Government Contractors | Technology 2025: CALKINS, MATT

A top economics graduate at Dartmouth and a world champion board gamer, Calkins co-founded cloud computing and enterprise software firm Appian in his basement in 1999. It grew to become the most successful software IPO of 2017.

In 2024, Appian reaped $68 million in cloud subscription revenue, up 21% compared with 2023. The company’s total 2024 revenue was $617 million, an annual increase of 13%, achieved after the company laid off 150 of its 2,243 workers to boost profits.

Calkins worked at software company MicroStrategy before forming Appian. He has served on the board of the University of Virginia’s Sorensen Institute for Political Leadership, the Northern Virginia Technology Council and sits on the Virginia Public Access Project’s leadership council.
Calkins has said he sees opportunity for Appian to pick up new business due to its close work with the Department of Government Efficiency on federal streamlining and the Trump administration’s scrutiny of larger contractors.

In March, the Virginia Supreme Court agreed to hear a petition from Appian seeking to reinstate a record $2.04 billion verdict in a 2022 corporate espionage case against rival Pegasystems that was previously overturned.