Lead Director, Strategic Planning, Proposals

CVS Health; Hartford (CT); On-site; USD 100,000 - 232,000; Full time

Benefits offered by this job

Medical coverage

Dental coverage

Vision coverage

Paid time off

Retirement options

Equity award program

Job summary

CVS Health is seeking a seasoned leader to design and maintain a Medicaid governance model, lead annual and multi-year strategic planning, and provide independent analysis to guide initiatives.

You will collaborate with senior executives, establish governance forums, translate strategy into actionable roadmaps, and ensure regulatory and financial considerations are reflected in decisions while mentoring teams.

Qualifications

• Minimum 10 years in a highly regulated healthcare environment.
• Minimum 3 years in Strategic Business Planning or PMO.
• Strong analytical capabilities to synthesize complex information into insights.
• Experience partnering with senior executives and leading cross‑functional planning.
• Experience presenting to executive leadership and dashboards.

Responsibilities

• Design and maintain a Medicaid governance model with clear roles and accountability.
• Facilitate governance forums with charters, cadence, and outcomes.
• Support Medicaid Proposals management with strategic reviews and decisions.
• Lead annual and multi-year strategic planning cycles and pillars.
• Articulate strategic intent, value propositions, and growth opportunities with leaders.
• Translate strategy into roadmaps, milestones, dependencies.
• Set measurable KPIs and execution plans with senior leaders.
• Incorporate financial, regulatory, and operational considerations into governance.
• Standardize ways of working to reduce ambiguity and misalignment.
• Mentor junior colleagues and provide matrix supervision.

Skills

Strategic planning

PMO experience

Executive presentations

Cross-functional leadership

Data visualization

Education

Bachelor's degree preferred

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

$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: 11/14/2026

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