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

Required Qualifications

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

Preferred Qualifications

Omni-channel retail or digital commerce experience, consulting

Background in personalization, targeting, or lifecycle marketing

MBA or advanced degree

Pay Range

The typical pay range for this role is:

$100,000.00 - $231,540.00

This pay range represents the base hourly rate or base annual full-time salary for all positions in the job grade within which this position falls. The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors. This position is eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above. This position also includes an award target in the company’s equity award program.

Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.

Great benefits for great people

We take pride in offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families.

This full‑time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well‑being of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility.

Additional details about available benefits are provided during the application process and on Benefits Moments.

We anticipate the application window for this opening will close on: 09/13/2026

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.

Learn more about this Employer on their Career Site

Lead Director Supplemental Benefit Engagement and Activation