Lead Director, Proposal Writing

CVS Health•Work At Home-Illinois, IL

1d•$100,000 - $231,540•Remote

About The Position

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.

Requirements

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.
Bachelor’s degree or equivalent work experience

Nice To Haves

APMP or Shipley certification preferred.

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.