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Shawn O'Leary started his career as a summer Reserve Officer for the Towns of Ogunquit and Wells. In 1988 he was selected by the Brunswick Police Department where he eventually retired as a Patrol Lieutenant. During his tenure, he was the Primary Use of Force Instructor, oversaw all background investigations, managed numerous federal and state grants, was a member of the Special Response Team and Bike Patrol Unit. After retiring, he worked initially as the Captain of Support Services for the Cumberland County Sheriff's Office and later oversaw the Criminal Investigations Division. Currently, he is the Chief of Police for the Town of Winslow.  


During his 32 years in Law Enforcement, fourteen of them have been at the Supervisory or Command level. He has had a diverse career, allowing him to teach at the Maine Criminal Justice Academy, Maine Chief of Police Traveling Road Show, and at other various venues throughout the state.  His professional skills entail a  strong leadership philosophy towards mentoring, teaching, motivating and developing cohesive teams to fulfill the needs of the individual, agency, and the community officers serve. Additionally, he has a strong management background to include organizational assessments, strategic planning, policy development, budgeting, innovations, and implementation of identified goals.  


Shawn has an Associates Degree in Criminal Justice from Bangor Community College, a Bachelors Degree with honors in Business Management with a minor in Human Resource Management from Southern New Hampshire University, and he is a Graduate of the FBI National Academy Session 253. Additionally, over 2,254 hours of In-service training with an emphasis in Executive Leadership, Operations, Use of Force and Instructor Development.  

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