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.

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.

• 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

• 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

• 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…