Medicare Strategy Director Jobs (NOW HIRING)

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 ourselvesaccountable 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 Executive Director, Medicare Strategy, Finance & Value Creation is responsible for improving strategic decision-making, strengthening investment discipline, and accelerating value creation across the Medicare business.

Partnering directly with the Vice President, CFO Medicare and other senior leaders, this role will help build and lead a new Strategy, Finance & Value Creation capability focused on the organization's most important opportunities, investments, and business challenges. The team will provide rigorous analysis, strategic insight, and objective recommendations that improve the quality of executive decision-making and drive measurable business outcomes.

This role is ideal for a strategic leader who combines financial expertise, analytical rigor, executive influence, and a builder's mindset.

Major Responsibilities

Strategic Decision Support

• Serve as a trusted advisor to executive leadership on high-impact strategic, financial, and operational decisions.
• Lead analyses of growth opportunities, investments, partnerships, business model changes, transformation initiatives, and other enterprise priorities.
• Develop clear, decision-ready recommendations that balance financial performance, strategic objectives, operational feasibility, and risk.
• Translate complex data and analyses into concise executive communications and presentations.

Value Creation & Investment Governance

• Identify, assess, and prioritize opportunities to improve business performance and enterprise value.
• Establish frameworks for business case development, investment evaluation, and portfolio prioritization.
• Support resource allocation decisions by evaluating competing investments and strategic alternatives.
• Partner with business leaders to define expected outcomes, success measures, and value realization plans.
• Monitor performance against approved business cases and strategic objectives.

Strategic Planning & Future Insights

• Support development of Medicare's long-term strategy and value creation agenda.
• Lead scenario planning related to market developments, regulatory changes, competitive dynamics, and emerging opportunities.
• Identify risks and opportunities that may impact future business performance.
• Provide forward-looking insights that strengthen organizational preparedness and decision confidence.

Capability Building & Leadership

• Partner with the Vice President, CFO Medicare to establish and scale the Strategy, Finance & Value Creation organization.
• Help define the team's operating model, governance processes, prioritization framework, and measures of success.
• Recruit, develop, and retain high-performing talent.
• Foster a culture of analytical rigor, intellectual curiosity, collaboration, and accountability.
• Build strong relationships across Finance, Operations, Product, Network, Clinical, Technology, and Corporate Strategy.

Required Qualifications

• 10+ years of progressive experience in strategic finance, corporate strategy, management consulting, corporate development, business transformation, healthcare strategy, or a related field.
• Experience within healthcare, health insurance, managed care, Medicare, or a closely related industry.
• Demonstrated ability to influence executive decision-making through strategic analysis and business insight.
• Strong financial modeling, business case development, scenario planning, and problem-solving capabilities.
• Experience leading complex cross-functional initiatives involving senior stakeholders.
• Exceptional communication, presentation, and relationship-management skills.
• Proven success building and leading high-performing teams.

Preferred Qualifications

• MBA, MHA, MPH, CPA, CFA, or other relevant advanced degree or professional certification.
• Medicare Advantage experience.
• Experience in corporate strategy, management consulting, strategic finance, transformation, corporate development, or value creation.
• Experience building new teams, capabilities, governance models, or strategic planning functions.
• Track record of developing investment governance or value realization disciplines.

Pay Range

The typical pay range for this role is:

$131,500.00 - $303,195.00

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 fulltime position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial wellbeing 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: 10/02/2026

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