Lead Director - Service Operations - Digital Transformation

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 Digital Transformation Location: Remote/Virtual Role Description: The Lead Director, Service Operations Digital Transformation will drive improvements in efficiency and patient experience across central Service Ops teams through technology enablement.

Role focus is on technology adoption and process transformation within five Service Operations teams: Patient Service contact center, Pharmacy Technician contact center, Triage Nurse contact center, Referrals processing, and Medical records requests.

Service Operations at Oak Street is the central administrative function supporting all clinics. Candidates must have proven experience leading large operations change initiatives that have quantifiable business impact (e.g. cost savings, FTE labor savings, improvement in KPIs like cycle time, etc…).

Examples of initiatives can be implementations of new vendor or home-grown technologies, changes in existing technologies, or significant changes in processes/workflows. This role partners closely with Product, IT, Clinical Informatics, Patient Experience, and Service Ops leaders to implement solutions that enhance efficiency and patient experience.

The role reports to the Executive Director, Service Ops. Strong communications skills are required for successful partnership with these teams (e.g. ability to clearly articulate/explain/frame business problems, solution rationale, and tradeoffs, and ability for executive-level storytelling using data).

Core Responsibilities: Optimize existing technology tools (e.g., Oak Street’s EHR, telephony) to drive measurable performance improvements. Identify and adopt new technologies, develop business cases, run vendor selection processes, and lead implementation.

Drive process automation through robotic process automation and AI-enabled solutions. Lead structured change management initiatives to ensure technology adoption, including communication, training, stakeholder engagement, and feedback measurement.

Shape Service Ops–wide technology strategy in partnership with CVS leadership, ensuring alignment to enterprise priorities while avoiding duplication of Business Ops Strategy scope. Own build/buy and vendor selection decisions for Service Ops technologies, in collaboration with enterprise stakeholders as appropriate.

Design scalable processes to support Service Ops growth and expansion. Manage a pipeline of prioritized technology initiatives and allocate resources to high-impact opportunities Maintain strong relationships with Service Ops leaders and support partners (training, workforce management, analytics, etc.).

Key Performance Indicators (KPIs) Achieve >20% per-member per-month cost efficiency savings within Service Ops over two years. Automate >30% of Service Ops administrative processes within two years. Attain >30% patient self-service rate for requests currently handled by call centers within two years.

What are we looking for? 10+ years in shared services (contact center or back office) or healthcare operations leadership. Proven experience leading cultural and operational transformation within large operational teams, including structured change management (stakeholder alignment, training, communications, outcome measurement).

Successful leadership of vendor selection and large-scale technology deployments (affecting >100 FTEs), especially for workflow automation tools and customer self-service tools like chatbots or voice agents. Demonstrated ability to automate high-volume administrative processes such as appointment scheduling or insurance processing.

Strong understanding of enabling technologies for service ops (automation, AI, self-service, agent assist). Commitment to Patient Service Principles: Demonstrates a strong focus on people by prioritizing patients and colleagues, acting with empathy, and fostering an inclusive, engaging environment.

Strives for innovation, collaboration, and simplicity in care delivery, while upholding integrity, safety, and quality in every interaction. Strong strategic thinking, project management, and executive communication skills. Collaborative, analytical, and adaptable in a fast-paced environment.

Bachelor’s degree or equivalent experience. Self-starter with a high degree of drive, initiative, and follow through Commitment to company vision A flexible and positive attitude High level of integrity Travel - up to 20% U.S. work authorization.

Someone who embodies being “Oaky” What does being “Oaky” look like? Radiating positive energy Assuming good intentions Creating an unmatched patient experience Driving clinical excellence Taking ownership and delivering results Being relentlessly determined Why Oak Street Health?

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 150 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. Learn more at www.oakstreethealth.com/diversity-equity-and-inclusion-at-oak-street-health 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: 12/31/2026 Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.