Vice President & General Manager, Medicare

eHealth

22d • Remote

About The Position

Join us in creating a better way! At eHealth, our mission is to expertly guide consumers through their health insurance and related options when, where, and how they prefer. We’re creating a better way – one that’s transparent and trustworthy for both our consumers externally and our employees internally. Move your career forward while connecting countless people to the life- changing, quality care they deserve. Our diverse team of innovators supports one another in solving some of the toughest challenges. We’re always on the lookout for creative opportunities to do right by our customers, and each other. Together, we’re creating a better way to work, united by our common passion to make a difference. Company Overview: eHealth is a leading health insurance marketplace connecting millions of consumers to affordable, high-quality coverage. Through partnerships with 180 carriers nationwide, we offer Medicare Advantage, Medicare Supplement, and Part D prescription drug plans — along with individual, family, small business, and ancillary products. As part of our next phase of growth, we are transforming from a transactional enrollment platform into the #1 digital + telephonic Medicare marketplace to help seniors not only enroll in coverage, but save money, improve access to care, better use their benefits and navigate healthcare year-round. We are seeking a bold, data-driven executive to serve as Vice President, Marketing & General Manager of Medicare to lead this transformation. Role Overview: As the Vice President & General Manager of the Medicare Business Unit, you will work closely with executive leadership and are responsible for growth strategies, performance, profitability and long-term value creation of the Medicare business. Reporting to the Chief Revenue Officer, the VP will: Lead integrated, omni-channel marketing orchestration and optimization Champion a seamless consumer experience across digital and telephonic journeys Expand high-margin marketplace services through strategic partnerships You will lead a cross-functional team to design, develop, and set operating goals, implement a roadmap of strategic initiatives, customer experience and marketing campaigns that deliver profitable growth, customer lifetime value (LTV) and retention.

Requirements

• 15+ years of senior leadership experience in general management, marketing, or both
• Ability to scale consumer businesses
• Deep experience in performance marketing and ROI optimization
• Healthcare or Medicare experience strongly preferred
• Experience managing large paid media budgets ($100M+)
• Strong financial acumen and operating plan management
• Data-driven decision maker with strong analytical capabilities
• Excellent leadership and team-building skills, with the ability to inspire and manage cross-functional teams to achieve business objectives.
• Exceptional communication and storytelling skills, able to articulate complex concepts concisely to various stakeholders.
• Strong project management skills, with the ability to juggle multiple priorities and ensure timely delivery across diverse teams and stakeholders.

Responsibilities

• Partner on building the forecast, and operating plan for the Medicare business unit
• Aligns SLT and Medicare business unit behind the translation of corporate strategy into business unit strategy, connected to the forecast and growth roadmap priorities
• Develop the business case for growth, investment and resource prioritization to deliver against the organization’s financial goals
• Lead cross functional teams through resource prioritization and initiative progress
• Regularly share business results, roadmap progress, any risks & opportunities with the Executive Leadership Team
• Define outcome goals, KPIs, and performance dashboards
• Deliver revenue growth, CAC efficiency, and LTV expansion
• Conduct market research and competitor analysis to stay ahead of industry trends, regulatory changes, and customer needs
• Drives investment and prioritization tradeoffs that maximize enterprise value
• Represent the Medicare business in executive reviews and planning forums
• Ensure operational readiness for new products, partnerships, and capabilities
• Oversee paid media budget exceeding $100M, driving profitable customer acquisition and engagement across TV, Direct Mail, Social, SEM, email, partners and emerging channels.
• Develop and execute a multi-year Medicare growth strategy
• Optimize full-funnel performance across ecommerce and telesales
• Leverage multi-touch attribution and marketing mix modeling
• Improve CAC while increasing lead quality and sales conversion
• Lead segmentation strategies across key Medicare audiences
• Build differentiated brand and creative platforms
• Oversee agency and vendor performance to ensure ROI and alignment
• Drive a culture of experimentation, testing, and data-driven optimization
• Ensure compliance with healthcare regulations and guidelines.
• Represent the consumer & brand voice in product, service, and process design
• Develop a deep understanding of consumer personas and leverage insights to refine and align messaging, targeting strategies and customer experience.
• Partner with Sales, Product, and Customer Care to reduce friction and increase conversion
• Connect digital and advisor-led interactions for consistency
• Develop lifecycle strategies that increase revenue and retention
• Ensure compliance with CMS and healthcare regulatory standards
• Develop business cases, negotiate strategic partnerships, oversee integration into digital and telesales workflows, and ensure strong financial returns.

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)

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed
• Number of Employees: 501-1,000 employees