In a straight line of connect-the-dots, you could show that the Martin Luther King, Jr. Scholarship took 2008 Stonington High School graduate Rayshawn Whitford halfway around the world and back.
Whitford, now 31 and living in Detroit with a new position as program manager for employees at Twitter, was a football and lacrosse star at Stonington High School. His mother, Raylene Whitford struggled financially, raising three sons as a single mother working swing shift at Foxwoods Resort Casino and driving a school bus.
Young Rayshawn, the oldest boy, suffered with severe asthma at times, but his mother said he never wanted to miss school. One teacher called him “a sponge,” she recalled, and she never had to push him to do schoolwork.
As Rayshawn entered high school, financial struggles forced the family to move a lot. They lived in Norwich, Pawcatuck, Westerly and Groton.
To stabilize his high school years, Rayshawn moved in with his older cousin, Stacy Lowry, his mother’s niece, who was raising two young boys at her Pawcatuck home. Lowry became like a second mother and mentor. Rayshawn became a male role model for her young boys, as Lowry too was raising her family as a single mom.
Lowry’s boys, Kyle and Luke, were 2 and 1 when Rayshawn moved in. Kyle was born with hemifacial microsomia, a congenital condition in which some facial tissues do not develop properly.
“He has this really special bond with my kids, just growing up himself without a stable father figure,” Lowry said of Whitford.
Teenage Rayshawn taught the kids to make giant pancakes they are called “mancakes.” He took them to ice cream stands where they had ice cream eating contests.
Lowry had been the first in their family to graduate college, and Rayshawn wanted to become the second. He earned a bachelor of science degree in accounting at the University of Connecticut and a master’s degree in business administration at Rensselaer Polytechnic Institute. She is chief financial officer at the Waterford Country School.
Good grades, sports, student government, peer projects and clubs helped him apply for all kinds of scholarships, because even with full academic funding offered by colleges, he still lacked money for room and board and other costs. He did not know how he would do it.
He was awarded the Martin Luther King, Jr. Trust Fund Scholarship, $5,000 per year for four years, in fall of 2007, his senior year at Stonington High School.
“The Martin Luther King Scholarship was huge,” Whitford said. “It was an affirmation that all the hard work I put in was worth it. It really opened a lot of doors.”
During a campus visit to Babson College in Wellesley, Mass., Whitford fell in love with the entrepreneurial approach and intense focus by students. He was accepted on full scholarship.
Whitford at first majored in accounting, a career he felt would bring him financial success and stability. After one year at Babson, he was burnt out and just wanted to go home and sleep for the summer.
Instead, academic advisor, Kim Gibbs steered him to Babson’s entrepreneurial program in South Africa, where he would teach high school students in Kayamandi Township in partnership with students at Stellenbosch University.
His eyes opened when he realized how students there struggled and were so determined to succeed. One student, Frank, was older than Whitford. Frank sold newspapers and did any jobs he could find to pay for school, Whitford said.
“I got a letter from him six or seven years later saying he graduated and was doing very well,” Whitford said. “It was exciting to see he was doing really well.”
The following summer, Whitford landed an internship at the gold standard firm for accounting majors, Price Waterhouse Coopers, one of the largest professional services and accounting firms. But the technical, tedious tasks he was assigned left him unfulfilled.
“I went back and dropped all my accounting classes,” he recalled. He worked with academic advisor Gibbs to rework his major into entrepreneurial ventures. One class on affordable design and entrepreneurship focused on finding practical solutions to social issues in places all over the world, from Mississippi to India to Ghana.
He figured he either would work for nonprofits or work somewhere abroad. The latter was his first opportunity. Whitford spent the summer of 2011 in Ghana, and upon graduating Babson in 2012 with a bachelor of science degree in business with a concentration on international development, Whitford was hired to run Babson’s entrepreneurial programs in East Africa.
After three years, he returned to the United States and spent seven years working for The Bridgespan Group, a consulting firm that helps nonprofits and non-government organizations with leadership and collaboration efforts. Whitford said he was proud that he successfully transitioned Babson’s program in East Africa into an all local, African staff, including a Rwandan Babson graduate to take his place.
Based in Boston for Bridgespan, Whitford became a frequent flyer, traveling across the country to meet with nonprofit clients. He flew most often to Detroit, where he said one Detroit airport TSA agent came to know him by name. He fell in love with the Motor City, he said, and people there who rally together to overcome stereotypes that the city is a “murder capital” or a failed city.
COVID-19 grounded Whitford. He shifted to remote work and moved back to Stonington for a time. But he missed big city life and missed Detroit. So he pursued and landed the position at Twitter last fall. Now, he works at his home office in Detroit, while still rooting for his Boston sports teams.
“COVID really opened up a whole new world for me,” Whitford said. “I hadn’t realized how strange a lifestyle I was living until I couldn’t do it anymore.”
At Twitter, Whitford oversees programs on “building healthy teams,” ensuring employees have a psychologically safe environment and are comfortable to build working relationships, which also helps them deal with outside pressures that affect work, Whitford said.
Raylene Whitford credits all three of her sons for their determination to overcome their childhood family financial struggles and instability. Rayshawn’s brothers, Josh Whitford, now 30, is a US Air Force tech sergeant stationed in Pensacola, Fla. Jason Whitford, 26, is an EMT in New London, planning to get a degree in nursing.
“I thank God every day,” Raylene Whitford said. “I, myself, do not have a great education. I’m a SEAT bus driver all over southeastern Connecticut. They get all the credit. They’re the ones who had the tenacity to push through.”
Rayshawn Whitford never forgot the boost he received with the Martin Luther King scholarship. Every year at Babson, he participated in Martin Luther King Day events. One year, he won a speech contest with a cash award. He donated half of it to the New London County Martin Luther King, Jr. Scholarship Trust.
This year, Whitford will sponsor a full $20,000 King scholar for the first time, covering the four-year cash award he had received back in 2007.
“I’m super grateful to have gotten the scholarship,” Whitford said. “I really do believe deeply in the scholarship trust. I have since I was 18.”