Bestow

Lead new business experience strategy and manage product management team to deliver AI-native insurance solutions. | 10+ years product management with 5+ years leadership, expertise in insurance distribution, customer acquisition, and AI tools. | ABOUT BESTOW Life insurance is one of the world's most important products. It's also one of the hardest to build, distribute, and modernize. Bestow exists to change that. 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 isn't selling policies. We're building the infrastructure that helps an entire industry move faster, reach more people, and deliver on its promise. Backed by leading investors (Goldman Sachs, Hedosophia, NEA, Valar, 8VC) and trusted by major carriers, Bestow is powered by a team that moves with precision, purpose, and heart. If you want to help reimagine a centuries-old industry with lasting impact, join us. Bestow offers flexible remote/hybrid work, meaningful benefits, equity, and substantial growth opportunities. Bestow uses E-Verify to confirm the employment eligibility of all newly hired employees. To learn more about E-Verify, including your rights and responsibilities, please visit E-Verify.gov. ABOUT THE TEAM The Bestow Product organization is responsible for defining, designing, and delivering exceptional digital experiences that solve real problems. Our team collaborates across Engineering, Revenue and Ops teams to transform ideas into intuitive, valuable solutions that delight our users. We believe in evidence-based decision making and maintaining a relentless focus on customer outcomes to drive product excellence. This role reports into the VP, Product Management and is open to Remote (US). #LIRemote ABOUT THE ROLE 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. You'll lead and develop a team of product managers across three surfaces, 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. WHAT YOU’LL DO 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 Own the cross-module surface area with clear accountability across the funnel 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 WHO YOU ARE 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 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 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 Fortune’s Best Workplaces in Financial Services and Insurance 2022 + 2023 + 2024 We value diversity at Bestow. The company will hire, recruit, and promote regardless of race, color, religion, sex, sexual orientation, gender identity or expression, national origin, pregnancy or maternity, veteran status, or any other status protected by applicable law. We understand the importance of creating a safe and comfortable work environment and encourage individualism and authenticity in every team member. Thanks for considering a job at Bestow!

Lead product initiatives using AI tools and collaborate with teams to develop impactful features. | Requires 5+ years product management in B2B SaaS and a bachelor's degree. | ABOUT BESTOW Life insurance is one of the world's most important products. It's also one of the hardest to build, distribute, and modernize. Bestow exists to change that. 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 isn't selling policies. We're building the infrastructure that helps an entire industry move faster, reach more people, and deliver on its promise. Backed by leading investors (Goldman Sachs, Hedosophia, NEA, Valar, 8VC) and trusted by major carriers, Bestow is powered by a team that moves with precision, purpose, and heart. If you want to help reimagine a centuries-old industry with lasting impact, join us. Bestow offers flexible remote/hybrid work, meaningful benefits, equity, and substantial growth opportunities. Bestow uses E-Verify to confirm the employment eligibility of all newly hired employees. To learn more about E-Verify, including your rights and responsibilities, please visit E-Verify.gov. ABOUT THE TEAM The Bestow Product organization is responsible for defining, designing, and delivering exceptional digital experiences that solve real problems. Our team collaborates across Engineering, Revenue and Ops teams to transform ideas into intuitive, valuable solutions that delight our users. We believe in evidence-based decision making and maintaining a relentless focus on customer outcomes to drive product excellence. We're building at the intersection of insurance infrastructure and AI-native product development. The best candidates will come with a working relationship with AI tools already established — and a hunger to push that further. The role is remote or can be a hybrid role from our Dallas headquarters. #LI-Remote WHAT YOU'LL DO Bestow is looking for an exceptional Senior Product Manager who thrives on transforming complex challenges into elegant solutions. We're seeking a pioneer who can see beyond the immediate horizon – someone who combines strategic vision with tactical excellence to drive meaningful impact across their product area. This role is perfect for a product leader who understands that the most meaningful innovations often arise from the most perplexing problems. You'll be the driving force behind multiple high-impact initiatives, translating business objectives and customer needs into products that truly make a difference. Your ability to navigate ambiguity, inspire cross-functional teams, and deliver measurable results will be instrumental in advancing our mission to increase financial stability for everyone. As a Senior Product Manager at Bestow, you will: 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 WHO YOU ARE 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 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 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 Fortune’s Best Workplaces in Financial Services and Insurance 2022 + 2023 + 2024 We value diversity at Bestow. The company will hire, recruit, and promote regardless of race, color, religion, sex, sexual orientation, gender identity or expression, national origin, pregnancy or maternity, veteran status, or any other status protected by applicable law. We understand the importance of creating a safe and comfortable work environment and encourage individualism and authenticity in every team member. Thanks for considering a job at Bestow!