Principal Product Manager

Job Summary

We are seeking an experienced Principal, Product Manager, to lead eHealth’s eCommerce insurance marketplace and online consumer shopping experience. The ideal candidate is a strategic product leader who thrives in complex environments and is passionate about improving customer outcomes in healthcare. 

You will design intelligent, personalized shopping experiences that clarify the historically challenging search for health insurance, earning consumer trust and maximizing conversion. This role will play a critical part in shaping the future of how online customers shop for healthcare by developing AI-first solutions. You will customize experiences for audience segments that range from brokers and employers seeking CHOICE (ICHRA) and traditional group coverage for their employees; individuals under 65 looking for individual and family plans; retirees turning 65 and aging into Medicare as well as individuals over 65 switching Medicare plans; and shoppers of all ages seeking gap and ancillary coverage (like dental, vision, and hearing) to supplement major medical coverage.

This role is responsible for defining the product strategy and roadmap, driving innovation across customer-facing experiences, and collaborating with cross-functional partners including engineering, data science, and business teams. Success in this role will be defined by the ability to improve the customer experience by delivering impactful product innovations and drive measurable business outcomes in a highly complex and evolving marketplace. 

Key Responsibilities

Drive eCommerce Vision & Roadmap: Own the enterprise website strategy, priorities and roadmap, leading the online shopping and enrollment experience, turning the search for health insurance coverage into an intuitive, guided, high-converting e-commerce experience, prioritizing initiatives that maximize conversion, Average Order Value (AOV), and lifetime customer value (LTV) based on customer retention.

Implement AI-Native Experiences: Define and launch consumer-facing AI agents, chat-based enrollment guides, and non-deterministic engines designed to empower users to effortlessly and transparently search for plans, cross-examine benefits, premiums, compare Rx drug and doctor coverage, and understand out-of-pocket costs. 

Architect Audience-First Segmentation: Establish framework models and global navigation paradigm that support users in dynamic audience segments based on roles (brokers, employers, individual shoppers), census and demographics, special needs like chronic conditions and dual-eligibility (Medicaid and Medicare), personal health intent and other criteria to trigger tailored e-commerce experiences.

Own Growth & Lifecycle Funnels: Oversee key growth metrics from conversion through digital marketing campaigns and organic entries through landing pages and educational experiences built in content management systems, dynamic shopping and enrollment experiences, activation, onboarding, lifecycle retention loops and support in concert with a trusted human advisor who can provide context to changes in plans and guidance as desired by the shopper.

Cross-Functional Collaboration and Leadership: Collaborate deeply with Sales and Marketing, UX Design, Data Science, Engineering, Legal and Compliance teams to ensure all consumer experiences, AI recommendation spaces maintain data integrity, legal compliance, and human trust.

Responsibilities include:

• Lead multi-year digital-commerce transformation initiatives spanning multiple product portfolios and business segments

• Serve as a strategic product advisor to senior executives, shaping investment priorities, portfolio tradeoffs, and own enterprise website roadmap

• Resolve complex dependencies and competing priorities across business and technology organizations

• Mentor product leaders and raise product-management capability through coaching, standards, and thought leadership

• Define and deliver enterprise-level outcomes across growth, customer trust, platform leverage, and long-term economics

• Define product requirements, write user stories, and manage backlog prioritization 

• Partner with cross-functional teams to identify dependencies and influence system architecture and design 

• Champion product vision and build alignment across internal and external stakeholders 

• Serve as Product Owner within Agile frameworks, participating in all Scrum ceremonies 

• Own UX optimization and A/B testing roadmap, including success criteria 

• Optimize product development processes to improve delivery speed, quality, and team impact, including website release governance, stage-gate reviews, and peak-period change management

• Be accountable for instrumentation, monitoring, issue prioritization, and risk escalation in partnership 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

Required and Preferred Qualifications

• 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

• Proven experience defining strategy, translating strategy into execution in a complex & matrixed organizational structure

• Strong domain familiarity with health tech, healthcare insurance workflows, or utilization mechanics is highly desirable but not mandatory if you bring world-class consumer marketplace expertise

• Experience going "zero-to-one" with generative AI products, prompt-engineered systems, or agentic automation workflows

• A high aesthetic standard for empathetic product interfaces, and polished mobile/desktop consumer user design.

• Analytical fluency with business metrics like conversion rates, drop-off analytics, and financial profitability frameworks 

• Bachelor’s or master’s degree in business, computer science, engineering, or related field 

• Experience serving as Product Owner in Agile frameworks (Scrum/Kanban) 

• Experience with tools such as Atlassian suite, Jira, Miro, Figma, and generative AI platforms (e.g., Copilot, Gemini, ChatGPT)

What we offer (benefits):

• Generous benefits include medical, dental and vision beginning on your first day of employment
• 401K with matching
• Tuition reimbursement
• Employee stock purchase program
• 12 company paid holidays and flexible time off (PTO for non-exempt)

*Please note the above is a summary of responsibilities; a full job description is available upon request. 

Application deadline: December 7, 2026.

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The base pay range reflects the anticipated pay range for this position. The actual base pay offered will depend on various factors including individual skills, experience, performance, qualifications, the department budget, and the location where work is performed. Base pay is one component of eHealth’s total rewards package, which also includes an annual performance bonus, plus an array of benefits designed to support employees’ personal and professional wellness. For more information on our total rewards offerings, please visit our career site.

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Base Pay Range -$182,400 - $243,200

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