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Sherry Lees has over 25 years of work experience. Sherry started their career as an Audit Senior at Price Waterhouse in 1992. Afterward, they worked at Agricore United, holding various positions such as Senior Financial Analyst, Controller Crop Production Services Division, and Corporate Treasurer. In 2009, they became the VP of Finance at Interlake Regional Health Authority. In 2010, they joined Parrish & Heimbecker Ltd as a Corporate Controller and later became the VP of Finance in 2017.

Sherry Lees completed their Bachelor of Commerce degree in Accounting from the University of Manitoba between 1988 and 1992. Following this, they attended the Institute of Chartered Accountants of Manitoba from 1992 to 1994, where they obtained the degree of Chartered Accountant. No specific details were provided regarding their field of study during their time at the Institute of Chartered Accountants of Manitoba.