Senior Software Engineer, AI-Driven Systems

Thimble was an early pioneer in insurtech. We built a digital-first way for small businesses to buy coverage by the job, month or year, and have since delivered more than 200,000 policies across the United States. We started direct-to-consumer as an MGA, but today, we’re focused on growing through brokers and distribution partners, bringing the same simple, fast experience to the agents who serve small businesses. Thimble is still evolving and is at the front of AI-native distribution with MCP technology paired with API distribution.

In 2023, Thimble was acquired by Arch Insurance, part of Arch Capital Group Ltd. (Nasdaq: ACGL), an S&P 500 company providing insurance, reinsurance and mortgage insurance worldwide. That gives us something rare: the speed, ownership and culture of a startup, with the balance sheet, stability and long-term commitment of one of the industry’s strongest insurers.

For more information, visit thimble.com.

Our unique culture is built around our six core values:

Be relentlessly creative. Question everything. Get to know the rules so well, you can use them in new ways. Be the industry’s compliant radicals.

Act. Move forward. Learn. You can only make a decision based on the best information you have – so make it.

Be ruthlessly precise. Disciplined. Sweat the small stuff.

Get to the point. Make it crystal clear. Cut everything else. It’s our job to make insurance easy – however hard that is for us.

Show up early and ready. Deliver on time or before. Make the most of your time, so others can make the most of theirs.

Treat every person, and their ideas, with respect. Cherish diversity.

Thimble is investing in the next generation of its platform, and this engineer helps lead that work. Our backend is built on Node.js microservices and event-driven architecture on AWS, and we are evolving it toward durable, explicitly orchestrated workflows, with AI-native tooling at the center of how we build.

This is a hands-on role: you’ll write, review, and ship production code every day, with AI agents as your primary build partner. You’ll also shape technical strategy and set the patterns the rest of the team builds on.

You’ll work in Node.js and TypeScript every day, so you need to be productive in them from the start.