After graduation, Massoudi worked for Mayor of Toronto, Rob Ford, including as his communications director [4][5] In 2013, he denied allegations reported by Vice News[6] that he had hired a hacker to destroy a video that showed Rob Ford smoking crack cocaine.[7]
After his time working for Rob Ford, Massoudi worked as strategic adviser with Amir Remtulla & Associates and also as a senior consultant with Capitol Hill Group.[4][8] Massoudi then worked as an executive assistant for Toronto City Councillor Doug Ford.[4][5] In 2019, when Doug Ford was the Ontario Premier, Massoudi was promoted from his deputy chief of staff to his principal secretary.[5][9] During the 2022 Ontario general election, Massoudi was the chair of the Progressive Conservative Party of Ontario's re-election campaign.[1][10]
In July 2022, the Toronto Star reported that Massoudi is leaving his government job to work in the private sector.[1]