Dr. Toyin Ajayi’s story is one of heritage, intellect and mission-driven leadership.
Born into a Nigerian family rooted in faith, discipline and community responsibility, she grew up watching her parents live out the belief that those with education carry an obligation to uplift those without access. That upbringing would later become a defining force in her work, shaping a passion to serve people whom society overlooks.
Her academic path reflects both ambition and purpose. After completing her undergraduate studies at Stanford University, she crossed the Atlantic to the University of Cambridge where she earned her master’s degree in Medical Sciences, immersing herself in research foundations that would later inform her approach to care innovation. She then attended King’s College London School of Medicine, where she earned her medical degree and achieved a Distinction in Clinical Practice, a marker of both excellence and the discipline often associated with Nigerians who excel in global academic spaces.
Her clinical journey continued in the United States at Boston University School of Medicine and Boston Medical Center, where she undertook her family medicine residency. Working in safety-net hospitals exposed her to the structural inequities of American healthcare, patients battling poverty, unstable housing and chronic disease, all within fragmented systems. Those experiences reinforced a truth she had absorbed in childhood: healthcare must not stop at treating illness, it must care for people.
Before venturing into
entrepreneurship, Dr. Ajayi took leadership roles that deepened her perspective. She served as Chief Medical Officer at Commonwealth Care Alliance in Massachusetts, designing programs for medically complex patients, and later worked at Sidewalk Labs, an Alphabet company exploring how cities and technology could improve human wellbeing.
That momentum culminated in 2017, when she co-founded Cityblock Health with fellow innovators Iyah Romm and Bay Gross. Together, they set out to redesign how healthcare reaches vulnerable populations, bringing clinicians, behavioural health specialists and social care workers directly into neighbourhoods, homes, shelters and community spaces.
The company’s early belief garnered backing. In 2018, Cityblock secured its first major investmentn of $20 million through seed financing led by Sidewalk Labs, signalling confidence in its mission. More funding followed as outcomes improved and its model drew national attention. To date, Cityblock has raised over $500 million from investors including General Catalyst, Tiger Global, and Alphabet affiliates, at one point reaching a valuation above $5 billion, positioning it among the most successful health innovation companies in America.
Under Dr. Ajayi’s leadership, she became CEO in 2022, the company has expanded into several U.S. states, deployed care teams that meaningfully reduce unnecessary hospital visits, and established professional pathways for community health workers. Today, Cityblock employs more than 1,000 people, including clinicians, technologists, data scientists, community health partners and operational staff.
Recognition soon followed her achievements. Dr. Ajayi was named to Fortune’s 40 Under 40 and profiled by Forbes, Bloomberg and the Financial Times as one of the most influential voices in health equity. Her public speaking blends policy insight with humanity, informed by years spent sitting with patients whose vulnerabilities shaped her calling. In 2024, she was elected a member of the National Academy of Medicine.
Despite success, her journey has not been without obstacles. Cityblock operates in the most complex corner of healthcare, navigating regulatory hurdles, insurer relationships and communities historically mistrustful of institutions. The COVID-19 pandemic further tested the organisation as needs surged dramatically among the people it serves. Yet Dr. Ajayi’s resilience reflects familiar traits within the Nigerian diaspora, quiet determination and a conviction that systems can be reimagined in service of the marginalized.
As Cityblock looks forward, Dr. Ajayi sees opportunity to expand models of care across more regions, influence Medicaid policy reform, scale programs tackling maternal and behavioural health, and continue proving that healthcare must evolve beyond clinic walls.
Her story remains in motion, but one truth is clear: she is not merely running a company, she is helping rewrite what healthcare can and should mean for people who are often forgotten. In doing so, Dr. Toyin Ajayi stands among a generation of Nigerians reshaping global sectors through education, innovation and service.
Her future promises still wider impact as she pushes healthcare toward equity, dignity and measurable transformation, an aspiration deeply tied to where she comes from and what she believes systems must become.
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