Kevin Cummings ’97

Championing Community and Education

Through his career in nonprofit educational settings, Kevin Cummings ’97 is expanding his own community, and that of others.

BY JANA F. BROWN

Growing up in Crown Heights, Brooklyn, as the son of Jamaican immigrants, Kevin Cummings ’97 defined his community as the block he lived on — the neighbors, the friends and the businesses, including his mother’s hair salon.

Boarding school was not something Cummings imagined for himself until he had the opportunity to attend St. Paul’s School through Oliver Scholars, a program that prepares high-achieving Black and Latinx students from underserved NYC communities for top independent schools. Cummings credits his parents, extended family and friends with “putting money together to buy me a jacket, buy me boots, buy me a bag. It was a lot of people giving bits and pieces to do that, so I felt like my experience was representing many people.”

It was at SPS, where several faculty members supported him, that Cummings gained the broader perspective that has influenced his post-high school years in the nonprofit educational sector, most recently with City Year, which partners with high-need communities. The organization, which recruits young adults ages 18 to 24 to devote a year of service as student success mentors in schools, was founded by Alan Khazei ’79 — though Cummings didn’t know that when he signed on.

“Being at St. Paul’s made me recognize that my community could be bigger than my block,” says Cummings, who serves as City Year’s senior vice president of district engagement. “The multiple levels of exposure to people from different places played a critical role in how I decided to define community.”

Cummings built community during his time at SPS both on campus and through volunteering with the Boys & Girls Club of Concord, where he realized he enjoyed lifting up others. “[Service] was how I started to define how I was going to make my St. Paul’s experience matter,” says Cummings, who always intended to return to Brooklyn. “The thread that connects all these things is that I endeavor to improve the quality of life of communities I can impact.”

Since graduating from Williams College with a degree in psychology, Cummings has held a series of service-focused roles, including with the After School Academy at the Boys’ Club of New York; 10 years in NYC government supporting efforts in education, equity, public-private partnerships and economic opportunity; and serving as director of the NYC Civic Corps AmeriCorps program.

His first stint at City Year (2007-10) was as a recruitment director responsible for engaging young adults to serve in New York’s schools. In 2022, Cummings rejoined City Year from his home base on the south side of Brooklyn. His current role involves overseeing sites around the country in their partnerships with school districts.

“[Service] was how I started to define how I was going to make my St. Paul’s experience matter.”

Although City Year’s efforts are at times challenged by school districts grappling with funding priorities, local shifts in education policies, and a need to center youth agency, academic development and personal development, Cummings believes the organization, driven by an engaged generation, is positioned to advance change.

“Districts have become much more challenged by how they will continue to provide what they consider priority services to their young people,” Cummings explains. “We’re a bipartisan organization, so we try to make people understand that we’re helping to advance the opportunity to center youth in their educational experience. We’re conscious of the importance of meeting the needs of young people; they are the ones that do, and will, drive City Year.”

As part of his district engagement responsibilities, Cummings supports City Year executive directors in partnerships with schools in Ohio, Michigan, Oklahoma, Florida, Wisconsin, Texas, Missouri, Colorado and Tennessee. He guides them in problem-solving and helps them promote social impact and educational equity in each district. Cummings describes himself as an ameliorator and considers his time in New Hampshire as a catalyst for his desire to leave things better than he finds them.

“I realized I was having a different type of experience that I wanted to make matter,” he says. “Going into a nonprofit space in education, I knew I wanted to be a teacher but not a traditional teacher. I knew there was value in growing my community more than my own block. Now, I’m trying to leverage everyone to do that.”