Director, Product Management (New Business Experience) - Bestow

About Bestow

Life insurance is one of the world's most important products. It's also one of the hardest to build, distribute, and modernize. Bestow exists to change that.

Bestow is a leading vertical technology platform serving some of the largest and most innovative life insurers. Our platform unifies the fragmented, legacy value chain, enabling carriers to launch products in weeks instead of years. Carriers choose us to scale and operate at unprecedented speed, powered by AI and automation.

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.

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.

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 and stakeholder prep.
• Run rigorous discovery and backlog hygiene so engineering capacity is matched by a deep pipeline of ready-for-dev work.
• 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.
• 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.

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, or application products at a carrier, insurtech, or fintech.
• Strong understanding of insurance distribution (both agent/broker channels and direct-to-consumer flows).
• 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.
• Strong analytical mindset with experience defining metrics that matter and using data to drive decisions.
• Demonstrated ability to influence and align senior stakeholders.
• Experience in insurance, financial services, or highly regulated industries is a strong plus.

Total Rewards

• Competitive salary and equity based on role
• Flexible paid time off and parental leave programs
• 100% paid-premium option for medical, dental, and vision insurance
• Lifestyle stipend to support your physical, emotional, and financial wellbeing
• Flexible work-from-home policy