[1] Sherman worked in private practice as an attorney at a small Boston firm during the 1980s, as well as at Eckert Seamans Cherin & Mellot, LLC.

[1] From 2002 to 2004, Sherman was co-lead counsel representing claimants in a sexual abuse lawsuit against the Roman Catholic Archdiocese of Boston.

[2] Sherman's first official act as ambassador was speaking at the Carlucci American International School of Lisbon for the graduation of its senior class on 1 June 2014.

[10] Shortly after his ambassadorship, he was awarded the Order of Prince Henry by President Marcelo Rebelo de Sousa, during a ceremony at the Hall of Ambassadors, in Belém Palace.

"[11] On October 13, 2017, Lone Star Funds, owner of 75% of the bank Novo Banco, announced Sherman would become a member of the General and Supervising Committee (Portuguese: Conselho Geral e de Supervisão) of the latter.