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 (aut