Principal Product Manager

Role overview

Set product strategy for an online insurance marketplace and guide the evolution of its consumer shopping and enrollment experience. The role aims to make complex coverage choices clearer through personalized, trustworthy digital journeys, including AI-enabled tools, while improving customer outcomes and measurable business performance. Audiences include individuals, families, retirees, employers, and brokers shopping across major medical and supplemental coverage.

Responsibilities

- Own the digital commerce vision, priorities, and roadmap across shopping and enrollment experiences. - Design AI-enabled agents and conversational guidance that help shoppers find plans, compare benefits and costs, and understand coverage trade-offs. - Create audience segmentation and navigation approaches that tailor experiences to shoppers’ roles, demographics, needs, and health-related context. - Guide growth and lifecycle journeys from marketing entry points and educational content through shopping, enrollment, onboarding, retention, and support. - Lead multi-year transformation work across product portfolios and business segments, advising senior stakeholders on product direction. - Partner with engineering, design, data science, sales, marketing, legal, and compliance teams to deliver usable, measurable, and trustworthy experiences. - Use conversion, drop-off, customer retention, and financial performance measures to prioritize and assess product work.

Requirements

- Strong product leadership in complex environments and experience translating strategy into execution across a matrixed organization. - Expertise in consumer digital commerce or marketplace experiences, with a high standard for empathetic, polished mobile and desktop design. - Analytical fluency with conversion, funnel, and profitability measures. - Experience serving as a Product Owner in Agile methods such as Scrum or Kanban. - Ability to collaborate across business, design, engineering, data, and compliance functions. - Bachelor’s or master’s degree in business, computer science, engineering, or a related field.

Nice to have

Healthcare technology, insurance workflows, or utilization knowledge; experience launching generative AI products or agentic workflows; familiarity with Jira, Miro, Figma, and generative AI platforms.

Benefits and work setup

The role is listed as remote. Benefits include medical, dental and vision coverage, retirement matching, tuition reimbursement, an employee stock purchase program, paid holidays, and flexible time off.