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Alyssa  Mastromonaco

Alyssa Mastromonaco

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

Biography

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. The memoir has been optioned by producer/star Mindy Kaling as a TV series to follow in the footsteps of White House classics The West Wing and Veep. 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 (Secret Service code name: “Popsicle”) with wisdom and stories gained doing one of the most important and exciting jobs in the world. 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 working on her next book, Gut Feelings: A Young Woman’s Guide to the World (Spring 2019 release) and 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. Press accounts have linked her to women candidates including Oprah.

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

Management Under Pressure: Tips from the Obama Administration

Imagine managing the schedule of the President of the United States, plus overseeing a White House staff of 1,700 employees, managing the hiring process for all Executive political appointments and screening nominees for Cabinet positions? These are just some of the tasks Alyssa Mastromonaco performed as the former Deputy Chief of Staff for Operations at the White House. Read More >

As a trusted aide of President Obama for nine years, Mastromonaco shares the management strategies she used to ensure all White House operations flowed smoothly and seamlessly. She tells inside stories of her experiences and provides insights into how to draw the best out of your workforce — even in the most trying times — enabling your organization to run as efficiently and effectively as possible. Read Less ^

The Whitehouse Gatekeeper: Tales of Brave Leadership

She had one of the most important roles in the White House: the power to decide who got to see The President of the United States. To be in such a high position, she had to demonstrate an unbreakable inner strength, which allowed her to manage some of the most powerful people in America. What does it take to become a brave leader like Alyssa Mastromonaco, the former Deputy Chief of Staff for Operations at the White House? In this speech, Mastromonaco explains how she mastered the tenacity and decision-making needed in such a critical White House role. In addition, she shows audiences how to measure and take calculated risks, mitigate the failure of those risks and be more accepting of failure – all essential traits that contributed to her resounding success.

Crisis Management: Turning Negative Events into Positive Outcomes

As the former Deputy Chief of Staff for Operations at the White House, Alyssa Mastromonaco not only managed President Obama’s schedule, but also helped coordinate the response to all major national disasters during her time in the White House. From the most trying natural catastrophes to manmade crises, Mastromonaco was one of the key contributors to ensuring positive outcomes from negative events, even when her last minute decisions were guided by pure instinct. In her engaging speech, audiences will learn how to successfully manage crises of all sizes through teamwork, astute decision making and how to motivate people to find innovative solutions for handling emergencies so that they can achieve a positive outcome regardless of the challenges they face.

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.

From Childhood Dreams to White House Realities: The Inspiring Teachers Behind My Journey

As the youngest female Deputy Chief of Staff for Operations at the White House, Alyssa Mastromonaco often reflects on all the inspiring teachers who empowered her and gave her the confidence to pursue her dreams. In this captivating speech, Mastromonaco shares personal stories of the people who led her down the successful path to where she is today. In addition, she speaks on why education is so important and how parents and teachers can properly mentor children so they can reach their highest potential and achieve their dreams.