Director, Product Management (Underwriting)

Bestow is a leading vertical technology platform serving some of the largest and most innovative life insurers. They are seeking an exceptional Director of Product Management to lead Underwriting, owning the strategy, roadmap, and execution for underwriting end to end while collaborating with senior leadership and managing a team of product managers.

Responsibilities:

• Lead a high-performing team of product managers, setting clear priorities and empowering them to deliver exceptional results
• Own product strategy and vision for underwriting, aligning business objectives with market opportunities and customer needs
• Leverage AI tools and agentic workflows as a core part of how you and your team operate — from discovery and synthesis to roadmap communication, stakeholder prep, and team coaching
• Model AI-native working habits and help define what product management looks like at an AI-native insurance platform
• Integrate tightly with internal SMEs as embedded partners in the cadence, not reactive consultants
• Lead market research, competitive analysis, and customer discovery to identify high-impact opportunities and inform strategic decisions
• Run rigorous discovery and backlog hygiene so engineering capacity is matched by a deep pipeline of ready-for-dev work
• Develop and communicate compelling underwriting roadmaps that balance immediate wins with transformative long-term bets
• Define success metrics and establish data-driven feedback loops to measure impact and guide continuous improvement
• Build persuasive business cases and influence senior stakeholders — Bestow executives, carrier-side executives, and cross-functional partners
• Partner with Engineering, Design, Marketing, and Operations to ship products our carriers and their customers depend on
• Coach and mentor product managers while modeling Bestow's operating principles, and help recruit world-class talent that raises the bar

Requirements:

• 10+ years of product management experience, with at least 5 years of leading and developing product managers
• Direct experience building underwriting product at a carrier, reinsurer, or insuretech - rules engine, decision workflows, accelerated/automated underwriting, underwriter workbenches
• Proven success owning and scaling a significant functional area or business domain from strategy through execution
• Deep expertise in product discovery, market research, and translating customer insights into winning strategies
• Actively uses AI tools (e.g., Claude, Cursor, Lovable, Replit, or equivalent) as a daily working accelerant — not just for writing, but for synthesis, research, and structured thinking
• Has a point of view on how AI changes the PM role and the PM org — and is excited to help define what that looks like at Bestow
• Strong analytical mindset with experience defining metrics that matter and using data to drive decisions
• Demonstrated ability to influence and align senior stakeholders—from enterprise customers to C-suite executives to cross-functional partners
• Experience establishing product methodologies, frameworks, and best practices that elevate team performance
• Track record of strategic planning that balances ambitious vision with pragmatic execution
• Experience in insurance, financial services, or highly regulated industries is a strong plus