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Cholly Boland is the current CEO at Winchester District Memorial Hospital. Prior to this, they were a consultant for business management and healthcare from April 2011 to September 2011. From September 2008 to March 2011, they were the President and Chief Executive Officer at Headwaters Health Care Centre. From December 2003 to August 2008, they were the Chief Executive Officer at Arnprior Hospital/Grove Nursing Home. From April 2001 to December 2003, they were the CEO/Health Services Administrator at Kitimat Health Council/Northern Health. From May 1997 to April 2001, they were the CEO at Community Care Access Centre Timiskaming.

Cholly Boland has an MBA and MHA from the University of Ottawa / Université d'Ottawa, and a B. Sc. in Engineering from Queen's University. Cholly also attended Harvard University for both their undergraduate and graduate studies.

Some direct reports include Lori-Anne Vanmoorsel - Executive Assistant, Medical Affairs, Brian Devin - Chief of Staff, and Michelle Blouin - VP, Corporate Services & CFO.