Principal Software Engineer

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 Principal Engineer to set technical direction at the company level. You will own the architecture and technical strategy for our AI-native platform, make the highest-stakes engineering decisions, and serve as a force multiplier across the entire organization. WHY THIS ROLE - Define the long-term technical vision for an AI-native insurance platform. - Make the decisions that shape the product's foundation for years. - Work shoulder-to-shoulder with founders on company-defining problems. WHAT YOU'LL DO - Own architecture and technical strategy across AI, data, infrastructure, and product. - Drive the most consequential and ambiguous technical decisions to resolution. - Establish engineering principles and standards adopted org-wide. - Mentor staff and senior engineers and elevate the whole team's technical judgment. WHAT WE'RE LOOKING FOR - 10+ years of engineering with a record of org-wide technical leadership. - Mastery of system design and architecture at scale, with deep hands-on ability. - History of making high-stakes technical bets that paid off. - Exceptional judgment, communication, and the ability to align teams on direction. BONUS IF YOU HAVE - Deep experience with production AI/ML systems or large-scale data platforms. - Founding or early-stage technical leadership experience.