Director of AI-Driven Enrollment Platform

Bestow; Northern (KY); Hybrid; USD 180,000 - 280,000; Full time

Benefits offered by this job

Equity

Flexible PTO

Parental leave

Medical, dental, and vision insurance

Wellbeing stipend

Remote work policy

Job summary

Bestow is seeking a Director of Product Management to lead New Business Experience, spanning Presales, Application, and Checkout. You will own strategy, roadmaps, and execution for how prospects become policyholders on our AI-powered platform.

You'll guide a three-surface team, shape discovery, and translate complex regulatory challenges into elegant solutions. This role reports to the VP of Product Management and is open to Remote (US).

Qualifications

• 10+ years of product management experience with 5+ years leading PMs.
• Direct experience building customer acquisition and third-party distribution integrations.
• Strong understanding of insurance distribution channels and integration surfaces.
• Proven ability to scale a significant functional area from strategy to execution.
• Expertise in product discovery, market research, and translating insights into winning strategies.
• Active use of AI tools daily to accelerate discovery, synthesis, and roadmapping.
• POV on AI-driven PM org and helping define it at Bestow.
• Strong analytical mindset with metrics-driven decision making.

Responsibilities

• Lead a high-performing team of product managers with clear priorities.
• Own product strategy for the full enrollment funnel across channels.
• Leverage AI tools as a core part of discovery, roadmap communication, and coaching.
• Model AI-native working habits and define PM practices for an AI insurance platform.
• Own cross-module surface area with clear accountability across the funnel.
• Lead market research, competitive analysis, and customer discovery to identify opportunities.
• Conduct rigorous discovery and backlog hygiene to align engineering capacity.
• Lead partner-facing strategy for third-party distribution channels (agents, agencies, partners).
• Develop and communicate roadmaps balancing quick wins with long-term bets.
• Define success metrics and data-driven feedback loops to guide improvements.
• Build business cases and influence senior stakeholders across executives and partners.
• Collaborate with Engineering, Design, Marketing, and Operations to ship carrier-facing products.
• Coach PMs and recruit world-class talent aligned with Bestow's operating principles.

Skills

Product management leadership

AI tooling usage

Cross-functional collaboration

Insurance/insurtech/fintech domain

Strategy & roadmapping

Tools

Claude

Cursor

Lovable

Replit

Job description

Bestow is seeking a Director of Product Management to lead New Business Experience, spanning Presales, Application, and Checkout. You will own strategy, roadmaps, and execution for how prospects become policyholders on our AI-powered platform.

You'll guide a three-surface team, shape discovery, and translate complex regulatory challenges into elegant solutions. This role reports to the VP of Product Management and is open to Remote (US).