Alyssa Mastro

Alyssa Mende Mastromonaco is an American author, podcaster, spokeswoman, and former government official. She served as White House Deputy Chief of Staff for operations in the administration of President Barack Obama from 2011 to 2014. She was the youngest woman to hold that position. She was later President of Global Communications Strategy & Talent at A&E Networks and the chief operating officer of Vice Media.

She has also been a contributing editor at Marie Claire magazine. Since 2017, Mastromonaco has been a podcaster with Crooked Media. Mastromonaco grew up in Rhinebeck, New York. Her father was a business consultant, and her mother was a high school lunch aide. In 1994, she graduated from Rhinebeck High School. During high school, Mastromonaco worked various jobs, including her first job as a checkout at a grocery store called Kilmer's IGA.

Mastromonaco went to the University of Vermont for two years, majoring in French with a minor in Japanese. She then transferred to the University of Wisconsin-Madison, where she graduated with a Bachelor of Arts in political science in 1998.

The summer after her sophomore year of college, after seeing then-Congressman Bernie Sanders speak on campus, Mastromonaco was hired by Philip Fiermonte to work as an intern for Sanders in his Burlington, Vermont, district office. At that time, Sanders was campaigning for his fourth term in the United States House of Representatives. Mastromonaco has said that the experience inspired her to work in government after seeing how it was possible to help people doing constituent work on a grassroots level. 

Although she had transferred to Wisconsin to study French, the summer working for Sanders shifted her passion from studying French and Japanese to studying political science. She cites Fiermonte as a great mentor during an important time in her life. The next summer, Mastromonaco was invited to work for Sanders in Washington, D.C.

After college, Mastromonaco wanted to continue working in government but couldn't find a job, so she worked as a real-estate investment-trust paralegal, which she said was instrumental in teaching her how to work well as part of a team. The job was in the World Trade Center.

In 2000, Mastromonaco moved to Boston and got her first job in politics as a staff assistant to Senator John Kerry. For a short time, after 9/11, she worked at a Republican lobbyist group, Richard Berman's American Beverage Institute, as director of membership. In 2002, Mastromonaco was hired as Press Secretary for Congressman Rick Boucher of Virginia, but in December 2002 went back to work for Kerry. In 2004, Mastromonaco was hired as the director of scheduling for Kerry's presidential campaign.