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Alyssa  Mastromonaco

Alyssa Mastromonaco

Former White House Deputy, New York Times Best-Selling Author & Crooked Media Contributor


As the youngest woman ever to be Deputy Chief of Operations at the White House, Alyssa Mastromonaco kept our country running through a government shutdown, natural disasters, national tragedies and history-making events. A key figure in the "Sisterhood of the Administration 44," she made the presence of women felt and their voices heard – redefining the traditional White House boy's club culture. Mastromonaco chronicled her time in Obama’s inner circle in her acclaimed New York Times bestseller Who Thought This Was a Good Idea? And Other Questions You Should Have Answers to When You Work in the White House. She followed with her current book, So Here's the Thing...: Notes on Growing Up, Getting Older, and Trusting Your Gut, described as a "twenty-first century girl’s guide to life." Featuring reflections, essays and interviews on topics important to young women, ranging from politics and career to motherhood and making and sustaining relationships in the age of social media, So Here's the Thing showcases Mastromonaco's signature humor and disarming candor. Now speaking, writing and commenting on subjects ranging from our current political landscape to how to lead teams and handle crises, Mastromonaco combines an unfiltered style and irreverent humor with wisdom and stories gained in the White House, corporate America and as an outspoken voice in media. Read More >

Following the White House, Mastromonaco served as COO of Vice Media and President of Global Communications and Strategy at A&E Networks. She is currently a co-host of HYSTERIA!, Crooked Media’s all-woman produced podcast. She also contributes to Crooked Media’s Pod Save America, is a contributing editor to Marie-Claire and serves as Senior Advisor and spokesperson for NARAL Pro-Choice America. Before her position as a White House Deputy, she spent a decade working for Barack Obama in various roles, beginning as Director of Scheduling for his 2004 U.S. Senate Campaign. In 2011, she was named President Obama’s Deputy Chief of Staff of Operations, responsible for running and managing the entire 18-acre White House compound and the 1,700+ employees in the executive branch. She was the youngest woman ever to hold this position and was included on the New Republic's list of "Washington's Most Powerful, Least Famous People." Mastromonaco's career in politics began as an intern for Vermont Senator Bernie Sanders and Director of Scheduling for John Kerry’s presidential campaign. A veteran of three presidential campaigns, Mastromonaco is consistently named as a Democratic power player in the upcoming 2020 presidential elections.

Sharing what one reviewer called "juicy stories from one of the world’s most glamorous jobs" with unvarnished advice on life, leadership and overcoming challenges, Mastromonaco takes audiences on an inspiring journey from her beginnings in small town America to the Oval Office to the corporate world and beyond. Read Less ^

Speaker Videos

College of Saint Benedict Commencement Address

Who Thought This Was A Good Idea? A Book Conversation

2014 Fergus Leadership Lecture

Speech Topics

So Here’s the Thing: Alyssa’s Guide to Work & Life

Called "a bold, no-nonsense, and no-holds-barred twenty-first-century girl’s guide to life," Alyssa Mastromonaco's newest best-seller tackles the topics important to young women (relevant to all stages of life), ranging from politics and career to motherhood, sisterhood and making and sustaining relationships in the age of social media. In this candid conversation, the Crooked Media contributor and former Obama Deputy Chief of Staff brings life lessons, behind the scenes looks at the White House and other juicy stories from her book to the speaking stage. Wise, honest and uproariously funny (with very candid Q&A) Alyssa showcases why, as Stacy London wrote, "everyone who knows her or reads her work wants to be Alyssa’s best friend."

Lean Out: How to Be Your Own Chief of Staff

Want top-tier advice on being your best, most productive, check-it-off-the-mile-long-to-do-list self? Ask New York Times best-selling author and Crooked Media contributor Alyssa Mastromonaco. As White House Deputy Chief of Staff, she was the first woman to occupy the office next to the Oval Office. Tackling job responsibilities such as vetting of cabinet secretaries and overseeing the Military Office (think Air Force One and Camp David), really teaches you how to get s*%t done. According to Alyssa, becoming the chief of staff of your own life doesn’t necessarily boil down to waking up at 5 a.m., drinking green juice, looking perfect and making millions while saving the whales. (Although if that’s your jam, go for it.) It’s about knowing what you have to do, how you are going to get it done and then, actually doing it. In this highly entertaining talk that celebrates the value of to-do lists and the power of self-forgiveness, Alyssa shares game-changing strategies learned in the White House and on the campaign trail that will help you “lean out” and finally become the boss of yourself.

Persistence is Part of the Game

A true trailblazer for women, Alyssa Mastromonaco is the former Deputy Chief of Staff for Operations at the White House and the youngest female to hold a White House Chief of Staff position. Upon leaving her long time role, Alyssa’s next endeavor is to “pay it forward” — to share creative strategies and lessons learned to encourage and empower all women to be trailblazers in their own careers and lives. With such themes as the power of persistence, strategic planning, risk-taking in decision-making and mentoring, Alyssa’s extraordinary, engaging and fascinating stories illustrate true takeaways that will be impactful to all audiences. In addition, her unique insights will inspire women from all walks of life to take their game to the next level.

Girl Power: Empowering Women to Lead by Example

As the former Deputy Chief of Staff for Operations at the White House, Alyssa Mastromonaco knows a lot about the power women possess. In this speech, Mastromonaco shares stories from her life to show women how to break the glass ceiling and establish fulfilling careers. Being one of the few people to have the rare opportunity to work alongside President Obama, she provides a unique perspective on how women can be successful in the workforce today and achieve positions that are traditionally dominated by men. Sharing her own successes and failures, Mastromonaco encourages women to lead by intelligent empowerment and become examples to future generations of girls.