Shawn O’Leary

Law Enforcement Services Manager

Shawn O’Leary is our Law Enforcement Services Manager who joined the Dirigo Safety LLC., 2016. 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, and On-Site Security Risk 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, 16 of which have been at the Command Level, and Senior Executive Level. During his career in law enforcement, he has worked in several units including Patrol and Undercover Operations for the Maine Drug Enforcement Agency. Shawn was a member of the Special Response Team for the Town of Brunswick for 10 years, the Primary Use of Force Instructor, which included being Maine Criminal Justice Academy Certified Instructor in Firearms and Interactive Use of Force Instructor. After retiring from the Brunswick Police Department as a Lieutenant, he worked at the Cumberland County Sheriff’s Office. At the rank of Captain, he oversaw the Support Services Division and then the Criminal Investigations Division. He is currently 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 teaching. 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. Over his 34 years of being in law enforcement, he has attended well over 2,405 hours of In-Service Training with an emphasis in Executive Leadership, Management, Police Operations, Employee and Instructor Development.

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.

“You are not here merely to make a living. You are here in order to enable the world to live more amply, with greater vision, with a finer spirit of hope and achievement. You are here to enrich the world, and you impoverish yourself if you forget the errand.” Woodrow Wilson

Instructor For


  • FBI National Academy Graduate Class #253
  • Bachelor's Degree In Business Management With A Minor In Human Resources
  • Associate Degree In Criminal Justice with 2,254 Hours Of In-Service Training


  • Strategic planning
  • Development of transition plans into command positions
  • Management of selection process from entry to command level positions
  • Municipal and federal budgeting, labor / human relations
  • Personnel Management
  • Career development

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