Director of Product Management

ABOUT THE ROLE

Bestow is looking for an exceptional Director of Product Management to lead New Business Experience: the full acquisition journey from marketing handoff through policy bind, spanning Presales, Application, and Checkout. This is product leadership where strategic vision meets operational rigor: owning the strategy, roadmap, and execution for how prospects become policyholders on our platform.

You'll lead and develop a team of product managers across three surfaces, set the bar for discovery and delivery, and partner with senior leadership across Bestow to translate complex regulated-industry challenges into elegant, AI-native solutions. You'll be both a strategist and an operator, comfortable shaping company-level direction with executives and equally comfortable in the details of backlog hygiene, customer research, and roadmap trade-offs.

WHAT YOU’LL DO

• Lead a high-performing team of product managers, setting clear priorities and empowering them to deliver exceptional results
• Own product strategy and vision for the full enrollment funnel, aligning business objectives with carrier priorities, agent needs, and customer experience
• 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
• Own the cross-module surface area with clear accountability across the funnel
• 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
• Own the cross-module surface area with clear accountability across the funnel
• Lead partner-facing product strategy for third-party distribution channels (agents, agencies, and integrated distribution partners)
• Develop and communicate compelling 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

WHO YOU ARE

• 10+ years of product management experience, with at least 5 years of leading and developing product managers.
• Direct experience building customer acquisition, third-party distribution integrations, application product at a carrier, insurtech, or fintech
• Strong understanding of insurance distribution (both agent/broker channels and direct-to-consumer flows) and the integration surface that connects them
• 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