He received a Bachelor of Science degree from Northwestern University in 1977, and a Juris Doctor from Harvard Law School in 1981.

He later was a special counsel and chief of staff to Robert Mueller, the assistant attorney general of the Criminal Division at the United States Department of Justice from 1990 to 1993.

While at Goodwin Procter, Saylor represented Circor International, Inc., KF Industries, Inc., and senior company officials as a criminal defense attorney while those companies were under investigation for smuggling Chinese-manufactured valves and selling the valves as a product of the U.S. between 2001 and 2004.

[1] The U.S. Attorney for the Southern District of Texas, Michael T. Shelby, dismissed the investigation days after Saylor was confirmed by the Senate.

He also served a term on the United States Foreign Intelligence Surveillance Court from 2011 to 2018.