Shawn O’Leary is our Executive Vice President who joined the Dirigo Safety LLC in 2016. Also, he oversees our Policy Development Services, Online Training Programs for Maine Law Enforcement agencies, Executive Selection, and Recruitment Services, Supervisory Promotional Examinations & Assessment Center Services.
He also oversees our Workplace Violence training and On-Site Security Assessments products. He provides a sense of ease and understanding for those clients he interacts with while ensuring that they gain critical information through superior customer service. Shawn has over 36 years of law enforcement experience, 15 of which have been at the Command Level and Senior Executive Level.
He started his career as a summer reserve in coastal communities while attending college. He was later selected by the Brunswick Police Department in 1988 where he stayed until his retirement as a Lieutenant in 2008. He then moved onto working at the Cumberland County Sheriff’s Office. At the rank of Captain, he oversaw the Support Services Division and then the Criminal Investigations Division until 2014. In 2020 he retired as the Chief of Police for the Town of Winslow, Maine. Shawn’s extensive work experience is only part of his background and his education has played a crucial role in Dirigo Safety.
He is a 2013 Graduate of the prestigious FBI –National Academy. Has a Bachelor’s Degree, with Honors, in Business Administration/Human Resource Management from Southern New Hampshire University and an Associate’s Degree in Criminal Justice from Bangor Community College. Shawn has been recognized for his accomplishments many times over his career which include –2015 Police Chief of the Year –“David W. Pickering Award”,2019 Awarded “Law Enforcement Executive Certificate” from the Maine Criminal Justice Academy Trustee’s, 2009 “Heroism Award”, 2001 “Meritorious Service Award”, and recognized many times for his superior performance, where he received Commendations for Bravery, Leadership and Investigative Excellence.