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 Forward Deployed AI Engineer to work directly with customers (brokers, MGAs, and carriers) to deploy and tailor our AI solutions to their real workflows. You sit at the intersection of engineering and the customer, turning messy real-world requirements into shipped, working systems. WHY THIS ROLE Own customer outcomes end to end, from problem to deployed solution. Work hands-on with real insurance data and source systems. Be the technical bridge between customers and the core product team. WHAT YOU’LL DO Deploy and configure AI-powered workflows for specific customers and source systems. Integrate with agency management systems and customer data, and resolve real-world data issues. Build tooling and feed product requirements back into the core platform. Partner with sales and customer success to ensure customers succeed. WHAT WE’RE LOOKING FOR 2+ years in software/forward-deployed/solutions engineering. Strong Python and SQL, and comfort debugging messy integrations. Customer-facing instincts and excellent communication. Bias to action in ambiguous, fast-moving situations. BONUS IF YOU HAVE Insurance, fintech, or other regulated-data domain experience. Experience with LLM-based systems or document processing.