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Tim Lesser has a diverse work experience spanning over several companies. Tim started their career as a Hunting Guide at Wyoming Professional Hunters, Ltd. in 1997, where they worked until 2009. In 2004, they established their own company, Wyoming High Plains Safaris, LLC, which they ran until 2008.

In 2003, Lesser joined Leupold & Stevens, Inc. and held various roles, including Technical Service/Custom Shop Lead, Marketing Communications Specialist, Product Line Developer, Category Manager, and Brand Manager. Tim'stenure at Leupold & Stevens, Inc. ended in 2013.

From 2013 to 2014, they served as the Vice President of Sales and Marketing at The Sharps Rifle Company. In 2014, they returned to Leupold & Stevens, Inc. as the Director of Product Development, and later became the Vice President of Product Development. In 2022, Lesser took on the additional role of Vice President of Product Development & Marketing at Leupold + Stevens, Inc.

Tim Lesser completed their Bachelor of Arts degree in Elementary Education from the University of Wyoming in the years 1997 to 2000. Following this, they pursued further education and obtained a Master of Education (M.Ed.) degree in Curriculum and Instruction from the University of Montana from 2001 to 2002.