Product Manager - Workflows

Location Type: Remote Location: Remote US Employment Type: FullTime Department: Technology ABOUT OUTMARKET Outmarket is redefining how brokers, MGAs, and wholesalers operate by bringing an AI-first approach to insurance workflows. Our platform helps teams automate repetitive work, make better decisions, and scale more effectively across commercial insurance and employee benefits. We are building products in close partnership with customers and using AI where it creates real leverage, not just novelty. ABOUT THE ROLE We are hiring a Product Manager - Workflows to help design and ship product experiences that make complex insurance operations simpler, faster, and more scalable. This role is well suited for someone who can earn customer trust, translate ambiguity into crisp product decisions, and work closely with engineering to deliver practical AI-enabled workflows. This is not a role for someone who wants to manage tickets from a distance. You will be close to users, product tradeoffs, and the hard parts of turning AI into software people actually trust. WHY THIS ROLE - Work directly with users and turn real operational pain into product improvements. - Build AI-enabled workflow software with meaningful day-to-day customer impact. - Operate in a high-ownership environment with short feedback loops. - Partner closely with engineering and go-to-market teams to ship useful, polished features. - Help shape how AI is applied in a practical, trusted way within a traditional industry. WHAT YOU’LL DO - Work closely with users to understand operational pain points and translate them into product decisions. - Serve as a connective partner between go-to-market and engineering teams. - Design scalable workflow experiences that reduce manual effort and improve operational quality. - Partner with engineering to layer intelligence into key workflow steps. - Measure adoption, usage, and business impact, and iterate based on results. - Support pilot deployments, beta releases, and expansion into new lines by translating commercial needs into product priorities. - Make judgment calls in areas where customer need, product quality, and AI behavior all intersect. WHAT WE’RE LOOKING FOR - 5+ years of product management experience, with at least 2 years in B2B SaaS. - Experience working with engineering teams building AI-enabled products. - Comfort discussing how AI outputs are evaluated and how product design can build trust in AI behavior. - Strong use of AI tools in your own work to accelerate research, writing, and synthesis. - Strong written communication and the ability to explain product rationale clearly. - Strong UX instincts and the ability to simplify complex processes. - Comfort speaking with users, understanding operational pain, and designing practical solutions. - The ability to move quickly without getting sloppy. BONUS IF YOU HAVE - Direct experience working at or closely with a retail broker, wholesaler, or MGA. - Familiarity with commercial P&C lines or Employee Benefits. - Experience building document-processing or workflow automation products. - Comfort with SQL or basic data analysis. - Previous startup experience, especially in a Series A to Series C environment. WHAT YOU’LL GET - Real ownership of products that insurance teams rely on daily. - Competitive compensation and meaningful equity. - Direct access to users and strong influence on roadmap decisions. - A builder-oriented culture with fast execution and low ego. - Remote-first flexibility with a distributed, high-performing team.