Olusegun “Shay” Ajayi ’16

Olusegun “Shay” Ajayi has been appointed to serve as the chief operating officer for the City of Hartford effective March 18, 2024. Prior to this most recent appointment, he served as vice president and chief of staff at Hartford Hospital, a division of Hartford HealthCare, where he oversaw the work of the Office of the President, collaborating with executive teams and the community on the implementation and creation of strategic initiatives and programs. As a member of the administrative cabinet, he led operations, strategic development, and planning for the organization and provides leadership of key ancillary and support service departments. Ajayi previously worked as a program lead for Sports Changes Life, a nonprofit organization based in Northern Ireland, while playing professional basketball on Ireland’s National League team. Prior to that, he worked as a business intelligence consultant at The Hartford Financial Services Group. Ajayi continues to offer his time as a volunteer assistant coach and mentor for Trinity’s men’s basketball team.

Ajayi earned a B.S. in economics and engineering science from Trinity, where he also served as captain of the men’s basketball team and was honored as an NABC Division III All-American and NESCAC Player of the Year. He went on to earn an M.S. in sports psychology from Ulster University in the United Kingdom. He currently is an executive M.B.A. candidate at Columbia University.

Ajayi resides in Hartford.