Born in Willow Springs, Missouri, Bolerjack graduated from Shawnee Mission Northwest High School in Shawnee Mission, Kansas. He enrolled at Kansas State University and walked on to the Kansas State Wildcats football team as a linebacker, but left the team after fall camp due to an ACL injury. While attending college, he worked as sports director for the campus radio station KSDB. Bolerjack is also an alumni member of Delta Upsilon Kansas State chapter. He began his television broadcast career as a weekend sports anchor for KTSB-TV Topeka (now KSNT).
He and Steve Beuerlein were the secondary college football broadcast team for CBS Sports. They were on the air when two games were scheduled on the network on the same day. He also was a reserve broadcaster for the NFL on CBS. In 2007, Bolerjack filled in for Greg Gumbel, who was filling in for an ill James Brown, on the Cleveland Browns-Arizona Cardinals matchup with Dan Dierdorf. He also worked with Rich Baldinger, Todd Blackledge, Mike Mayock, and FOX colleague Daryl Johnston.
Before joining CBS, he was the sports anchor at KSL-TV, Salt Lake City, Utah.
In addition to his other work, Bolerjack is the voice of the Utah Jazz. He replaced "Hot Rod" Hundley on the television broadcasts during the 2005–06 NBA season. (Hundley continued to announce on the radio, but announced his retirement after the 2008–09 NBA season.) His on-air partner, Matt Harpring, is former Utah Jazzman. Harpring began doing the TV broadcasts starting with the season (2010–2011), when Ron Boone moved over to the radio broadcasts. He was also the preseason voice of the Miami Dolphins until he was replaced by Dick Stockton.
Bolerjack lives in Sandy, Utah with his wife, Sharon, and his three children. Bolerjack called Pac-12 games on Fox Sports Net with Joel Klatt and Petros Papadakis in 2011 and continues to perform the same role for FX and Fox College Football, along with CBS and Fox colleague Gus Johnson. In 2011, Bolerjack filled in for Stockton in the NFL on Fox TV broadcast booth for the week 4 matchup between the Atlanta Falcons and Seattle Seahawks with John Lynch.