Director of Product Management

Role Description

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.

• 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.
• 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.

Qualifications

• 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.

Benefits

• Competitive salary and equity based on role.
• Policies and managers that support work/life balance, like our 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 and open to remote.
• Remote and WFH options, as well as a beautiful, state-of-the-art office in Dallas’ Deep Ellum, for those who prefer an office setting.
• Employee-led diversity, equity, and inclusion initiatives.