Principal Product Manager

eHealth

1d•$182,400 - $243,200•Remote

About The Position

eHealth is seeking an experienced Principal Product Manager to lead its eCommerce insurance marketplace and online consumer shopping experience. The role will define product strategy and roadmap and shape personalized, AI-first experiences that make health insurance shopping clearer, more trustworthy, and more effective for consumers. Audiences include brokers and employers seeking CHOICE (ICHRA) and traditional group coverage; individuals and families under 65; people approaching or enrolled in Medicare; and shoppers seeking supplemental dental, vision, hearing, and other gap coverage. The Principal Product Manager will drive innovation across customer-facing experiences and work closely with engineering, data science, business, design, sales, marketing, legal, and compliance partners. The role is accountable for improving customer outcomes and trust while delivering measurable business results in a complex, evolving marketplace. It also provides strategic product leadership across portfolios, advises senior executives on investments and tradeoffs, mentors product leaders, and improves product-management practices and delivery processes.

Requirements

10+ years of product management leadership and a track record of deploying large-scale consumer e-commerce storefronts, dual-sided marketplace engines, or complex fintech platforms with cross-functional partners.
Demonstrated ability to define strategy and translate it into execution in a complex, matrixed organization.
Experience developing products from zero to one using generative AI, prompt-engineered systems, or agentic automation workflows.
High aesthetic standards for empathetic product interfaces and polished mobile and desktop consumer design.
Analytical fluency with business metrics such as conversion rates, drop-off analytics, and financial profitability frameworks.
Bachelor’s or master’s degree in business, computer science, engineering, or a related field.
Experience serving as Product Owner in Agile frameworks such as Scrum or Kanban.
Experience with tools such as the Atlassian suite, Jira, Miro, Figma, and generative AI platforms such as Copilot, Gemini, or ChatGPT.

Nice To Haves

Strong familiarity with health technology, healthcare insurance workflows, or utilization mechanics; this is desirable but not mandatory for candidates with world-class consumer marketplace expertise.

Responsibilities

Own the enterprise website strategy, priorities, and roadmap, leading online shopping and enrollment experiences and prioritizing initiatives that improve conversion, average order value, and customer lifetime value.
Define and launch consumer-facing AI agents, chat-based enrollment guides, and other AI-driven tools that help consumers search for plans, compare benefits and premiums, review prescription drug and doctor coverage, and understand out-of-pocket costs.
Create audience segmentation frameworks and navigation models that tailor e-commerce experiences to user roles, demographics, health needs, and intent.
Oversee growth and lifecycle funnels, including marketing and organic landing pages, educational content, shopping and enrollment, activation, onboarding, retention, and support alongside human advisors.
Collaborate with Sales and Marketing, UX Design, Data Science, Engineering, Legal, and Compliance to maintain data integrity, legal compliance, and consumer trust.
Lead multi-year digital-commerce transformation initiatives across product portfolios and business segments.
Advise senior executives on investment priorities and portfolio tradeoffs, and own the enterprise website roadmap.
Resolve dependencies and competing priorities across business and technology organizations.
Mentor product leaders and improve product-management capability through coaching, standards, and thought leadership.
Define and deliver enterprise outcomes across growth, customer trust, platform leverage, and long-term economics.
Define product requirements, write user stories, and prioritize the backlog.
Identify cross-functional dependencies and influence system architecture and design.
Champion product vision and build alignment among internal and external stakeholders.
Serve as Product Owner in Agile frameworks and participate in Scrum ceremonies.
Own the UX optimization and A/B testing roadmap, including success criteria.
Improve product development processes, delivery speed, and quality, including website release governance, stage-gate reviews, and peak-period change management.
Oversee instrumentation, monitoring, issue prioritization, and risk escalation with Analytics and Engineering.
Establish website platform and domain governance, accessibility, and legal and compliance coordination.
Communicate product performance, metrics, and roadmap updates to stakeholders.
Conduct market research and competitive analysis to inform product strategy.
Use data-driven decision-making to prioritize initiatives and measure success.