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Executive Director, Oak Street Health Regional Leader - Illinois at CVS Health, Field-Illinois (Chicago)

Executive Director, Oak Street Health Regional Leader - Illinois at CVS Health in Field-Illinois (Chicago). Full-time. $131,500 to $303,195 a year. Apply with swipeandhired.

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.

Oak Street Health , a CVS Health company, is committed to delivering high-quality care to older adults on Medicare, particularly in underserved communities. We focus on the kind of healthcare you'd want for your own family—personalized, accessible, and effective. Our mission is to rebuild healthcare around wellness and positive outcomes, not volume. Through dedicated care teams, we take the time to understand each patient and provide the support they need to live healthier, fuller lives. We emphasize value-based care, especially full-risk/capitated models, and leverage care management strategies to improve clinical and financial outcomes.

Oak Street Health is seeking to hire two Regional Vice Presidents (RVPs) in Illinois. One RVP will lead our North Region, while the second will oversee our Northwest Region . As the senior operational leader for their respective markets, each Executive Director/RVP will be responsible for driving performance across multiple centers, leading a cross-functional team, and ensuring exceptional patient, clinical, operational, and financial outcomes. Success in this role requires a highly visible, hands-on leadership approach, with regular time spent in health centers building relationships, supporting teams, and driving performance at the local level.

Key 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.

Consistently 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 leader in the community, cultivating relationships with key stakeholders and organizations.

Partner with your Senior Medical Director (dyad partner) to foster a collaborative, high-performing team environment focused on delivering exceptional patient care.

Work with the Treehouse (Oak Street Health’s Shared Services) to develop and execute on Oak Street Health’s top strategic priorities.

Share best practices and collaborate with peers across markets to drive enterprise-wide success.

Embody and promote Oak Street Health’s mission-driven, patient-first culture.

Qualifications
The candidate will have a strong work ethic, be a self-starter, and be able to be highly productive in a dynamic, collaborative environment. This position offers broad exposure to all aspects of the company’s business, as well as significant interaction with all the business leaders. The candidate will be expected to have the following key attributes:

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 with 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 with a passion for continuous improvement.

Willing to travel regularly to all clinic locations throughout Illinois.

Must reside in/near Chicago.

80% travel expected (4 days per week to the site locations).

Education
Bachelor's degree or equivalent

Anticipated Weekly Hours
40

Time Type
Full time

Pay Range
The typical pay range for this role is:

$131,500.00 - $303,195.00
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.

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: 11/20/2026

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.