Hartford Mayor Arulampalam announces new leadership

A Hartford Healthcare executive and Trinity College graduate has been named Hartford’s new Chief Operating Officer.

Mayor Arunan Arulampalam announced Olusegun ‘Shay’ Ajayi will step into the position next month.

Ajayi currently serves as the Vice President and Chief of Staff at Hartford HealthCare, according to a release from the mayor’s office. In his role, Ajayi oversees and directs the work of Hartford HealthCare President and CEO Jeff Flaks. In addition, Ajayi collaborates with executive teams and the community on the implementation and creation of strategic initiatives and programs. Prior to his role as Vice President, he served as Director of Operations at Hartford Hospital, and in various roles at The Hartford Financial Services Group before that.

“During Shay’s time with Hartford HealthCare, Shay has operationalized large and small projects, leaving a profound impact on the organization,” Flaks said in a press release. “He is highly regarded as a person of integrity and compassion, and he is a consummate team player, making him the ideal candidate for the Chief Operating role.

The mayor said he will formally submit his name to the city council for confirmation during the Feb. 26, meeting, and Ajayi will start work on March 18.

“I am confident that he is prepared to hit the ground running on day one to fulfill the important responsibilities of the COO and help make City Hall more effective and responsive to the needs of our community.  As a Trinity College alum and an active resident of our community, he cares deeply about this city, and we are grateful that he will be joining our talented, diverse team,” Arulampalam said.

Ajayi will replace outgoing Thea Montanez, who will continue to serve on an interim basis until March 15, according to the city. Montanez had served as the Chief Operating Officer under former mayor Luke Bronin. Montanez, who has held the role since 2020, is credited for helping to lead the city through the COVID-19 pandemic.

“It is truly an honor and a privilege to have this opportunity to serve Hartford, and I look forward to collaborating with the thousands of public servants across all of our city departments and supporting their commitment to serve our residents,” Ajayi said. “I made Hartford my home because it is a beautiful place with great people, people I’ve had the chance to learn from and work alongside. I believe in Hartford, I believe in this team, and I look forward to working with Mayor Arulampalam and his administration, advancing new initiatives and building on past efforts to continue making the City of Hartford a great city to live, work and play.”

Ajayi earned his bachelor’s degree in economics and engineering science from Trinity College and is currently a Master of Business Administration student at Columbia University.

“Thea has poured her heart and soul into serving the City of Hartford over the last eight years,” Arulampalam said. “She helped lead this city through some of its most unprecedented and challenging times, and she created and spearheaded initiatives that will make a lasting impact on our community. I’m deeply grateful that she has stayed with the city through this transition period.”

Stephen Underwood can be reached at sunderwood@courant.com

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