The work we do for underserved senior communities is genuinely life-changing and keeps me coming back to the clinic.

A value-based primary care network for Medicare-eligible older adults, recently acquired by CVS Health for $10.6 billion, focusing on high-need geriatric populations.
Strong, distinctive culture identity
The Machine
Mike Pykosz
Co-founder & Former CEO
Oak Street Health is a healthcare company with 1,000+ employees headquartered in Chicago, IL, founded in 2012. A noble mission caught in a high-pressure metric engine.
Innovation
Oak Street Health takes a balanced approach to innovation with a score of 60/100.
Hierarchy
Oak Street Health leans toward structured & clear with a score of 80/100.
Collaboration
Oak Street Health leans toward team-oriented with a score of 75/100.
Work-Life Balance
Oak Street Health leans toward always-on hustle with a score of 20/100.
Mission
Oak Street Health leans toward purpose-driven with a score of 85/100.
Growth
Oak Street Health leans toward stable & steady with a score of 30/100.
Creagh Milford
President
Appointed in 2025 to lead the division's business strategy and manage the CVS integration and organizational rightsizing.
Mike Pykosz
Co-founder & Former CEO
Built the foundational value-based model and pushed employees hard via an 'impact equation' before departing post-acquisition.
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The work we do for underserved senior communities is genuinely life-changing and keeps me coming back to the clinic.
I am forced to take home 4 to 5 hours of charting and documentation every single night just to keep up.
There is constant, overwhelming pressure to upcode and over-diagnose to satisfy Medicare reimbursement metrics.
Leadership relies heavily on micromanagement and metrics, making it feel more like a corporate retail store than a healthcare clinic.
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