Senior Medical Director

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

Job Title: Senior Medical Director

Location: 8033 A W Florissant Ave, Jennings, MO 63136

Employment Type: Full-Time, Monday-Friday, 8am-5pm

Salary: $275,000 - $290,000

Role Description

The Senior Medical Director joins Oak Street Health at a transformative time for primary care, leading the market transition from fee-for-service to value-based care. Partnering directly with the Regional Vice President, this position drives operational and clinical excellence across hospital admissions, quality metrics, patient satisfaction, provider engagement, and medical expense management. To maintain a deep connection to patient care and clinic workflow, the Senior Medical Director practices primary care in health center clinics 2.5 days per week alongside provider colleagues. This role reports directly to the Executive Medical Director for the region and serves as a key clinical thought partner in refining the overall care model.

Core Responsibilities

• Medical Director Management & Coaching

• Supervise, mentor, and align health center Medical Directors with organizational priorities.

• Guide leaders through team management, performance feedback, and resolution of daily operational questions.

• Train medical directors on data-driven tools, quality dashboards, and initiatives to keep patients healthy and reduce avoidable hospitalizations.

• Instill managed care perspectives into leadership routines and explain provider performance/compensation structures.

• Lead the interviewing, hiring, onboarding, and retention of providers across the region.

• Physician Leadership Development

• Partner with Provider Services to cultivate an internal pipeline of skilled clinical leaders.

• Coach providers in problem-solving, communication, conflict resolution, value-based care delivery, and executive collaboration.

• Organizational Strategy & Clinical Programs

• Represent Oak Street Health to external partners (e.g., health plans, health systems) to build sustainable strategic partnerships.

• Serve on cross-functional committees to enhance the care model, including:

• Medical & Care Management

• Quality Improvement & Utilization Management

• Network & Health Plan Management

• Documentation & Risk Adjustment

• Clinical Compliance & Policy Development

• Population Health Leadership

• Supervise interdisciplinary Complex Care Teams serving high-need patient populations.

• Oversee Transitions Nurses monitoring hospitalized patients and coordinating post-discharge care.

• Collaborate with Population Health and Quality teams to innovate care delivery.

• Lead documentation and coding compliance, including provider education and chart reviews.

• Execute other clinical and operational duties as assigned.

Qualifications & Experience

• Education & Board Certification:

• M.D., D.O., or DNP degree.

• Physicians must be Board Certified in Internal Medicine or Family Medicine.

• DNPs must be certified in a primary care discipline.

• Preferred: Fellowship training in Geriatrics or advanced degrees (M.B.A., M.P.H., J.D.).

• Clinical Experience: Minimum of 5 years in an outpatient primary care setting.

• Leadership Experience: Minimum of 3 years as a Medical Director or clinical executive, directly managing a medical group of 20 or more providers.

• Domain Expertise:

• Demonstrated experience in managed care, value-based care models, and payer-provider alignment.

• Proven track record using metrics to analyze cost, quality, and patient satisfaction data to redesign clinical workflows.

• Strong familiarity with population health principles and efficient resource allocation.

• Work Authorization: Valid US work authorization required.

Cultural Alignment ("Being Oaky")

• Radiate positive energy and assume good intentions.

• Drive clinical excellence while creating an unmatched patient experience.

• Take personal ownership to deliver measurable results.

• Thrive in a fast-paced, scrappy, and innovative healthcare environment.

• Remain composed under pressure and navigate ambiguity with proactive problem-solving skills.

Why Oak Street Health?

Oak Street Health provides the opportunity to lead healthcare innovation on the front lines of value-based care, backed by a collaborative and supportive culture. Benefits include:

• Competitive salary and comprehensive health, dental, and vision coverage

• Paid time off (vacation and sick leave)

• Generous 401(k) match with immediate vesting

• Continuous professional and leadership development programs

Oak Street Health is an Equal Opportunity Employer.

Pay Range

The typical pay range for this role is:

$184,112.00 - $396,550.00

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: 09/28/2027

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

CVS Health is an equal opportunity/affirmative action employer, including Disability/Protected Veteran — committed to diversity in the workplace.