Associate, Strategy and Expansion

Development Programs Chicago, Illinois United States


Company: Oak Street Health 

Title: Associate, Strategy & Expansion

Location: 30 W. Monroe, Chicago IL or Remote 

Company Description

Oak Street Health believes everyone deserves great healthcare – the kind you’d want for your own family. We specialize in providing exceptional care for older adults on Medicare, often in underserved communities where there is little or no quality healthcare.

Oak Street Health is on a mission to rebuild healthcare as it should be with an innovative care model that centers on wellness-based, positive health outcomes for patients, not the volume of services provided. Our unwavering commitment to keeping patients healthy is highlighted by dedicated care teams that take time to get to know each individual, providing the personalized care they need to stay healthy and live life more fully. 

We’re an organization on the move! Our rapidly growing national network of primary care centers is staffed by a diverse team of outstanding care providers, service team members, technologists, community outreach experts, business professionals, and more. For more information, visit

Role Description:

The Associate, Strategy and Expansion will be a part of Oak Street’s Strategy, Corporate Development, and Expansion team, reporting into the Vice President, Strategy and Corporate Development and interacting with leaders and teams across Oak Street. This individual will support problem-solving, own analytics, assist in making recommendations, and support new program development for key strategic initiatives at Oak Street. 

While focus areas may vary over time, based on the organization’s top priorities, key focus areas for 2023 are:

  • Oak Street Health PACE: Oak Street Health received the award from the State of IL to serve individuals via the Program for All-Inclusive Care for the Elderly (PACE). The Associate, Strategy and Corporate Development will assist in analysis, program development, and project management to ready Oak Street for a 2024 program launch.

  • Expansion: Oak Street Health continues to expand its footprint across the U.S. The Associate, Strategy and Corporate Development will assist in market analysis and prioritization to support Oak Street’s continued growth.

  • Other strategic initiatives, as prioritized by senior leadership

This role will serve as an ideal starting point for exceptional analytical and business talent to enter a proven, high-growth organization at the cutting edge of healthcare innovation.  The Associate, Strategy and Expansion will have the opportunity to own and drive mission-critical projects while also developing their professional skillset, working with Oak Street leadership, gaining cross-functional experience, and learning the Oak Street business model.

The ideal candidate will have strong relationship skills, be self-directed, and enjoy working with a team in a fast-paced environment, while bringing their experience, leadership, and innovative ideas. The role will be fluid, evolving based on organizational priorities and the professional development of the Associate.


Core Responsibilities:

Spanning both internal strategic priorities and external affairs, you will:

  • Conduct financial and operational analysis to inform and help prioritize the organizational agenda

  • Work closely with the VP Strategy and Corporate Development, Chief Innovation Officer, and Chief Financial Officer to structure, analyze, and execute against high-priority strategic initiatives across the organization

  • Manage cross-functional development and execution of select initiatives

  • Support preparation of executive-level presentations for our senior leadership team

  • Support program design and development in the lead-up to launch of the Oak Street Health PACE program

  • Support Oak Street Health expansion efforts, including conducting critical analysis to prioritize geographies for growth

  • Other duties as assigned. 


What are we looking for?

  • High level of organization and detail orientation

  • Experience collaborating on projects across multiple departments

  • Proficient with Microsoft Excel or other standard analysis tools (SQL, Alteryx, etc.), with an interest in / aptitude for data-driven analysis 

  • Strong intellectual curiosity and problem-solving ability

  • Ability to navigate leadership and operational complexities

  • Passion for excellence, willing to go the extra mile to achieve objectives and ensure consistently high quality work product

  • Quick learner comfortable with ambiguity

  • Strong accountability and discipline against timelines and deliverables

  • Collaborative working style, able to work cross functionally

  • Bachelor’s degree required 

  • US work authorization

  • Someone who embodies being “Oaky”.

What does being “Oaky” look like?

  • Radiating positive energy

  • Assuming good intentions

  • Creating an unmatched patient experience

  • Driving clinical excellence

  • Taking ownership and delivering results

  • Being relentlessly determined


Oak Street Health Benefits: 

  • Mission-focused career impacting change and measurably improving health outcomes for Medicare patients

  • Paid vacation, sick time, and investment/retirement 401K match options

  • Health insurance, vision, and dental benefits

  • Opportunities for leadership development and continuing education stipends

  • New centers and flexible work environments

  • Opportunities for high levels of responsibility and rapid advancement


Oak Street Health is an equal opportunity employer. We embrace diversity and encourage all interested readers to apply. 

Learn more at