Director, Product Management (New Business Experience)

Bestow is a leading vertical technology platform serving some of the largest and most innovative life insurers. Our platform unifies the fragmented, legacy value chain, enabling carriers to launch products in weeks instead of years. Carriers choose us to scale and operate at unprecedented speed, powered by AI and automation. Bestow is building the infrastructure that helps an entire industry move faster, reach more people, and deliver on its promise.

About the Team

The Bestow Product organization is responsible for defining, designing, and delivering exceptional digital experiences that solve real problems. The team collaborates across Engineering, Revenue, and Ops teams to transform ideas into intuitive, valuable solutions that delight users. We believe in evidence-based decision making and maintaining a relentless focus on customer outcomes to drive product excellence. This role reports to the VP of Product Management and is open to remote candidates in the US.

About the Role

Bestow is looking for an exceptional Director of Product Management to lead the New Business Experience: the full acquisition journey from marketing handoff through policy bind, spanning Presales, Application, and Checkout. This role blends strategic vision with operational rigor, owning the strategy, roadmap, and execution for how prospects become policyholders on our platform.

Responsibilities

• 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 operations—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.

Requirements

• 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.
• Flexible paid time off and parental leave programs.
• 100% paid-premium option for medical, dental, and vision insurance.
• Lifestyle stipend to support physical, emotional, and financial wellbeing.
• Flexible work-from-home policy and open to remote.
• State-of-the-art office in Dallas’ Deep Ellum for those who prefer an office setting.
• Employee-led diversity, equity, and inclusion initiatives.

Recent employer awards include: Best Place for Working Parents (2023, 2024, 2025), Great Place to Work Certified (2022, 2023, 2024, 2025), Built In Best Places to Work (2022, 2023, 2025), Fortune’s Best Workplaces in Texas (2022, 2023), and Fortune’s Best Workplaces in Financial Services and Insurance (2022, 2023, 2024).