Lead Director, Strategic Planning, Proposals

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

Benefits offered by this job

Bonus program

Equity award program

Comprehensive benefits

Job summary

CVS Health is seeking a seasoned leader to design and maintain a Medicaid governance model, guiding annual and multi-year planning cycles. You will work with senior leaders to translate strategy into measurable goals, KPIs, and execution plans.

You will collaborate across cross-functional teams to ensure alignment with enterprise objectives, with a focus on governance forums, risk management, and transparent decision-making.

Qualifications

• Minimum 10 years in a highly regulated healthcare environment.
• Minimum 3 years in Strategic Business Planning/PMO functions.
• Strong ability to synthesize complex information into strategic insights.
• Experience partnering with senior executives and leading cross-functional planning.

Responsibilities

• Design and maintain a Medicaid proposal governance model with defined decision rights and accountability.
• Establish governance forums with charters, cadence, and outcomes.
• Prepare strategic reviews, facilitate discussions, capture decisions and actions.
• Lead annual and multi-year strategic planning cycles and identify pillars and initiatives.
• Translate strategy into actionable roadmaps, milestones, and dependencies.
• Collaborate with senior leaders to turn objectives into measurable KPIs and plans.
• Ensure governance decisions consider financial, regulatory and operational factors.
• Mentor junior colleagues in related techniques and processes.

Skills

Regulated healthcare

Strategic planning/PMO

Analytical skills

Executive communication

Executive dashboards

CVS Health governance

Education

Bachelor's degree

Tools

Microsoft Office

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

Design and maintain a Medicaid governance model. Lead annual and multi‑year strategic planning cycles. Acts independently to address issues, guide direction, and provide analysis for planning initiatives. A Brief Overview Facilitates the design, implementation, and continuous improvement of a strong management and governance framework that drives strategic alignment, accountability, transparency, and effective decision‑making across the Medicaid proposal organization. Establishes clear operating rhythms, governance forums, and management processes to ensure priorities are executed efficiently, risks are managed proactively, and outcomes are measurable and aligned to enterprise goals. Leads the development, integration, and execution of the Medicaid proposals strategic plan. Acts independently to address issues, guide direction, and provide analysis for planning initiatives.

What you will do

Design and maintain a Medicaid proposal governance model that defines decision rights, escalation paths, roles, and accountabilities. Establish and facilitate governance forums (e.g., leadership reviews, operating committees) with clear charters, cadence, and outcomes. Support Medicaid Proposals management process by preparing strategic business reviews, facilitating discussions, and capturing decisions and actions. Lead annual and multi‑year strategic planning cycles, including development of strategic pillars, and prioritized initiatives. Partner with business leaders to articulate strategic intent, value propositions, growth opportunities, and competitive positioning. Translate high‑level strategy into actionable roadmaps, milestones, and dependencies across teams. Partner with senior leaders to translate strategic objectives into measurable goals, KPIs, and execution plans. Ensure financial, regulatory, and operational considerations are incorporated into governance decisions. Standardize ways of working to reduce ambiguity, rework, and misalignment across cross‑functional teams. Guides junior colleagues through consultation and mentoring in techniques and processes and provides functional (matrix) supervision.

Required Qualifications

• A minimum of 10 years of experience working in a highly regulated healthcare environment.
• A minimum of 3 years of relevant experience in Strategic Business Planning and/or Project Management Office (PMO) functions.
• Strong analytical capabilities, with a proven ability to synthesize complex information into clear, actionable strategic insights.
• Extensive experience partnering with senior executives and leading cross‑functional planning initiatives.
• Demonstrated success in developing executive‑level presentations and dashboards for senior leadership audiences.
• Direct experience with Aetna/CVS Health management and governance processes.

Preferred Qualifications

• Strong visual design, data visualization and storytelling skills.
• Demonstrates strong proficiency with Microsoft Office tools to build systems and collaborative environments that drive productivity.
• Mastery of problem solving and decision‑making skills
• Mastery of growth mindset (agility and developing yourself and others) skills.

Education

Bachelor's degree preferred or a combination of education and work experience.

Travel

Ability to travel up to 25% as business needs require.

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.

Benefits

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 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.

Equal Opportunity Statement

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

Application Deadline

We anticipate the application window for this opening will close on: 11/14/2026

Our Work Experience

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.