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Stephen McKinnon has an extensive work experience, beginning in 2004 with The Law Offices of McKinnon & Harwood as an Associate Attorney. Stephen then moved on to Unum in 2007 as an M.B.A. Intern and was a direct report to the Vice President of the Unum Contact Center. In 2009, they joined Amica Mutual Insurance as a Sr. Business Process Analyst, and later was promoted to Sr. Account Manager and Account Manager. In 2014, Stephen began working at NLC Insurance Companies as a Business Process Manager, a role in which they were a direct report of the Chief Underwriting Officer and managed the business lead for NLC's Guidewire policy administration system replacement project. Most recently, in 2021, Stephen joined Proof Authentication as Vice President of Client Solutions.

Stephen McKinnon obtained their High School Diploma from Moses Brown School in 1997. Stephen then attended Bowdoin College from 1997 to 2001, where they earned their B.A. in Psychology. Following that, they attended Villanova University Charles Widger School of Law from 2001 to 2004, where they earned their J.D. in Law. Finally, they attended Boston College Carroll School of Management from 2006 to 2008, where they earned their M.B.A. in Business Administration.