Lead Director, Business Enablement & Delivery

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. Job Overivew: Oak Street Health®, a part of CVS Health, helps older adults stay healthier and live fuller lives through our 230 centers across 27 states. Our value-based care model helps us consistently deliver better patient experiences and outcomes. As a Lead Director, you will play a critical role in supporting our Oak Street Health patients, providers and business by helping Oak Street Health turn strategic priorities into effective workflows, coordinated execution, and measurable business impact. This role is ideal for someone who thrives in complex, matrixed environments and knows how to connect business goals, operational design, and technology delivery to solve meaningful problems on a scale. This leader will play a central role in Oak Street Health’s business enablement model, working closely with business domain leaders, DDAT, Clinical Informatics, and field partners to improve workflows, support execution, and ensure strategic initiatives are translated into practical, operationally sound solutions. A key part of the role will be leading within a 5-in-the-box operating model, helping shape how work moves from business problem definition to workflow design, execution, field readiness, and sustained adoption. This leader will serve as a primary business-side partner in solving cross-domain problems, coordinating delivery, and making sure system-enabled initiatives drive real value for the business. Primary Job Duties & Responsibilities: Lead business enablement efforts across strategic initiatives, partnering with business, operations, DDAT, and Clinical Informatics teams to translate priorities into executable work Serve as a key business-side leader in the 5-in-the-box model, helping define problems, shape workflows, align stakeholders, and support coordinated execution Drive workflow design and operational process refinement, ensuring solutions account for upstream and downstream impacts across teams and functions Support cross-domain orchestration of major initiatives, helping sequence work, clarify ownership, and keep execution aligned to intended business outcomes Partner with Training, Change Management, and Field leaders to strengthen readiness, usability, adoption, and value realization Lead, coach, and develop managers and team members, building a culture of accountability, practical problem-solving, and collaboration Required qualifications 10+ years of leadership experience in healthcare, operations, technology, or value-based care environments Strong experience leading complex, cross-functional initiatives in matrixed organizations Demonstrated ability to translate business priorities into workflow, process, and operational execution Experience partnering closely with business, operations, technology, informatics, and delivery teams Experience working with system-enabled operational change, including workflow design, implementation, and adoption Ability to influence across stakeholders, align priorities, and drive execution in ambiguous environments Preferred Qualifications: The knowledge, skills, and abilities (KSAs) which are “nice to haves” in a candidate. HRBPs and leaders can use preferred skills to further screen candidates in the recruitment process. Experience in value-based primary care Experience with Epic-enabled workflows and clinical or operational process design Experience supporting large-scale business transformation, digital enablement, or operational improvement efforts Experience working across business and shared-service technology teams to drive execution and value realization Bachelor’s degree preferred Oak Street Health is on a mission to “Rebuild healthcare as it should be'', providing personalized primary care for older adults on Medicare, with the goal of keeping patients healthy and living life to the fullest. Our innovative care model is centered right in our patient’s communities, and focused on the quality of care over volume of services. We’re an organization on the move! With over 230 locations and an ambitious growth trajectory, Oak Street Health is attracting and cultivating team members who embody “Oaky” values and passion for our mission. Oak Street Health Benefits: Mission-focused career impacting change and measurably improving health outcomes for medicare patients Paid vacation, sick time, and investment/retirement 401K match options Health insurance, vision, and dental benefits Opportunities for leadership development and continuing education stipends New centers and flexible work environments Opportunities for high levels of responsibility and rapid advancement Oak Street Health is an equal opportunity employer. We embrace diversity and encourage all interested readers to apply. 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 offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families. This full‑time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well‑being of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility. Additional details about available benefits are provided during the application process and on Benefits Moments . We anticipate the application window for this opening will close on: 10/30/2026 Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.