[Hiring] Lead Director, Medicare Product Knowledge & Enablement @CVS Health

Role Description

As a Lead Director within Benefit & Product Strategy and the Medicare Product Center of Excellence, you will build and lead a newly established strategic product knowledge and positioning function responsible for shaping how Medicare products and benefits are understood before they move into execution.

This role spans the Medicare Individual (IVL) portfolio, inclusive of all MAPD product types. It is intentionally focused on the strategy end of the product lifecycle—from benefit ideation and design through enterprise positioning and downstream handoff—ensuring teams responsible for execution are set up to deliver accurately, consistently, and in alignment with strategic intent.

This is a net new, highly autonomous role designed for a self-directed leader who can identify needs, set priorities, navigate a complex organization, and build a durable structure from the ground up. You will define the strategic narratives, positioning, guardrails, and source of truth product knowledge frameworks that enable downstream stakeholders to execute correctly.

This role is intentionally bi-directional. In addition to enabling downstream understanding, you will bring insights, risks, and improvement opportunities back to Benefit & Product Strategy to support evaluation, refinement, and continuous improvement of benefits, positioning, and future ideation.

Critically, this role will anchor product strategy in how Medicare products are brought to market—ensuring benefit design, positioning, and messaging are grounded in a deep understanding of how plans are sold, distributed, and selected by members across channels.

Key Responsibilities

• Establish and lead a new enterprise-wide knowledge enablement structure for IVL Medicare Advantage products.
• Translate complex benefit designs and product strategies into clear, consumable guidance for non-technical audiences.
• Partner with cross-functional teams—including Sales COE, Learning & Performance, Broker Communications, Care Management, Marketing, Operations, and Member Experience—to ensure product knowledge is accurately translated, strategically aligned, and consistently applied.
• Serve as a direct partner to Sales COE, supporting facilitation of product strategy conversations across internal and external distribution channels.
• Act as a trusted voice on Medicare Advantage IVL products, bringing deep product strategy and product operations knowledge to represent offerings with credibility and consistency.
• Integrate sales and distribution insights into product positioning, ensuring benefit narratives reflect how brokers, agents, and members evaluate, compare, and select plans.
• Partner closely with broker, agency, and field sales leadership to align product intent with go-to-market strategy.
• Establish and oversee a knowledge management framework, including playbooks, guidance materials, and centralized repositories.
• Ensure the appropriate artifacts exist to clearly communicate benefit intent, design rationale, and member impact to downstream stakeholders.
• Partner with Learning & Performance and other teams to inform training development.
• Ensure downstream functions have a clear, consistent understanding of product design, intent, and member impact.
• Provide subject matter expertise on how Medicare products are marketed and sold.
• Gather feedback from stakeholders, monitor effectiveness of enablement approaches, and adapt strategies to improve impact and adoption.
• Continuously assess competitive go-to-market strategies and sales enablement approaches across the industry.
• Influence leadership and stakeholders at all levels to drive alignment and adoption of product knowledge and positioning.
• Mentor and guide stakeholders in building strong, consistent product fluency across the organization.

Qualifications

• Willingness to travel for team meetings, industry and internal conferences, and internal sales forums (up to 30%).
• 10+ years of progressive experience in Medicare Advantage product management, strategy, or related functions.
• Deep knowledge of Medicare Advantage products, benefits, and regulatory requirements.
• Proven ability to translate complex product details into clear, consumable communications and trainings.
• Strong background in cross-functional leadership and enterprise collaboration.
• Demonstrated experience in building new processes or functions from the ground up.
• Exceptional written, verbal, and presentation skills, with a proven ability to engage diverse audiences.
• Demonstrated experience working in Medicare sales, distribution, or go-to-market functions.
• Deep understanding of Medicare distribution channels and how these channels influence product positioning and member choice.
• Practical knowledge of the end-to-end enrollment experience.

Preferred Qualifications

• Experience leading enterprise training, enablement, or knowledge management initiatives.
• Familiarity with broker training, care management engagement, or operations enablement.

Education

• Bachelor’s degree or equivalent experience required.

Benefits

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.
• Other resources, based on eligibility.

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.