Jackson, an upstate New York native, started his professional career broadcasting for the Utica Devils after graduating from Syracuse University. In 1993, he became the radio play-by-play broadcaster for the Philadelphia Flyers, replacing Gene Hart who had gone back onto television. Two seasons later, Jackson was promoted to the television side where he remains to this day. 2007-08 marked his fifteenth season as the main voice of the club.
Due to the fact that Jackson basically filled the shoes of legendary Flyers broadcaster Hart, Mike Emrick only stayed for 5 years before taking the same job for the New Jersey Devils), Flyers fans initially had mixed opinions on Jackson, with some taking a neutral stance. Jackson's broadcasting style is neither flamboyant nor monotonous, but most would agree that his holding on to the position speaks volumes of Jackson's abilities.