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BestowBestow

Director, Product Management

Leads product strategy and a team of product managers across the full life-insurance enrollment funnel, from marketing handoff through policy bind. The role requires 10+ years of product management experience, people leadership, insurance or fintech distribution expertise, and daily use of AI tools.

About the job

Responsibilities

  • Lead and develop a high-performing team of product managers across Presales, Application, and Checkout.
  • Own product strategy and vision for the full enrollment funnel, from marketing handoff through policy bind.
  • Leverage AI tools and agentic workflows for discovery, synthesis, roadmap communication, stakeholder preparation, and team coaching.
  • Define AI-native product management practices and operating habits.
  • Own the cross-module surface area with clear accountability across the funnel.
  • Lead market research, competitive analysis, and customer discovery.
  • Run rigorous product discovery and backlog hygiene to maintain a pipeline of ready-for-development work.
  • Lead partner-facing product strategy for agents, agencies, and integrated distribution partners.
  • Develop and communicate roadmaps balancing immediate wins with long-term bets.
  • Define success metrics and data-driven feedback loops.
  • Build business cases and influence executives, carrier-side executives, and cross-functional partners.
  • Partner with Engineering, Design, Marketing, and Operations to deliver products.
  • Coach and mentor product managers and help recruit talent.

Requirements

  • 10+ years of product management experience.
  • At least 5 years leading and developing product managers.
  • Experience building customer acquisition, third-party distribution integrations, or application products in a carrier, insurtech, or fintech environment.
  • Strong understanding of insurance distribution through agent/broker and direct-to-consumer channels.
  • Experience owning and scaling a significant functional area or business domain from strategy through execution.
  • Expertise in product discovery, market research, and translating customer insights into strategy.
  • Daily experience using AI tools such as Claude, Cursor, Lovable, Replit, or equivalent for synthesis, research, and structured thinking.
  • Strong analytical mindset and experience defining meaningful metrics and using data to drive decisions.
  • Ability to influence and align enterprise customers, C-suite executives, and cross-functional partners.
  • Experience establishing product methodologies, frameworks, and best practices.
  • Strategic planning experience balancing ambitious vision with pragmatic execution.

Nice-to-haves

  • Experience in insurance, financial services, or other highly regulated industries.
  • A point of view on how AI changes the product management role and organization.

Compensation and Benefits

  • Competitive salary and equity based on role.
  • Flexible paid time off and parental leave.
  • 100% paid-premium option for medical, dental, and vision insurance.
  • Lifestyle stipend supporting physical, emotional, and financial wellbeing.
  • Flexible work-from-home and remote options.
  • Optional office setting in Dallas’ Deep Ellum.

Skills

Product Management, Product Strategy, Product Discovery, Market Research, Competitive Analysis, Artificial Intelligence, Agentic Workflows, Roadmapping, Backlog Management, Customer Acquisition, Insurance Distribution, Data Analytics, Metrics Definition, Third-Party Integrations, Stakeholder Management

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