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.
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 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