In the 1990s, Cutter worked as a junior aide to Mario Cuomo and also worked for the Environmental Protection Agency. She worked for President Bill Clinton as Deputy Communications Director at the White House during his administration "to help restore Mr. Clinton’s image in the aftermath of impeachment and Monica Lewinsky", and as Associate Administrator for Communications at the U.S. Environmental Protection Agency. Beginning in 2001, she served as Communications Director for Senator Ted Kennedy. In November 2003, she was named communications director for the John Kerry campaign, at Kennedy's recommendation. During that campaign, she was criticized for having a surly and difficult personality and was often scapegoated for Kerry's loss. Kerry considered the criticism of her unfair and praised her work. After the Kerry campaign, Cutter returned to work for Kennedy. In June 2008 Cutter was appointed Chief of Staff to Michelle Obama for the 2008 Presidential general election campaign. Stephanie Cutter and Michelle Obama immediately clicked and Cutter is widely credited with building Obama's popularity with the public, particularly her Let's Move! health initiative. She is credited with enlisting Republican Mike Huckabee to the program, to help prevent criticism from conservatives. She served as the Chief Spokesperson for the Obama-Biden Transition Project. She served in the Treasury Department as Timothy Geithner's counselor where "she protected Geithner’s fragile reputation and tried to spin unpopular policies like the Troubled Asset Relief Program and the A.I.G. bailout." In May 2009, Cutter was appointed to serve as adviser to President Obama in the Supreme Court nominations. Later that year, GQ Magazine named Cutter one of the 50 most powerful people in Washington. In 2010, Cutter was named Assistant to the President for Special Projects, charged with managing communications and outreach strategy for the Patient Protection and Affordable Care Act. In 2011, Cutter was named Deputy Senior Advisor to President Barack Obama. In September 2011, the White House announced Cutter would leave her position as Deputy Senior Advisor to serve as deputy campaign manager for Obama for America. She has appeared in numerous campaign videos and ads for Obama's campaign, as well as a guest in TV appearances. During the 2012 campaign, Steve Schmidt, a Republican strategist, stated that Cutter is "arguably the strongest player on either side out there now." CNN announced on June 26, 2013, that Cutter will join a new version of Crossfire re-launching in the fall of 2013, with panelists Newt Gingrich, S. E. Cupp, and Van Jones. Besides her role at CNN Cutter founded Precision Strategies, where she is a partner. Precision Strategies is a strategic consulting firm based in Washington D.C. and New York City. Cutter started the firm with three veterans that worked for the Obama 2012 campaign team. Cutter informed CNN staffers on October 7, 2013 that she was pregnant with her first child. With a due date of early March 2014, she informed the network she would return to Crossfire after maternity leave. She remained with the series until it ended in July of that year.
