Meet Dr. Toyin Ajayi: Healthcare Entrepreneur Responsible For Transforming Cityblock Health Into $6 billion Unicorn

Dr. Toyin Ajayi, physician and healthcare entrepreneur, co-founded and acts as the CEO of Cityblock Health, a New York–based, tech‑enabled provider. This provider specializes in integrated primary care, behavioral health, and social services across multiple US states. She has helped transform the company from a modest startup cut from Google’s Sidewalk Labs in 2017. It is now a “unicorn” valued at around $6 billion.

Solid African Roots

Dr. Toyin Ajayi was born in Boston to Nigerian parents and raised in Nairobi, Kenya. She would go on to earn a B.S. in Human Biology from Stanford University, an MPhil from the University of Cambridge, and an M.D. from King’s College London. She completed her residency at Boston Medical Center.

Cityblock Journey

Before joining Cityblock, she worked at Boston Medical Center as a family medicine hospitalist and held senior clinical roles including as Chief Medical Officer at Commonwealth Care Alliance where she managed care delivery for high‑needs Medicaid and Medicare individuals.

Dr. Ajayi became Cityblock’s President at its founding in 2017. She took over as CEO in March 2022 after her co‑founder stepped down. She has guided the company through rapid scaling and funding rounds totaling nearly $900 million. Her efforts have aimed to ramp up profitability and payer integration. She even oversaw a strategic restructuring by reducing 12% of the workforce. Meanwhile, she reinforced tech‑driven care models.

Cityblock’s unique model agencies a fixed per-member-per-month payment from Medicaid managed-care organizations and shares in cost savings when utilization falls aligning with its mission to drive equity through value-based care. It invests upstream in highly personalized, prevention-oriented health and social care to ultimately drive down costs and improve outcomes.

Central to her leadership is a focus on building trust and continuity in communities underserved by traditional healthcare. She uses her data‑driven system to try to eliminate the dangers posed by repeating one’s medical history. This repetition is regarded as harmful to therapeutic relationships.

Widespread Recognition

Dr. Ajayi has been recognised by numerous organisations for her work. She has been included in Time’s TIME100 Next, Modern Healthcare’s Women to Watch 2023, STAT’s STATUS List, and Aspen Institute’s Henry Crown Fellowship.