Lead Director - Service Operations - Strategy and Transformation

CVS Health • Chicago, IL

4d • Remote

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. Company: Oak Street Health Title: Lead Director - Service Operations - Strategy and Transformation Location: Remote Role Description: The Lead Director, Service Operations Strategy & Transformation will lead technology-driven process improvements across key Service Operations teams, including Patient Services, Pharmacy Tech, Triage Nurse, Referrals, and Medical Records. This role focuses on driving efficiency and enhancing patient experience through technology adoption and operational transformation. Partnering closely with Product, IT, Clinical Informatics, and Service Ops leadership, the Lead Director will design and implement solutions that deliver measurable impact. This position reports to the Executive Director, Service Operations.

Requirements

• 10+ years of leadership experience in shared services or healthcare operations
• Proven track record in cultural and operational transformation, including structured change management (stakeholder alignment, training, communications, outcome measurement)
• Successful leadership of vendor selection and large-scale technology deployments (impacting 100+ FTEs)
• Demonstrated ability to automate high-volume administrative processes
• Strong understanding of enabling technologies for service operations (automation, AI, self-service, agent assist)
• Exceptional strategic thinking, project management, and executive communication skills
• Highly collaborative, analytical, and adaptable in a fast-paced environment
• Self-starter with strong initiative, follow-through, and problem-solving capability
• Travel - up to 20%
• U.S. work authorization.
• Someone who embodies being “Oaky”

Nice To Haves

• Strong healthcare operations background
• Consulting experience with strategic and operational initiatives
• Proven ability to lead operations and technology projects
• Technical background (preferred but not required)
• Experience leading technology implementation end-to-end
• Demonstrated success in implementing major change for large-scale operations
• Ability to own problem-solving, including identifying issues, designing solutions, selecting appropriate technology, and driving implementation

Responsibilities

• Lead large-scale operational and technology transformation initiatives, driving efficiency and process improvements across healthcare operations.
• Own end-to-end solution design and implementation, including identifying business problems, selecting enabling technologies, and ensuring successful deployment.
• Manage cross-functional projects that integrate operations and technology, collaborating with internal teams and external partners to achieve strategic goals.
• Drive change management for major organizational shifts, ensuring adoption of new processes and technologies across large teams and complex environments.
• Provide strategic consulting and thought leadership, leveraging healthcare operations expertise to influence decisions and deliver measurable impact.

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

What This Job Offers

• Job Type: Full-time
• Career Level: Director