Lead Director, Strategic Initiatives & Transformation

CVS Health; United States; Hybrid; USD 100,000 - 232,000; Full time

Benefits offered by this job

Medical, dental, and vision coverage

Paid time off

Retirement savings options

Wellness programs

Job summary

CVS Health is seeking a Lead Director, Strategic Initiatives to drive high-impact, cross-functional strategic efforts across Aetna Clinical Solutions, with remote/hybrid flexibility and preference for Central/East time zones. You will develop complex business cases, benchmark opportunities, and prepare executive decisions based on rigorous analysis.

The role demands senior-level advisory capabilities, structured problem solving, and the ability to influence leadership while delivering measurable

Qualifications

• 10+ years in management consulting, corporate strategy, strategic finance, or related disciplines.
• Led complex strategic assessments or enterprise-scale initiatives from problem definition through recommendation.
• Advanced analytical and structured problem-solving with financial analysis.
• Ability to operate in ambiguous environments and independently structure complex problems.
• Influence senior leaders and align stakeholders without direct authority.
• Exceptional executive communication, presentation, and storytelling skills.
• Ability to manage multiple high-priority initiatives concurrently.

Responsibilities

• Lead high-complexity and large-scale strategic initiatives with cross-functional analysis and executive engagement.
• Structure ambiguous business challenges, develop hypotheses, and translate findings into strategic recommendations.
• Develop rigorous strategic, operational, and financial assessments for new capabilities and investments.
• Benchmark and assess opportunities to improve performance and inform strategy.
• Lead opportunity development from problem definition to executive decision support.
• Collaborate with ACS leadership and stakeholders to evaluate strategic tradeoffs and risks.
• Prepare executive presentations, recommendations, and decision materials.

Skills

Strategic thinking

Executive communication

Cross-functional leadership

Financial analysis

Analytical problem solving

Stakeholder management

Problem structuring

Independent work

Education

Bachelor's degree

Master's degree preferred

Job description

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

We are open to location for this remote/hybrid opportunity, with a preference for qualified candidates in the Central or East time zones. The Lead Director, Strategic Initiatives will serve as a senior strategic advisor and individual contributor responsible for addressing high-priority, high-complexity business opportunities and challenges across Aetna Clinical Solutions (ACS). The role will lead the development of large-scale and complex business cases, strategic assessments, benchmarking, opportunity evaluation, and other executive-priority initiatives requiring rigorous analytical problem solving. Working across ACS and with enterprise partners, the Lead Director will structure ambiguous business problems, assess funding, resource capacity, delivery dependencies, and expected value, and translate fact-based recommendations into actionable plans and executive decisions. The role will also help establish the foundation for a broader internal strategic consulting capability within ACS.

Key Responsibilities

• Lead high-complexity and large-scale strategic initiatives and business cases requiring significant cross-functional analysis and executive engagement.
• Structure ambiguous business challenges, develop hypotheses and analytical approaches, and translate findings into actionable strategic recommendations.
• Develop rigorous strategic, operational, and financial assessments to evaluate new capabilities, investments, business opportunities, and transformation priorities.
• Conduct internal and external benchmarking and other fact-based assessments to identify opportunities to improve business performance and inform strategic direction.
• Lead opportunity development from initial problem definition through analysis, recommendation, and executive decision support.
• Partner with ACS leadership and cross-functional stakeholders to evaluate strategic alternatives, tradeoffs, risks, and organizational implications.
• Develop executive-level presentations, recommendations, and decision materials that simplify complex topics and clearly articulate strategic choices.
• Support high-priority executive requests and strategic projects where dedicated analytical leadership is required.
• Develop repeatable approaches, analytical frameworks, and problem-solving capabilities that establish the foundation for a future ACS internal consulting capability.
• Prepare and facilitate steering committees, leadership governance forums, and executive reviews for strategic initiatives, framing decisions, trade-offs, risks, and recommendations for leadership action.
• Incorporate funding, resource capacity, delivery dependencies, and expected value into strategic assessments and business cases so leadership can evaluate the full implications of major decisions.
• Identify opportunities to improve business performance through process optimization, automation, AI-enabled analytics, and productivity initiatives, and translate opportunities into actionable recommendations.

Required Qualifications

• 10+ years of progressive experience in management consulting, corporate strategy, strategic finance, business transformation, strategic planning, or related disciplines.
• Demonstrated experience leading complex strategic assessments, business cases, or enterprise-scale initiatives from problem definition through recommendation.
• Advanced analytical and structured problem-solving capabilities, including financial and quantitative analysis.
• Demonstrated ability to operate effectively in ambiguous environments and independently structure complex business problems.
• Strong business acumen with the ability to evaluate strategic, operational, and financial implications of potential decisions.
• Demonstrated ability to influence senior leaders and align stakeholders across organizational boundaries without direct authority.
• Exceptional executive communication, presentation, and storytelling capabilities.
• Ability to simultaneously manage multiple high-priority initiatives and changing leadership priorities.

Preferred Qualifications

• Management consulting or internal strategy experience.
• Healthcare or health insurance experience.
• Experience developing large-scale transformation business cases and strategic recommendations.
• Experience working with executive leadership on enterprise-level strategic priorities.
• Knowledge of clinical and health plan operations.

Education

• Bachelor's degree, or equivalent experience. Master's degree preferred.

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.

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: 01/12/2027

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

Our Work Experience is the combination of everything that's unique about us: our culture, our core values, our company meetings, our commitment to sustainability, our recognition programs, but most importantly, it's our people. Our employees are self-disciplined, hard working, curious, trustworthy, humble, and truthful. They make choices according to what is best for the team, they live for opportunities to collaborate and make a difference, and they make us the #1 Top Workplace in the area.