying the groundwork for intelligent automation, your work will accelerate a once-in-a-generation transformation.

Job Description

We’re looking for a QA Lead Software Engineer to be our first QA hire and lay the foundation for quality engineering across the company.

This is a hands-on, high-impact role where you’ll define what QA looks like at Chestnut — from strategy to tooling to team growth. You’ll build our first test automation framework, champion quality across the stack, and play a key role in scaling our platform.

🔧 What You’ll Do

• Build Chestnut’s QA strategy, tools, and processes from the ground up

• Design and implement an automated test framework (we use Playwright + TypeScript)

• Define what should be automated — and what shouldn’t

• Work closely with engineering and product to integrate QA into our SDLC

• Own quality metrics, test plans, and defect tracking

• Set the stage for future QA team growth

🧠 What We’re Looking For

• 5+ years in QA, including 2+ years in a lead or founding QA role

• Strong with modern test frameworks (e.g., Playwright, Cypress, Selenium)

• Proficient in scripting (TypeScript, Python) and familiar with CI/CD pipelines

• Excellent communicator who can work cross-functionally and independently

• Experience building automation frameworks or processes from scratch

✅ Bonus Points

• Experience testing APIs and backend systems

• Familiarity with cloud platforms (AWS, GCP, Azure)

• Mobile testing experience

You’ll be joining a small, fast-moving team backed by top-tier investors (including a16z) and working on a product that’s transforming how insurance carriers operate.

Apply now to help define and lead QA at Chestnut.

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