Medicaid Proposal Director

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.

Serving as the central leader for proposal activity, the Proposal Director advances established processes, applies tools and best practices, and ensures delivery of a high-quality final product. This leader proactively identifies challenges, mitigates risk, and communicates with clarity to keep stakeholders aligned, informed, and focused on critical deadlines. The role requires strong judgment, executive presence, and the ability to lead through ambiguity while balancing strategic positioning, proposal quality, and submission readiness.

Primary Responsibilities

• Direct the proposal workplan to ensure full alignment with project requirements, deliverables, and compliance expectations.
• Analyze RFPs, attachments, and amendments to identify and capture all direct, derived, and implied requirements.
• Lead the end-to-end proposal development process through final submission, ensuring quality, alignment, and on-time delivery.
• Plan, schedule, and facilitate color team reviews to strengthen quality, alignment, and overall proposal readiness.
• Influence cross-functional stakeholders and senior leaders to drive alignment, resolve issues, and secure timely decisions across the proposal lifecycle.
• Establish standards, define processes, and equip team members with the guidance and training needed to execute their roles effectively.
• Develop and enforce proposal timelines and schedules, ensuring disciplined execution and strict adherence to deadlines.
• Tailor proposal calendars and processes to each RFP while preserving process integrity and proactively addressing stakeholder needs and potential risks.
• Translate complex procurement requirements into clear priorities and expectations for cross-functional teams and proposal contributors.
• Lead multiple concurrent activities and stakeholders in a highly matrixed environment, maintaining momentum across competing priorities and compressed timelines.

• 8+ years of experience leading Medicaid managed care or healthcare proposal efforts.
• 5+ years of experience managing complex projects and driving the accurate completion of all requirements.
• Strong knowledge of Medicaid subcontractor and diverse supplier requirements.
• Excellent written and verbal communication skills.
• Demonstrated ability to work independently and deliver high-quality results that meet internal and external customer expectations under tight deadlines.
• Strong collaboration skills and the ability to work effectively across cross-functional teams.
• Demonstrated ability to influence in a matrixed environment without direct authority.
• Strong judgment and ability to synthesize complex requirements into clear priorities, action plans, and stakeholder decisions.
• Ability to adapt to rapidly changing priorities and develop creative, effective solutions.
• Flexibility to work evenings and weekends as proposal schedules require.
• Proficiency in Microsoft Word, Excel, PowerPoint, and SharePoint.

• Experience leading complex proposal efforts for high-value opportunities exceeding $1B.
• 8–10 years of experience in state government proposal development strongly preferred.
• APMP certification preferred.
• Strong analytical and critical thinking skills.
• Ability to perform effectively in demanding, deadline-driven environments.

• Bachelor’s degree or equivalent work experience

Pay Range

The typical pay range for this role is:

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.

Additional details about available benefits are provided during the application process and on Benefits Moments.

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