He was born in Indiana, Pennsylvania to musical parents. His mother Paula and father Nevin are music teachers for Purchase Line and Indiana Area School Districts respectively, and his brother is a music educator in Indiana Area School District. He began playing drums at age 3 and was in a jazz trio called Paj 3 with bassist Phil Kuehn (a fellow Indiana native) and pianist Angelo Versace throughout high school.
Saylor graduated from Indiana Area Senior High School in 2004, and later attended the Manhattan School of Music and the Juilliard School.
Saylor plays percussion in Jonathan Batiste’s Stay Human, the house band for The Late Show with Stephen Colbert. He also performs at various jazz clubs, festivals, and venues around the world. He has conducted jazz workshops at various educational institutions including the prestigious Stanford University. He has performed at such places as the Howard Theater the White House, Lincoln Center, Rockwood Music Hall, Webster hall, and the Great GoogaMooga. He has performed or recorded with Roy Hargrove, Wynton Marsalis, Dwayne Dolphin, Steve Wilson, Joe Lovano, Jon Faddis, Slide Hampton, and Ellis Marsalis.
He appeared on the cover and feature article of the April 2016 issue of Modern Drummer, was featured in the March 2014 issue of Drum Magazine, and appeared on the HBO series Treme in 2010.