QA Lead Software Engineer at Chestnut

At Chestnut, we are on a mission to modernize the massive insurance industry by building the first AI-native operating system for distribution. We are tackling a trillion-dollar market by replacing outdated legacy systems with a flexible, modern platform that helps carriers automate their most complex workflows. Backed by investors like a16z, our team is scaling rapidly as major insurers adopt our technology. We believe in the power of small, high-context teams that leverage the latest in agentic AI to achieve massive productivity gains. If you want to help us reshape the infrastructure of an essential industry, we would love to have you join our journey.

The opportunity

We are looking for our first QA Lead Software Engineer to join our team. This is a foundational role where you will have the autonomy to define our entire quality strategy from the ground up. You will be the primary architect for our testing processes, ensuring that our platform remains robust and reliable as we scale. By joining us as our first dedicated quality hire, you will play a critical role in shaping our engineering culture and setting the standards for how we deliver high-quality software to our customers.

A day in the life

• You will build our QA strategy, tools, and processes from scratch, ensuring they align with our fast-paced development cycles.
• You will design and implement a comprehensive automated test framework, primarily utilizing Playwright and TypeScript.
• You will collaborate closely with our engineering and product teams to integrate quality checks directly into our CI/CD pipelines and development workflows.

Who you are

You are an experienced engineer who thrives in environments where you can build things from the beginning. You have at least 5 years of experience in quality assurance, with at least 2 of those years spent in a lead or founding capacity. You are highly proficient in modern test frameworks and comfortable scripting in TypeScript or Python. Because we operate as a remote-first team, you are a clear and proactive communicator who can work independently while driving cross-functional initiatives. You have a deep understanding of CI/CD pipelines and a passion for determining the right balance between automated and manual testing.

Why you'll love it here

We are committed to supporting our team members both professionally and personally. When you join Chestnut, you will enjoy the following benefits:

• Equity compensation to ensure you share in our success.
• A remote-first work environment that prioritizes trust and autonomy.
• Regular company retreats to help us stay connected and bond as a team.
• A flexible paid time off policy so you can take the time you need.
• Comprehensive medical, dental, and vision insurance coverage.