Executive Director, Patient Engagement & Retention - Oak Street Health

At CVS Health, we’re building a world of health around every consumer and surrounding ourselves with dedicated colleagues who are passionate about transforming health care.

As the nation’s leading health solutions company, we reach millions of Americans through our local presence, digital channels and more than 300,000 purpose-driven colleagues – caring for people where, when and how they choose in a way that is uniquely more connected, more convenient and more compassionate. And we do it all with heart, each and every day.

Role Overview

Oak Street Health is seeking a strategic and operational leader to drive enterprise-wide patient retention and engagement efforts. The Executive Director will lead the development and execution of data-driven strategies, oversee a 150+ member Patient Engagement & Escalation Program (PEEP), and collaborate cross-functionally to improve patient outcomes and experience. Reports to the Associate VP, Patient Engagement & Retention.

Key Responsibilities

• Strategic Leadership:
• Develop and implement enterprise strategies to improve patient retention, engagement, and Wellness Review Visit (WRV) completion.
• Team Oversight:
• Lead and manage the PEEP team (150+ FTEs), including workforce planning, performance management, and professional development.
• Data & Analytics:
• Monitor program performance using analytics; identify improvement opportunities and implement solutions.
• Cross-Functional Collaboration:
• Partner with PMO, Clinical Ops, Learning, Membership, PRM, Population Health, and Med Cost teams to execute initiatives and manage change.
• Executive Communication:
• Serve as the enterprise retention lead, presenting insights and strategies to senior leadership and stakeholders.
• Budget Management:
• Oversee budgets for PEEP and related initiatives, ensuring efficient resource allocation.

Required 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:

• 15+ years in strategy, planning, or operations, including 4+ years in healthcare leadership.
• 4+ years managing direct reports, with experience leading large teams.
• Proven success in leading enterprise-wide initiatives with measurable impact.
• Strong analytical skills and ability to translate data into actionable strategies.
• Executive presence and experience presenting to senior leaders and boards.
• Excellent communication and stakeholder engagement skills.
• Ability to travel 5–10%.
• Master’s degree (MBA, MHA, MPH, MPP).
• Experience in value-based care and healthcare operations.
• 2+ years leading teams of 20+ members.
• Proficiency in Microsoft Office Suite (Excel, PowerPoint).
• Healthcare-specific operational leadership experience.
• What It Means to Be an “Oaky”

Preferred Qualifications

• Radiate Positive Energy

• Assume Good Intentions

• Drive Clinical Excellence

• Be Relentlessly Determined

• Create unmatched patient experiences
• Take ownership and deliver results
• Why Oak Street Health?

Oak Street Health is transforming healthcare for older adults on Medicare by delivering personalized, community-based primary care focused on quality over volume. With over 150 locations and growing, we’re building a team of passionate professionals who live our mission and values.

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.  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 our comprehensive and competitive mix of pay and benefits – investing in the physical, emotional and financial wellness of our colleagues and their families to help them be the healthiest they can be. In addition to our competitive wages, our great benefits include:

• Affordable medical plan options, a 401(k) plan (including matching company contributions), and an employee stock purchase plan.
• No-cost programs for all colleagues including wellness screenings, tobacco cessation and weight management programs, confidential counseling and financial coaching.
• Benefit solutions that address the different needs and preferences of our colleagues including paid time off, flexible work schedules, family leave, dependent care resources, colleague assistance programs, tuition assistance, retiree medical access and many other benefits depending on eligibility.

For more information, visit https://jobs.cvshealth.com/us/en/benefits

We anticipate the application window for this opening will close on: 10/24/2025

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