QA Lead Software Engineer (Founding Role)

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