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