Remote (Global)

Chestnut is hiring a QA Lead Software Engineer (Founding Role)

About the Role

Chestnut is looking for a QA Lead Software Engineer to step into its first and founding quality role. You will lay the foundation for quality engineering across the company, defining strategy, tooling, and processes from the ground up. This role is crucial for building the initial test automation framework and 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 using Playwright + TypeScript.
  • Define what should be automated — and what shouldn’t.
  • Work closely with engineering and product to integrate QA into the 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.
  • 2+ years in a lead or founding QA role.
  • Strong experience with modern test frameworks like Playwright, Cypress, or Selenium.
  • Proficient in scripting with TypeScript or Python.
  • Familiar with CI/CD pipelines.
  • Excellent communicator who can work cross-functionally and independently.
  • Experience building automation frameworks or processes from scratch.

Nice to Have

  • Experience testing APIs and backend systems.
  • Familiarity with cloud platforms like AWS, GCP, or Azure.
  • Mobile testing experience.

Technical Stack

  • Playwright
  • TypeScript
  • Python
  • CI/CD pipelines

Team & Environment

You will be the first QA hire, joining a small, fast-moving team.

Benefits & Compensation

  • Competitive salary and equity, with a 10 year exercise window for stock options.
  • Remote-first culture built on trust, autonomy, and high performance.
  • Team offsites.
  • Take what you need vacation policy.
  • Top notch health, dental, and vision insurance subsidized by the company.

Work Mode

This is a remote-first position.

Chestnut is an equal opportunity employer.

Required Skills
PlaywrightTypeScriptPythonCI/CDTest AutomationQuality AssuranceTesting StrategyAPI TestingPerformance TestingSecurity TestingTeam LeadershipProcess Improvement
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About company
Chestnut
Chestnut is building the first AI-native operating system for insurance distribution, transforming how the $1T+ insurance industry allocates its largest spend: sales and distribution. It replaces legacy systems with a modern, flexible platform that helps carriers automate complex workflows, optimize distribution spending, and unlock new growth.
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Job Details
Category qa_testing
Posted 9 months ago