Lead Director, Proposal Writing

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. The role leads proposal‑writing strategy, translates capture insights into compelling narratives, and builds scalable processes that improve quality, efficiency and win rates. The leader partners across business development, product, legal and proposal operations to ensure strong alignment and execution across complex, high‑stakes procurements.

• 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 and motivate 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.

• 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 with SMEs, writers and production team.
• Ability to adapt to rapidly changing priorities through the identification and execution of creative solutions.
• Ability to work nights and weekends during active proposal development time frames as necessary to meet deadlines; up to 15‑30% travel may be required.
• Bachelor’s degree or equivalent work experience.
• APMP or Shipley certification preferred.

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

The typical pay range for this role is: $ – $. This range represents the base hourly rate or base annual full‑time salary for all positions within this job grade. The actual base salary offer will depend on experience, education, geography and other relevant factors. The position is eligible for a CVS Health bonus, commission or short‑term incentive program in addition to the base pay.

It also includes an award target in the company’s equity award program.

This full‑time position is eligible for a comprehensive benefits package designed to support the physical, emotional and financial well‑being of employees and their families. The benefits include medical, dental and vision coverage, paid time off, retirement savings options, wellness programs and other resources, based on eligibility. Additional details about 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.