Executive Director, Strategic Operations

CVS Health•Chicago, IL

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. The Executive Director, Strategic Operations is a relationship‑driven senior leader accountable for defining, prioritizing, and advancing the clinical and operational capabilities roadmap for a technology‑enabled, value‑based primary care organization. This role is ideal for a leader who thrives in complex, matrixed environments and excels at connecting people, priorities, and processes to drive disciplined execution. Partnering closely with Technology, Data & Analytics (DDAT), Clinical Informatics, and business leadership, this executive translates strategy into real‑world impact—ensuring that business priorities, technology investments, and clinical workflows are tightly aligned to deliver clinical excellence, operational efficiency, and improved value‑based care performance. This leader will establish and operate a centralized, business‑led function that serves as the primary integrator across clinical operations, technology delivery, and enterprise governance. The role owns the enterprise clinical workflow blueprint, sets priorities for business demand and investment decisions, and maintains the delivery roadmap for business‑led initiatives across existing systems and platforms, including EHR optimization and the identification, scaling, and value realization of AI and automation solutions. As a trusted partner to senior leaders, the Executive Director ensures that strategic investments translate into scalable, sustainable capabilities that support Oak Street Health’s growth and performance goals.

Requirements

10+ years of senior leadership experience in large‑scale healthcare environments, with deep exposure to Value‑Based Care models.
Extensive experience within Epic ecosystems, with a strong understanding of how system design shapes clinical operations and documentation.
Clinical, healthcare operations, or health technology background preferred, ensuring workflows are grounded in frontline clinical reality.
Demonstrated success leading complex, multi‑site, cross‑functional business implementations and centralizing previously distributed functions.
Proven ability to operate effectively within shared‑service and matrixed environments while maintaining strong business ownership of priorities and roadmaps.
Experience applying AI and automation strategically to solve meaningful business and clinical challenges in healthcare.

Responsibilities

Establish and lead enterprise governance that aligns clinical and operational capability needs with technology delivery.
Define clear decision rights, prioritization frameworks, and engagement models across OSH business leaders and DDAT partners to guide investment decisions and execution.
Translate strategy into clear business problems, outcomes, and success measures.
Partner with Technology and EHR teams to shape scalable capabilities, coordinate upstream/downstream impacts, and ensure solutions deliver intended clinical, financial, and operational results.
Establish and govern enterprise clinical and operational workflows, creating a centralized and trusted source of truth.
Drive alignment and consensus across OSH leaders while managing upstream and downstream process impacts across the organization.
Act as a key business‑side Epic subject matter expert, serving as the liaison between business, technology, and engineering teams.
Ensure system implementations translate into efficient, modern, and scalable workflows within clinical centers.
Serve as the senior business sponsor for system‑enabled initiatives, ensuring approved priorities remain aligned to business outcomes.
Run structured intake, triage, and prioritization aligned to enterprise goals and capacity.
Surface risks, tradeoffs, and dependencies early, enabling timely leadership decisions and predictable execution.
Own the health of the business delivery and implementation portfolio by instilling strong program management discipline, monitoring execution risk, and escalating material issues and opportunities to senior leadership.
Champion field readiness, usability, and sustained adoption by partnering with Training, Change Management, and Field Leadership to translate system initiatives into measurable operational and clinical impact.
Lead the business strategy for AI and automation by identifying high‑impact use cases and ensuring initiatives deliver measurable clinical, operational, and financial value.
Collaborate with Finance and OSH leadership to manage business‑side capability planning and funding, ensuring investments align with long‑term strategic growth and value‑based care objectives.
Build, lead, and develop a high‑performing team of business operations and delivery leaders, fostering a culture of accountability, collaboration, and results.