ABOUT OUTMARKET Outmarket is the AI platform for insurance, trusted by more than 250 brokerages to run the work their business depends on. Commercial insurance still runs on dense documents and slow, manual workflows, and that is exactly what we automate: quote comparisons, coverage gap and tower analysis, policy review, and proposal generation, all grounded in our customers’ own data and source-cited so teams can trust the output. The impact is concrete. Teams save 12 to 15 hours per person every week, cut errors by roughly 65 percent, and win more business, all on infrastructure that is SOC 2 Type II certified, single-tenant, and never used to train AI models. We are an AI-first company in both what we build and how we work, shipping quickly and in close partnership with the agencies that rely on us. WHAT YOU’LL GET A high-impact role with ownership from day one. Competitive compensation and meaningful equity. Direct collaboration with founders and real users. Remote-first flexibility. The opportunity to help build an AI-native product from the ground up. ABOUT THE ROLE We are hiring a Staff Software Engineer to provide technical leadership across teams without stepping out of the code. You will drive architecture for our most important systems, de-risk hard problems, and multiply the output of the engineers around you. WHY THIS ROLE Set the technical direction for systems that the whole product depends on. Solve the hardest cross-cutting problems in an AI-native platform. Influence how the entire engineering org builds, without managing people. WHAT YOU’LL DO Lead architecture for major systems spanning AI, data, backend, and frontend. Identify and remove the biggest technical risks and bottlenecks. Set engineering standards (design, testing, reliability, performance) and make them stick. Mentor senior engineers and raise the technical bar across teams. WHAT WE’RE LOOKING FOR 7+ years of software engineering, with a record of leading complex, cross-team systems. Deep system design expertise and strong hands-on coding ability. Demonstrated technical influence beyond your own direct work. Sound judgment about trade-offs, scope, and what to build vs. defer. BONUS IF YOU HAVE Experience scaling AI/ML systems or large data platforms. Early-stage startup or 0→1 product experience.