Senior Software Engineer, AI-Driven Systems

About Us 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 Values Our unique culture is built around our six core values: Think Wild, Act Tame 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. Green Means GO Act. Move forward. Learn. You can only make a decision based on the best information you have – so make it. Own Every Detail Be ruthlessly precise. Disciplined. Sweat the small stuff. Simplify, Simplify, Simplify Get to the point. Make it crystal clear. Cut everything else. It’s our job to ma