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Paul Rakowski began their work experience in 2009 as a lawyer at Stikeman Elliott LLP. Paul held this position until August 2017. In September 2017, they transitioned to the role of Vice President and General Counsel at CareRx Corporation. Paul Rakowski then became the Senior Vice President of Corporate Development & General Counsel in May 2021.

Paul Rakowski obtained an MBA from the Schulich School of Business at York University from 2005 to 2008. Paul also earned a JD from Osgoode Hall Law School, completing their studies from 2004 to 2008. In addition, Paul Rakowski pursued a certification in the CareRx Pharmacy Manager Leadership Development Program at The Ivey Academy at Ivey Business School. The year in which they obtained this certification is not specified.