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!
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.
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
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
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.
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
Welcome to Chestnut, where we are on the cutting edge of transforming the insurance industry! We're excited to share that we're looking for a QA Lead Software Engineer to join our founding team. This isn't just any QA role; you'll be our first dedicated QA hire, laying the groundwork for quality engineering in an innovative environment. In this hands-on position, you’ll define what QA will look like at Chestnut, developing everything from our QA strategy to the necessary tooling and processes. Imagine being in the driver's seat as you build our initial test automation framework using Playwright and TypeScript, shaping our commitment to quality across our platform. You’ll collaborate closely with both engineering and product teams to seamlessly embed QA in our software development lifecycle (SDLC), ensuring that our systems are not just functional but exemplary. We’re searching for someone with at least 5 years of QA experience and a couple of years in a leadership role. If you've got strong expertise with modern test frameworks and a knack for scripting, you’ll fit right in! Plus, we value great communication skills as you’ll be working cross-functionally. If you also have experience with mobile testing or cloud platforms, that's a bonus. Join us at Chestnut to help redefine QA and work on a product that truly makes a difference. We're a remote-first team backed by top-tier investors, committed to your growth with competitive salaries and benefits like unlimited PTO. Let's innovate together!
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