DiPietro began his career at M&T Bank in Buffalo but left after a few years to work as a consultant to small businesses.

After serving as mayor for six years, he set his sights on higher office, running in the Republican primary for the 59th New York State Senate District against incumbent Dale Volker in 2008[1] and challenger Patrick Gallivan in 2010.

[3] He voted against proposed medical marijuana legislation, the Compassionate Care Act (Bill A6357), and motions dated June 3, 2013 (94-41) and May 27, 2014 (94-63).

[5] However, DiPietro voted for adding opioid-use disorder (addiction) to the list of conditions treatable by medical marijuana (Bill A09016) on June 6, 2018 (108-28).

[6] In 2019 Assemblyman DiPietro became the Assembly sponsor of Bill# A05498 which proposes a constitutional amendment to divide the state into three autonomous regions.