Career Evolution for Class of 1991 Alumnus

8/22/2025

Class of 1991 alumnus Matthew Small has made the transition from law to management over his international career in the educational technology industry.

“The transition wasn’t too hard since I was working in mergers and acquisitions and running the integrations of the companies we acquired,” said Matthew. “I was always focused on the organizations.”

Matthew started that focus (and drive) with a bachelor's degree from the University of Denver. He then moved back to Connecticut to earn a four-year, dual degree from the University of Connecticut with a Master of Business Administration degree and Juris Doctor degree.

After grad school, Matthew started working at the law firm of Testa, Hurwitz & Thibeault, LLP in Boston. He planned, structured, and negotiated a broad range of technology company transactions for venture capital funds and startups that prospered during the technology boom of the late 90s and early 2000s.

“At that time, my fiancée (Davina) and I both had opportunities in Washington, D.C.,” recalled Matthew. “So, we moved from Boston to D.C. together, and I took a job as in-house counsel at Blackboard, where I worked for 14 years.”

Blackboard is an educational technology company where Matthew quickly worked his way up to become the youngest general council on the NASDAQ at that time.

From there, he transitioned from law to operations and became the chief business officer at Blackboard.

“I oversaw more than two dozen acquisitions and took Blackboard private in 2012,” recalled Matthew.

That worldwide experience set Matthew up to become Blackboard’s first international president.

“Blackboard was growing by leaps and bounds,” said Matthew. “It was an exciting time. We moved our family from D.C. to London. When we arrived, I needed to find an office, home, and a school for our children. Those were amazing years!”

Opportunity came knocking for Matthew in 2016, after he and his family moved back to D.C. to take the president and chief executive officer job at Symplicity Corporation, which is the international leader in higher education student services software.

Matthew and Davina have two children: Grey Bear Small is a rising junior at Brown University and Gunnar Wolf Small starts at Brown this fall.

“Our family is close,” said Matthew. “Thankfully, we are all into the same things, like the outdoors, travel, working out, music, and movies. We also own a place in Vermont where we love to camp, ski, and showmobile.”

Talk about a small world.

“My son Gunnar bumped into Mr. Bennett this summer at Camp Laurelwood in Madison, Conn.,” recalled Matthew. “He was my biology teacher at Hamden Hall.”

Matthew’s family also has other Hornet connections. His uncle, Leigh Small, sent six children through Hamden Hall: Andrew Small, Class of 2005, Kevin Small, Class of 2007, Patrick Couden, Class of 2008, Beau Couden, Class of 2009, Samantha Small, Class of 2012, and Barrett Couden, Class of 2014.

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Class of 1991 alumnus Matthew Small.

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