We are redefining the operations of brokers, MGAs, and wholesalers at Outmarket. By leveraging an AI-first approach, our platform drives the evolution of the insurance industry, automating workflows and enabling scalable growth across employee benefits and commercial insurance sectors.

We’re hiring a curious and ambitious Product Manager who can earn a customer's trust, translate what they learn into crisp product decisions, and work shoulder-to-shoulder with engineering to ship AI that makes a meaningful impact. You’ll transform how the industry grows, operates, mitigates risk and makes decisions.

What You’ll Do

• You’ll work with real users from day one and iterate fast with short feedback loops.

• This is a high-ownership role in a fast-moving environment. You’ll serve as the connective tissue between our GTM and engineering teams, navigating ambiguity and making high-impact decisions to ship polished features fast.

• Translate industry knowledge into clean, scalable UX that cuts down manual effort

• Partner with engineering teams to layer intelligence into every step of the workflow.

• Measure adoption, usage, and impact, and iterate based on results

  Support deals and expansions

• Partner with GTM teams on pilot deployments, beta releases, and expansion into new lines, translating commercial needs into product requirements and vice versa.

What We’re Looking For

• 5+ years of product management experience, with at least 2 in B2B SaaS; experience in insuretech, fintech, or enterprise workflow software strongly preferred

• Hands-on experience working with engineering teams building AI products, comfortable discussing how AI outputs get evaluated, and how to design features that build trust in AI recommendations

• Habitual, fluent user of AI tools in your own day-to-day work, you reach for AI to accelerate research, writing, and synthesis, and you have well-developed instincts about where AI helps and where it falls short

• Strong writer, you communicate product rationale clearly in docs, Slack, and in the room with skeptical enterprise buyers

• Strong instincts for UX and an ability to simplify complex processes

• Clear communicator, fast executor, and strong cross-functional collaborator

• Comfortable talking to users, understanding real-world pain, and designing solutions

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 tools

• Comfort with SQL or basic data analysis, you can pull your own numbers when needed

• Prior startup experience (Series A–C); you know how to operate without a large support structure

What You’ll Get

• Real ownership of products that insurance teams rely on daily

• Competitive salary and meaningful equity

• Direct access to users and influence on roadmap decisions

• A builder’s culture: low ego, fast execution, and zero politics

• Remote-first setup with a globally distributed, high-performing team

Interested?
Send your resume or LinkedIn to careers@outmarket.ai
Include a short note explaining what excites you about the insurance broker workflow problem and what you'd want to build first.