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At CVS Health, we’re building a world of health around every consumer and surrounding ourselves with dedicated colleagues who are passionate about transforming health care.

As the nation’s leading health solutions company, we reach millions of Americans through our local presence, digital channels and more than 300,000 purpose-driven colleagues – caring for people where, when and how they choose in a way that is uniquely more connected, more convenient and more compassionate. And we do it all with heart, each and every day.

Position Summary

The Director, Knowledge Enablement plays a critical role in enhancing the proposal development lifecycle through the strategic use of technology, data-driven insights, and staff development. This leader will oversee teams responsible for managing content platforms, implementing AI-driven solutions, developing and delivering training and onboarding programs, and developing reporting and analytics capabilities. They will also lead change management efforts to drive adoption of new tools and processes, ensure alignment with organizational priorities, and promote governance and standardization across proposal operations. The ideal candidate brings a forward-thinking, collaborative approach to knowledge management and enablement—ensuring proposal teams are equipped, informed, and empowered to succeed.

The right candidate for this role will demonstrate the following aptitudes:

+ Lead the integration and effective use of emerging technologies, including AI, to enhance content generation, analysis, and overall proposal efficiency.

+ Oversee the development and maintenance of dashboards and reporting tools that provide actionable insights into proposal metrics, content utilization, and team performance. Leverage data to inform strategy and drive continuous improvement.

+ Maintain a detail-oriented and process-driven mindset while remaining agile and responsive to shifting priorities and deadlines.

+ Exhibit intellectual curiosity and a proactive approach to identifying challenges and implementing effective, scalable solutions.

+ Build and sustain strong, trust-based relationships across all levels of the organization, fostering alignment and cross-functional collaboration.

+ Demonstrate a strong focus on operational efficiency, maximizing output and impact with thoughtful use of time, tools, and team resources.

+ Champion the upskilling of proposal team members through the design and delivery of thoughtful, role-specific training and onboarding programs that promote continuous learning and performance excellence.

+ Show flexibility and dedication by supporting proposal development efforts during high-demand periods, including evenings and weekends, as needed to meet critical deadlines.

Job Requirements:

+ Minimum of 8 years of progressive leadership experience in proposal management, content strategy, or training within the healthcare industry, with a deep understanding of regulatory and compliance-driven environments.

+ At least 3 years of hands-on experience with proposal automation, content management, or workflow tools, including demonstrated success in designing and implementing scalable solutions.

+ Proven experience leveraging AI-driven content tools and automation platforms to enhance proposal development, content analysis, and team efficiency.

+ Demonstrated ability to design and deliver impactful training and onboarding programs that upskill proposal teams and drive adoption of tools and best practices.

+ Proficiency in reporting and analytics platforms, with the ability to translate data into actionable insights and performance improvements.

+ Strong organizational and project management skills, with a track record of delivering high-quality outputs on time in fast-paced, deadline-driven environments.

+ Exceptional verbal and written communication skills, with the ability to synthesize complex information and present strategic recommendations to diverse audiences.

+ Naturally curious and self-motivated, with a problem-solving mindset and the ability to adapt quickly to shifting priorities and business needs.

+ Proven ability to build strong relationships and communicate effectively across all levels of the organization, including both technical and non-technical stakeholders.

+ Advanced proficiency in Microsoft Word, Excel, PowerPoint, and familiarity with proposal automation and content management technologies.

+ Willingness and ability to travel up to 25% to support proposal planning, stakeholder engagement, and strategic proposal activities.

Preferred Qualifications:

+ 5+ years of experience in a proposal environment, preferably within Medicaid Managed Care or other government-sponsored healthcare programs.

+ Proven ability to collaborate effectively across cross-functional teams, including Business Development, Compliance, IT, and subject matter experts.

+ Hands-on experience with AI-driven content tools and automation platforms, with a focus on improving proposal quality, efficiency, and scalability.

+ Association of Proposal Management Professionals (APMP) certification(s), such as Foundation, Practitioner, or Capture Practitioner.

+ Experience leading change management initiatives related to technology adoption, process improvement, or team enablement.

+ Familiarity with healthcare RFP requirements, including state-specific procurement processes and compliance standards.

+ Demonstrated success in building and scaling training programs that support proposal team development and tool adoption.

Education

+ Bachelor's degree preferred/specialized training/relevant professional qualification.

Pay Range

The typical pay range for this role is:

$100,000.00 - $231,540.00

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 our comprehensive and competitive mix of pay and benefits – investing in the physical, emotional and financial wellness of our colleagues and their families to help them be the healthiest they can be. In addition to our competitive wages, our great benefits include:

+ **Affordable medical plan options,** a **401(k) plan** (including matching company contributions), and an **employee stock purchase plan** .

+ **No-cost programs for all colleagues** including wellness screenings, tobacco cessation and weight management programs, confidential counseling and financial coaching.

+ **Benefit solutions that address the different needs and preferences of our colleagues** including paid time off, flexible work schedules, family leave, dependent care resources, colleague assistance programs, tuition assistance, retiree medical access and many other benefits depending on eligibility.

For more information, visit https://jobs.cvshealth.com/us/en/benefits

We anticipate the application window for this opening will close on: 11/01/2025

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

We are an equal opportunity and affirmative action employer. We do not discriminate in recruiting, hiring, promotion, or any other personnel action based on race, ethnicity, color, national origin, sex/gender, sexual orientation, gender identity or expression, religion, age, disability, protected veteran status, or any other characteristic protected by applicable federal, state, or local law.