Role SummaryThis role sits at the intersection of finance, operations, growth, and payer partnerships. The Executive Director will create the financial infrastructure needed to understand performance at every center, strengthen payer financial administration, and support better decisions on where and how Oak Street Health grows. The successful candidate will bring deep financial discipline, strong operational judgment, and the ability to translate complex data into practical actions for field and executive leaders.
Key Responsibilities1. Center Economics & Field Finance Leadership- Establish and maintain a comprehensive center-level economics framework across Oak Street Health's national portfolio of 230+ centers.
- Develop financial reporting, analytics, and performance management routines that create clear visibility into center-level financials and business drivers.
- Partner closely with Division Presidents, Regional Vice Presidents, center leadership, and operations teams to drive financial accountability and operational rigor.
- Identify overperforming and underperforming centers, diagnose root causes, and translate findings into practical improvement initiatives.
- Support center-level financial transparency by creating standardized views of revenue, cost, productivity, contribution margin, and key operating metrics.
- Build business cases for operational initiatives that improve productivity, efficiency, quality of execution, and financial performance.
- Provide executive-ready insights that connect operational performance, patient growth, center economics, and long-term profitability.
- Partner with Growth and Development teams to evaluate market opportunities and inform where Oak Street Health should open new centers.
2. Health Plan Finance Leadership- Lead the Health Plan Finance team responsible for financial administration of payer contracts and risk-based arrangements.
- Oversee monthly reconciliation of claims activity, account statements, cash receipts, and payer settlement reporting.
- Manage membership calculations, attribution validation, and related financial processes across payer partners.
- Oversee revenue and RAF accruals, data validation, and analysis supporting value-based care financial performance.
- Support month-end close, quarterly reviews, and annual financial processes in partnership with Accounting and FP&A.
- Support risk contract finances, including financial statement reconciliations, cash receipt validation, settlement tracking, claims-to-statement analysis, and issue resolution.
- Partner with payer organizations and internal contracting teams to resolve financial discrepancies and improve reporting transparency.
- Develop scalable controls, processes, and reporting routines that support continued growth and payer complexity.
3. Strategic Leadership & Business Partnership- Serve as a trusted advisor to Oak Street Health Finance and Operating Leadership on center economics, health plan financial performance, and growth decisions.
- Bring an enterprise mindset to finance leadership, connecting field operations, payer economics, growth strategy, and financial outcomes.
- Lead, mentor, and develop a high-performing team across Center Economics, Field Finance, and Health Plan Finance.
- Drive a culture of accountability, continuous improvement, operational excellence, and fact-based decision-making.
- Identify opportunities to leverage analytics, automation, and process improvement to enhance insight quality and team efficiency.
- Support executive presentations, leadership reviews, Board materials, and strategic planning discussions as needed.
Required Qualifications- Bachelor's degree in Finance, Accounting, Economics, Business, or a related field.
- 15+ years of progressive finance leadership experience, preferably in healthcare, payer, provider, value-based care, or risk-bearing organizations.
- Demonstrated experience leading financial planning, operational finance, business performance management, or multi-site financial analytics.
- Strong understanding of healthcare economics, payer contracts, revenue recognition, risk-based reimbursement, and operational finance.
- Experience partnering directly with senior operational leaders and executive stakeholders.
- Advanced financial modeling, analytical, problem-solving, and executive presentation skills.
- Proven ability to lead and develop high-performing finance teams.
Preferred Qualifications- MBA, CPA, or other advanced degree or professional certification.
- Experience in value-based care, Medicare Advantage, population health, or provider risk arrangements.
- Experience managing center, market, or unit-level economics in a multi-site healthcare environment.
- Familiarity with membership accounting, RAF, claims reconciliation, payer settlements, and risk contract administration.
- Experience supporting market development, network expansion, or growth investment decisions.
Pay RangeThe 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.
Great benefits for great peopleWe 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: 08/11/2026
