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Matt Flanagan has a diverse work experience spanning over several years. Matt started their career in 1994 at ReTele Communications, Inc., where they worked as a Sales Executive, focusing on major enterprise account sales of Nortel, AVAYA, and Cisco telecommunication systems. Matt stayed with the company until 2011.

In 2009, Matt became an Executive Board Member at the John Patrick Flanagan Foundation, a position they still hold. Matt also joined the Harvard Athletic Association as a Board Member in the same year.

In 2011, they joined Rincon Technology, Inc. as a Strategic Account Executive. At Rincon Technology, they helped major cable operators, wireless providers, CLECs, and fiber network operators manage and grow their networks. Matt was responsible for buying, selling, and trading surplus and previously used network hardware, which allowed customers to re-capture value on displaced assets while lowering capital expenditures.

Additionally, Matt has been involved with Harvard Blues FC since 2011 as a Manager/Player.

Matt Flanagan attended Fairfield College Preparatory School, however, the start and end years of their attendance are unknown. Matt later went on to attend Boston College, but no information regarding the degree or field of study is provided.