Director, Product Management

WHAT YOU'LL DO

Bestow is looking for an exceptional Director of Product Management to lead Underwriting — one of the most consequential functions in our platform and a domain that directly shapes how our carrier partners assess risk and bring products to market. This is product leadership where strategic vision meets operational rigor: owning the strategy, roadmap, and execution for underwriting end to end.

You'll lead and develop a team of product managers, 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. You'll be both a strategist and an operator — comfortable shaping company-level direction with executives, and equally comfortable in the details of backlog hygiene, customer research, and roadmap trade-offs.

As a Director of Product Management, you will:

• Lead a high-performing team of product managers, setting clear priorities and empowering them to deliver exceptional results
• Own product strategy and vision for underwriting, aligning business objectives with market opportunities and customer needs
• 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
• Integrate tightly with internal SMEs as embedded partners in the cadence, not reactive consultants
• 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
• Develop and communicate compelling underwriting 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

WHO YOU ARE

• 10+ years of product management experience, with at least 5 years of leading and developing product managers.
• Direct experience building underwriting product at a carrier, reinsurer, or insuretech - rules engine, decision workflows, accelerated/automated underwriting, underwriter workbenches
• 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

TOTAL REWARDS

At Bestow, we’re proud to be awarded for our team members, innovative products, and culture. Our standard benefits include:

• 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