Lead Director, Proposal Writing

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:

This is a remote position that can sit anywhere in the United States.

The Director of Proposal Writing is a strategic leader responsible for delivering high-quality, competitive proposals that drive business growth. This role leads proposal writing strategy, translates capture insights into compelling narratives, and builds scalable processes that improve quality, efficiency, and win rates.

This leader partners across business development, product, legal, and proposal operations teams to ensure strong alignment and execution across complex, high-stakes procurements.

Core Responsibilities:

• Lead enterprise proposal writing strategy and align execution with capture priorities and business goals.
• Support the writers and lead any efforts in kick-off meetings, color team reviews, status meetings, and critical milestones throughout the entire proposal process as defined by the proposal timeline.
• Partner with cross-functional leaders to drive alignment, strengthen messaging, and improve competitive positioning.
• Build high-performing proposal teams, motivating and leading employees in a positive manner.
• Translate capture strategies into clear, persuasive proposal narratives that reflect organizational value.
• Establish and scale standardized processes, tools, and workflows to improve efficiency and consistency.
• Own proposal performance outcomes, including quality, timeliness, and continuous improvement across bids.
• Use data, metrics, and insights to evaluate performance and inform decision-making.
• Lead, coach, and develop a high-performing team of proposal writers.
• Manage capacity, resources, and timelines across multiple concurrent proposals to ensure delivery excellence.
• Identify and mitigate risks early by proactively addressing gaps in readiness, alignment, or execution.
• Champion innovation and adoption of tools, including AI-enabled solutions, to enhance proposal quality and efficiency.
• Empower individuals to problem-solve and identify innovative ways to streamline processes and procedures.
• Establish trusted relationships across teams and leadership levels, creating a culture of partnership, transparency, and accountability.
• Stay current in the latest approaches to responding to Medicaid procurements and healthcare industry topics.
• Learn and build expertise across Medicaid business.

Required Qualifications:

• 3+ years of experience leading, developing, and inspiring high-performing teams through effective coaching, mentorship, clear communication, and continuous feedback.
• 5+ years of experience creating compelling, audience-aware Medicaid proposal responses.
• 10+ years of proposal writing with Federal, Medicaid or Healthcare experience.
• Intermediate to advanced knowledge of Microsoft Office, including Word, PowerPoint and Excel.
• Exceptional communication, collaboration, delegation and organization skills
• Experience leading and guiding proposal strategies and meetings with key stakeholders.
• Strong team collaboration skills, including SMEs and other contributors, writing team, and production team.
• Ability to adapt to rapidly changing priorities through the identification and execution on creative solutions
• ​Ability to work nights and weekends during active proposal development timeframes as necessary to meet deadlines, up to 15-30% travel may be required.

Education:

• Bachelor’s degree or equivalent work experience
• APMP or Shipley certification preferred.

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.