Executive Director, Oak Street Health Regional Leader - Illinois

CVS Health•Chicago, IL

2d•$131,500 - $303,195

About The Position

Oak Street Health, a CVS Health company, is hiring two Regional Vice Presidents in Illinois: one to lead the North Region and one to oversee the Northwest Region. Each Executive Director/Regional Vice President serves as the senior operational leader for their market, overseeing multiple centers and a cross-functional team while ensuring strong patient, clinical, operational, and financial outcomes. The role requires visible, hands-on leadership, including regular time in health centers to build relationships, support teams, and improve local performance. The position oversees approximately 6–8 clinics, holds full P&L responsibility, and advances Oak Street Health’s mission of delivering high-quality, personalized, accessible care to older adults on Medicare, particularly in underserved communities. The role partners with a Senior Medical Director and Oak Street Health’s Shared Services team, builds community and healthcare partnerships, and collaborates with peers across markets. Regular travel throughout Illinois is required, with 80% travel expected (four days per week at site locations). The candidate must reside in or near Chicago.

Requirements

10+ years of experience in healthcare provider operations, including leadership roles in physician group management, health plan operations, or clinic administration.
5+ years in leadership roles demonstrating operational excellence and strategic impact.
Proven track record of leading high-performing, cross-functional teams.
Knowledge of provider performance, retention strategies, and value-based contracting operations.
Strong business acumen, including experience managing P&L and driving growth.
Demonstrated ability to innovate and implement change in complex environments.
Exceptional communication, relationship-building, and leadership skills.
Growth mindset and passion for continuous improvement.
Willingness to travel regularly to clinic locations throughout Illinois; 80% travel is expected, or four days per week at site locations.
Must reside in or near Chicago.
Bachelor’s degree or equivalent.
Strong work ethic, self-starter, and ability to be highly productive in a dynamic, collaborative environment.

Responsibilities

Oversee day-to-day operations for approximately 6–8 clinics, ensuring high performance and alignment with Oak Street Health’s mission.
Own full P&L responsibility, driving profitability while maintaining high standards of care and service.
Exceed clinical quality metrics, patient acquisition goals, and financial targets.
Build strategic partnerships with local healthcare providers, health plans, insurance agencies, and community organizations to accelerate growth and improve outcomes.
Serve as a visible and trusted community leader and cultivate relationships with key stakeholders and organizations.
Partner with the Senior Medical Director to foster a collaborative, high-performing team focused on exceptional patient care.
Work with Treehouse, Oak Street Health’s Shared Services, to develop and execute strategic priorities.
Share best practices and collaborate with peers across markets to support enterprise-wide success.
Embody and promote Oak Street Health’s mission-driven, patient-first culture.
Travel regularly to clinic locations throughout Illinois.