Skyler worked at the New York City Department of Parks & Recreation from 1995 to 1999, where he served as deputy chief of staff and as the public information director.
In 2000, Skyler left Giuliani's administration to work at Bloomberg LP's Corporate Communications group.
Skyler served in that position through the transition during which time he was appointed Press Secretary to the incoming mayor.
In 2010 Skyler joined Citigroup as an Executive Vice President for Global Public Affairs.
[2] On March 4, 2009, Skyler, who stands 6 feet, 4 inches, tackled a mugger in midtown Manhattan after a young woman said she had just been robbed[3] and he recovered her BlackBerry.