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 DescriptionWe’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 DoBuild 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.
BenefitsCompetitive 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
Top Skills
What We Do
Chestnut is on a mission to overhaul the insurance industry's technology and data infrastructure.
Our first product is a customizable, easy-to-use, and centralized producer management and compensation system that is purpose-built for the insurance industry. By using our cloud native platform, carriers and their distribution partners can free themselves from operational constraints imposed by legacy software, static compensation structures, and manual processes. We unlock growth opportunities by giving our customers the flexibility and insights needed to manage commissions as a revenue driver instead of as a cost-center and by enabling our customers to better engage with and retain their agents through our mobile-first agent app.
We have raised a seed round from notable investors including Andreessen Horowitz, Liquid 2 Ventures, and Detroit Venture Partners to achieve our mission.
