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Olaoluwa Fayanju, MD MSc has a wide range of work experience. From 2003 to 2022, they have held multiple roles in various companies. Olaoluwa began their career as an Assistant Research Analyst at TIAA-CREF in 2003. In 2006, they became a Consultant at Simon Kucher & Partners. From 2012 to 2015, they were a Resident at Cook County Loyola Provident Family Medicine Residency and an Attending Physician, Regional Medical Director, Senior Medical Director, and Medical Director at Oak Street Health. In 2016, they were a Health System Clinician at Northwestern University - The Feinberg School of Medicine and a Clinical Assistant Professor at the University of Chicago - The Pritzker School of Medicine. In 2021, they became a Member of the Health Equity Roundtable at The White House. Most recently, they were appointed as the Chief Medical Officer at RubiconMD in 2022.

Olaoluwa Fayanju, MD MSc obtained a Doctor of Medicine (M.D.) from Tufts University School of Medicine in 2012. Olaoluwa then attended Harvard Business School in 2017, but did not receive a degree. From 2005 to 2007, they attended Harvard T.H. Chan School of Public Health and obtained an MS in Health Policy and Management. Lastly, they obtained a Bachelor of Arts (B.A.) in History from Harvard University from 1999 to 2003.