Olusegun “Shay” Ajayi ’16

Olusegun “Shay” Ajayi currently serves as the chief operating officer for the City of Hartford. Before this appointment, he was vice president and chief of staff at Hartford HealthCare, where he directed the Office of the President and partnered with executive leaders and community stakeholders to design and implement strategic initiatives and programs. Earlier, as director of operations at Hartford Hospital, an affiliate of Hartford HealthCare, he was a member of the hospital’s administrative cabinet, leading operations, strategic development, and planning while overseeing several key ancillary and support service departments.

Ajayi’s professional experience also includes serving as a program lead for Sports Changes Life, a nonprofit organization in Northern Ireland, during which he played professional basketball in Ireland’s National League. Prior to his work abroad, he was a business intelligence consultant with The Hartford Financial Services Group.

Ajayi holds a B.S. in economics and engineering science from Trinity, where he was captain of the men’s basketball team and earned recognition as an NABC Division III All-American and NESCAC Player of the Year. He was also honored with the Robert R. Bartlett Award for excellence in athletics and service to the campus community, as well as the George Sheldon McCook Trophy for athletic achievement, academic standing, and integrity. He remains actively involved with Trinity, volunteering his time to mentor and support the men’s basketball team. He later earned an M.S. in sports psychology from Ulster University in the United Kingdom and an M.B.A. from Columbia University.