Medicaid Proposal Director

CVS Health•Work At Home-Minnesota, MN

7d•$100,000 - $231,540

About The Position

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 At Aetna®, part of CVS Health, we proudly serve more than 26 million medical members through our broad range of health plan offerings. We're committed to delivering a simpler, more meaningful, and personal health care experience to each of them. As a Medicaid Proposal Director (a strategic, high-visibility leader) you will play a critical role by leading end-to-end proposal development for Medicaid procurements and re-procurements. In close partnership with senior leaders and key contributors, this role helps shape proposal strategy, align teams around shared priorities, and drive disciplined execution from kickoff through submission. The Proposal Director mobilizes cross-functional teams and external partners to deliver submissions that are accurate, complete, compliant, and compelling. This role operates with significant autonomy and influence, guiding complex, high-value pursuits, surfacing key risks and decision points, and driving alignment across business, operational, clinical, compliance, legal, and partner teams. 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.

Requirements

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.

Nice To Haves

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.

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.