[4] Wolfson began his career in politics working for Nita Lowey as her chief of staff and press secretary, and was executive director of the Democratic Congressional Campaign Committee from 1998 to 2000.
[5] He served as communications director for the U.S. Senate campaigns of Charles Schumer (1998), Hillary Clinton (2000, 2006), and Ned Lamont (2006).
Wolfson was co-chief strategist and communications director for the Hillary Clinton 2008 presidential campaign, after which he became managing director at The Glover Park Group, a communications consulting firm based in Washington, D.C.[6] He advised the campaign of Bill Thompson for New York City Comptroller in 2005.
[7] Wolfson served as a strategic adviser to News Corp. in its public relations campaign against Nielsen Holdings.
From August to November 2008, Wolfson wrote a blog on The New Republic's website, called "The Flack", that covered the final months of the 2008 presidential campaign.