Lead Director Supplemental Benefit Engagement and Activation

CVS Health · United States

We’re building a world of health around every individual — shaping a more connected, convenient and compassionate health experience. At CVS Health®, you’ll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger – helping to simplify health care one person, one family and one community at a time. Position Summary The Supplemental Benefits and Directed Spend Team at CVS is one of the fastest growing business units across the enterprise. It is uniquely situated at the center of our retail and healthcare business. We are looking for a dynamic and results-driven Director to lead Engagement & Activation. This role will own how members interact with and derive value from their supplemental benefits—driving activation, repeat engagement, and overall program performance. The ideal candidate will be highly adaptable, able to operate across strategy and execution, and act as a thought partner to enterprise leaders. This individual should demonstrate strong leadership, a member-first mindset, and the ability to influence outcomes across cross-functional teams.

• Own the Deals & Engagement Engine — the primary activation surface for supplemental benefits members, driving visibility, relevance, and performance
• Design and execute member engagement and activation strategies across Medicare, FSA/HSA, and Employer segments
• Partner closely with Product to shape the rewards, search, and shop experience from a member-first lens
• Lead development of personalization and targeting capabilities to improve deal relevance, conversion, and ongoing engagement
• Define and track KPIs for member activation, engagement, and retention; drive accountability across cross-functional teams
• Collaborate with Product, Marketing, Analytics, and Operations to identify and scale engagement opportunities across channels
• Translate insights and performance data into actionable strategies to improve member experience and program adoption
• Lead and develop a high-performing team, providing direction, coaching, and support to drive results
• Serve as a strategic thought partner to leadership, influencing roadmap decisions and long-term engagement strategy

• 10+ years’ experience in product, digital engagement, or related strategy roles, preferably in healthcare, retail, or fintech
• Strong leadership and management skills, with the ability to inspire and align cross-functional teams
• Demonstrated ability to design and execute engagement strategies that drive measurable outcomes
• Strong analytical mindset with experience defining KPIs and using data to inform decisions
• Excellent verbal and written communication skills, with the ability to influence senior stakeholders
• Bachelor’s degree

• Omni-channel retail or digital commerce experience, consulting
• Background in personalization, targeting, or lifecycle marketing
• MBA or advanced degree