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Jim Stott started their career in 1995 as a Group Underwriter at Sun Life Financial. Jim then worked as a Marketing Assistant at Jefferson Pilot Financial from 2002 to 2005. From 2005 to 2006, they were a Sales Representative at Guardian Life Insurance. Jim then joined Assurant Employee Benefits as a Sales Representative from 2006 to 2008 and later worked as a Sales Representative at Standard Insurance Company from 2008 to 2012. In 2012, they became a Senior Employee Benefits Sales Representative at Sun Life Financial until 2014. Jim then worked as an Account Executive at Liazon from 2014 to 2015. From 2015 to 2018, they held the positions of Vice President of Operations and later Senior Vice President of Operations at EBS, Employee Benefit Solutions.

Jim Stott attended Marlborough High School from 1987 to 1991. After completing high school, they went on to pursue a Bachelor of Science (BS) degree in Management from Bentley University, which they obtained between 1991 and 1995.