After graduating from Emerald Ridge in 2005, Wolcott initially enrolled in Pierce College, but decided to attend umpiring school instead.

He made his Major League debut on May 27, 2013, working both games of a doubleheader between the Arizona Diamondbacks and Texas Rangers.

[2][3] Wolcott was hired to the full-time Major League umpire roster on July 4, 2014, to replace Gary Darling, who had retired.

[4][5] Wolcott's first postseason assignment was the 2016 National League Wild Card Game between the San Francisco Giants and New York Mets.

[6][7] On September 13, 2017, Wolcott initiated a minor controversy by hinting that Detroit Tigers pitcher Buck Farmer and catcher John Hicks might have conspired to hit him intentionally after a controversial call that got then manager Brad Ausmus ejected.