Remote (Global)

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

Responsibilities

  • Establish the foundational QA strategy, tooling, and processes
  • Develop and maintain an automated testing framework using Playwright and TypeScript
  • Determine appropriate scope and boundaries for test automation
  • Collaborate with engineering and product teams to embed QA practices into the software development lifecycle
  • Manage quality measurement, test planning, and tracking of defects
  • Lay the foundation for scaling a dedicated QA team in the future

Requirements

  • Minimum of 5 years of experience in quality assurance, with at least 2 years in a leadership or founding QA capacity
  • Proven expertise with modern test automation tools such as Playwright, Cypress, or Selenium
  • Strong scripting skills in TypeScript or Python and experience with CI/CD systems
  • Clear and effective communication skills for cross-functional collaboration and independent work
  • Hands-on experience building test automation frameworks or QA processes from inception

Nice to Have

  • Background in testing APIs and backend services
  • Knowledge of cloud infrastructure platforms like AWS, GCP, or Azure
  • Experience conducting mobile application testing

Benefits

  • Competitive compensation package including equity with a 10-year stock option exercise window
  • Remote-first workplace emphasizing trust, autonomy, and performance
  • Periodic team offsites to strengthen collaboration and relationships
  • Unlimited vacation policy with flexibility to take what you need
  • Comprehensive health, dental, and vision coverage with employer subsidies

Compensation

Competitive salary and equity, with 10 year exercise window for stock options

Work Arrangement

Remote-first culture built on trust, autonomy, and high performance

Team

small, fast-moving team

Other

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.

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 other
Posted a year ago