Founding Engineer

Job DescriptionFounding Engineer | Insure Stack\n\nAbout Us\nPrestige Trucking Insurance is a commercial trucking insurance agency specializing in fleets. We also own Insure Stack, an AI native operating system for insurance distribution serving 800+ agencies. Insure Stack automates commercial trucking and commercial auto quoting by working carrier portals and APIs in parallel, with one goal: quotes from every carrier, at the same time, in under ten seconds. The platform originated at a Y Combinator company.\n\nBecause Insure Stack lives inside an operating agency, you build right next to the people who quote trucking risks every day, and you see the impact of your work immediately.\n\nThe Role\nWe are looking for a builder who wants to take this product to the next level. You will own the platform end to end, work directly with leadership, and help decide where our technology goes next. You will be measured on growth and revenue as much as on code, and the scope of this role grows with the company.\n\nWhat You'll Do\n\n Own the core quoting engine and carrier automation layer, keeping it reliable and fast as we add carriers and volume\n Ship features that grow the business: new carriers, better conversion, faster quotes, new revenue streams\n Design and ship LLM pipelines that read submissions, extract risk data, and normalize quotes across carriers\n Build full stack in Python and Next.js, from database to UI\n Bring ideas to leadership on product, pricing, and growth, not just estimates\n Set the engineering standards and culture as the team grows\n\n\nWho You Are\n\n You Think Like a Business Owner. Every technical decision comes back to revenue, cost, and customers. You look for ways to grow the product and get it into more agencies, and you treat company time and money like your own. You bring opportunities to the table, not just tickets.\n You See Around Corners, Then Decide. Before you write code, you can tell us: if we build it this way, here is what could break, here is what it costs us later, and here is how long it really takes. You weigh it, make the call, and move. Analysis serves the decision; it never replaces it.\n You Don't Overpromise. Your estimates are honest, and you hit them. If something will take longer than leadership hopes, you say so up front, explain why, and offer the best path forward. You would rather commit to a realistic date and beat it than promise a fast one and miss it.\n You Move Fast and Build It Right. Our leadership moves fast and decides quickly. You keep pace without cutting corners. What you ship is tested, secure, and built to last, because rework is the slowest path of all.\n You Sweat the Details. In insurance, one wrong VIN, driver, or coverage limit means a bad quote. You catch it before it ships.\n You Understand Insurance, or Want to Master It. Experience in insurance or insurtech, ideally commercial trucking or commercial auto, is a strong plus. If you are new to the industry, you are eager to learn how submissions, carrier appetite, and agencies really work, and you will have a working agency to learn from.\n\n\nExperience\n\n A track record as a founding, solo, or early stage engineer\n Strong Python plus Next.js, React, and Node.js\n Hands on Playwright or browser automation in production\n Production LLM experience, including evaluation (Langfuse or similar)\n Clear communicator who explains technical tradeoffs in business terms\n\n\nOur Stack\nPython, Next.js, React, Node.js, Playwright, Neon (Postgres), Stripe, Resend, PostHog, Linear, GCP\n\nWhy Join\n\n A true founding role with real ownership over architecture and product\n Built inside an operating insurance agency, so you work with real users from day one\n Your work ships to hundreds of agencies\n A big, underserved market with a real problem to solve\n\n\nTo Apply\nSend your resume and a link to something you built on your own, outside of work. We weigh what you build unprompted more heavily than any title.