Senior Product Manager

Bestow is a leading vertical technology platform focused on modernizing life insurance. They are seeking a Senior Product Manager who will lead complex product initiatives, leveraging AI tools to create compelling product features and enhance user experiences.

Responsibilities:

• Lead complex product initiatives across your area
• 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
• Design products and features with AI-assisted experiences in mind, understanding how agents, automation, and intelligent systems change user expectations
• Collaborate with cross-functional teams to translate customer needs and business objectives into compelling product features and experiences
• Develop and maintain product roadmaps that align with company strategy, balancing short-term wins with long-term vision
• Define success metrics and build data-driven feedback loops to measure product performance and inform future decisions
• 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 product improvements through customer research, market analysis, and competitive intelligence
• Partner with Engineering, Design, Marketing, and Operations to ensure successful product delivery and adoption
• 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 in B2B SaaS
• 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