Director, Product Management – Underwriting

Bestow

Director of Product Management leading underwriting on Bestow's AI insurance platform. Shaping strategy and executing product roadmaps to innovate in the insurance sector.

Posted 6/1/2026full-timeRemote • 🇺🇸 United StatesLead💰 $225,000 - $250,000 per yearWebsite

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Hard Skills

product managementunderwriting product developmentmarket researchproduct discoverydata-driven decision makingstrategic planningmetrics definitionAI tools usagedecision workflowsrules engine

Soft Skills

leadershipcoachingmentoringinfluencing stakeholderscommunicationteam empowermentanalytical mindsetstrategic thinkingcollaborationproblem-solving

Tools & Technologies

AI toolsClaudeCursorLovableReplitbacklog management toolsproduct management softwaredata analytics platformsproject management toolscustomer relationship management (CRM)

Industry Keywords

insuranceinsurtechfinancial servicesregulated industriesproduct methodologiesbest practicescustomer insightsbusiness strategyexecutive alignmentcross-functional collaboration

About the role

Key responsibilities & impact

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

Requirements

What you’ll need

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.

Benefits

Comp & perks

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