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Craig MacInnis has a diverse work experience spanning several industries. Craig currently serves as a Board Director at OntarioMD, a position they have held since May 2023. Prior to this, they co-founded myCaribou in February 2020. Craig also worked as an Advisor at Recurring Capital Partners and SafetySkills starting in November 2017. Additionally, Craig has volunteered at GiGi's Playhouse Inc.- Down Syndrome Achievement Centers since January 2020. Earlier in their career, they were an Advisor at TemboSocial from January 2018 to November 2019. Before that, they were Senior Vice President and General Manager at Upland Software from November 2014 to November 2016. Craig was the CEO and Founding Partner at Solution Q Inc. from February 2002 to November 2014. Prior to that, they served as President and CEO at Knowledge Alliance Inc. from April 2000 to February 2002. Craig started their career at Knowledge Alliance Inc. in 1991 and held various positions including Sales Manager, Branch Manager, and Vice President until 2000.

Craig MacInnis completed their BA in Economics at Western University between 1988 and 1991. Craig later pursued an MBA in Marketing and Finance at the Schulich School of Business - York University from 1997 to 2002.