After many years of rising through the ranks of the United States Postal Service, Henderson was appointed as the United States Postmaster General by the Governors of the U.S. Postal Service, effective May 16, 1998.[2] He was the fifth career employee to lead the world's largest postal system.[1] On May 31, 2001, Henderson's contract as the United States Postmaster General expired and he stepped down.[3]
In January 2006, Henderson became the chief operations officer at Netflix.[4][1]
Henderson is a director of LiveRamp. His total 2010 remuneration for this role was $100,000.[5]
In 2011, Henderson founded Hold The Eye Images, Inc.[6]