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Jamie Macdonald has a diverse work experience spanning various sales roles. They began their career in 2003 as a National Accounts Manager at The Empire Company, followed by a position as an Inside Sales Manager at Metrie from 2005-2008. Then, they worked as a Sales Rep at Tingue, Brown & Company from 2009-2012. In 2013, Jamie joined MCMAHON & COMPANY as a Sales Representative, and stayed there until 2018. From 2018-2022, they worked as a Territory Manager at Fiberon Decking. Currently, Jamie holds a position as a Regional Sales at Northern Crossarm Co which they started in 2022. Jamie also has experience as a Partner at Midwest Sports Classics, a role that they have held since 2011.

Jamie Macdonald completed a Bachelor of Science degree in Sports Business from Northern Illinois University. They attended NIU from 1993 to 1998. In addition, Jamie obtained several certifications in various subjects from LinkedIn, including "Holding Yourself Accountable," "How to Be a Positive Leader (Blinkist Summary)," "Improving Your Listening Skills," and "Soft Skills for Sales Professionals." These certifications were obtained in 2020, with "Soft Skills for Sales Professionals" obtained in April and the rest obtained in May.