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Jack Sheehan has a diverse work experience in the landscaping and snowplowing industry. Jack started their career as a Foreman at Chris' Landscape, Inc. in 2004 and worked there until 2006. Jack then joined Apex Landscaping as an Operations Manager from 2007 to 2011.

In 2012, Jack joined Contour Landscaping Inc. / Snow & Ice Management as an Account Manager, and they held this position until 2014. Jack then moved to Tim's Snowplowing Inc. as an Account Manager from 2014 to 2015.

Since 2015, Jack has been associated with Aero Operating LLC and Family of Companies. Jack started as an Operations Manager and later became a General Manager in 2018. Currently, they hold the position of Regional Director of Operations.

Jack Sheehan attended the University of Illinois Urbana-Champaign from 1995 to 1999. However, no information is provided regarding the degree obtained or the field of study. In addition to their education, they obtained the Illinois Pesticide License from the State of Illinois Department of Agriculture in March 2012. Jack also earned the Certified Landscape Technician certification from Planet/ILCA in August 2008.