Senior Product Manager, Underwriting

Bestow is a leading vertical technology platform serving the life insurance industry, aiming to modernize and streamline the insurance process. They are seeking a Senior Product Manager, Underwriting to lead complex product initiatives, collaborate with clients and underwriters, and drive product excellence through AI integration.

Responsibilities:

• Lead complex product initiatives across underwriting, owning outcomes from problem definition through launch and adoption
• Partner directly with clients and underwriters to shape what the platform becomes — surfacing the capabilities they need, pressure-testing new features, and turning that input into a durable roadmap for platform evolution
• Leverage AI tools and agentic workflows as a core part of your product development process — from discovery and synthesis to roadmap communication and stakeholder prep
• Translate carrier requirements and regulatory constraints into product requirements that engineering can build against and underwriters can actually work in
• Develop and maintain product roadmaps that align with company strategy, balancing near-term capability gaps with long-term platform vision
• Model AI-native working habits for the broader team and contribute to Bestow's shared knowledge base of tools, skills, and workflows
• Identify opportunities for improvement through direct observation of underwriting workflows, data analysis, client feedback, and competitive intelligence
• Influence stakeholders across the organization by effectively communicating product vision, strategy, and outcomes
• Coach and mentor junior product managers while modeling Bestow's operating principles

Requirements:

• Bachelor's degree or equivalent experience
• 5+ years of product management experience
• Hands-on life insurance experience, ideally in or adjacent to underwriting — you've worked alongside underwriters and understand how a case actually moves
• Working familiarity with the underwriting toolkit: evidence and requirements, APS and lab data, carrier guidelines, and the judgment calls that sit between an application and a decision
• Experience building for expert users who make consequential decisions, where speed matters but accuracy and auditability matter more
• Demonstrated ability to lead multiple projects simultaneously across an entire product area
• Proven track record of delivering successful products with measurable business impact
• 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
• Experience with user research, usability testing, and UI/UX design principles for complex systems
• Comfortable building and managing personal context systems — loading information into AI tools effectively to produce higher-quality, faster outputs
• Strong analytical skills with experience using product analytics tools and BI solutions to drive decision making
• Understands the difference between AI as a search tool and AI as a reasoning partner, and operates accordingly
• Excellent communication and stakeholder management abilities, with demonstrated success influencing cross-functional teams
• Comfortable operating with ambiguity and making decisions with incomplete information
• Has a point of view on how AI changes the PM role — and is excited to help define what that looks like at Bestow