Chief Pilecki is a 34-year veteran of the Wellesley Police Department, having been appointed to the department in July of 1983. The Chief served as a patrolman until 1992, when he was appointed as the department's court prosecutor. The Court Prosecutor acts as a liaison between the Wellesley Police Department and the Dedham District Court.
In 1997, Chief Pilecki was promoted to sergeant where he supervised the evening and overnight shifts in the Patrol Division. In 2001, Chief Pilecki was promoted to the rank of Lieutenant, and commanded the entire patrol division as well as the Emergency Communication Center.
In 2013, Chief Pilecki was promoted to the rank of Deputy Chief. As Deputy Chief, he oversaw the day to day operation of the department, as well as large scale events and incidents. Chief Pilecki implemented much of the changes that occurred to Boston Marathon security in Wellesley following the 2013 Boston bombings. This was a significant task, and Chief Pilecki worked and coordinated with many other local, state, and federal agencies during the transition.
Chief Pilecki also currently serves as the chair of the Wellesley Traffic Committee, a collaborative group comprised of town departments that solves long term traffic issues within the town.
Chief Pilecki is Wellesley's 9th Chief of Police since the department's inception in 1893.