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Robert McKendry has had a diverse range of work experience. Robert started their career in 2001 at Best Buy as a Media/Merchandise Manager, where they were responsible for leading the biggest department in the store and the district. Robert then moved on to Toys R Us as a Front End/Sales Manager, overseeing various operational areas and ensuring efficient store operations.

In 2006, McKendry joined Family Dollar as a Store Manager, where they maintained inventories, store appearance, and provided exceptional customer service. Robert later joined PLS Financial Services in 2008 as a Store Manager, focusing on daily operations, team building, and superior customer service.

McKendry then transitioned to Telkonet Inc. in 2013, first serving as a Technical Customer Service Agent (TCSA) 3, where they acted as the primary point of contact for customer issues and assisted in troubleshooting and resolving tech problems. Robert later became a Project Manager, responsible for project execution, developing schedules, and ensuring customer expectations were met.

Throughout their career, McKendry has demonstrated strong leadership skills, customer service expertise, and a commitment to team development.

Robert McKendry attended the University of Wisconsin-Milwaukee from 1990 to 1995. Their major was Health Care Administration, and they minored in Business, graduating in 1996. In 2012, they attended Brensten and obtained vocational certifications in Information Technology. Robert also received additional certifications during that time, including "98-365: MTA: Windows Server Administration Fundamentals" and "98-349: MTA: Windows Operating System Fundamentals" from Microsoft, as well as "98-366: MTA: Networking Fundamentals" and "CompTIA Strata IT Fundamentals (FC0-U41)" from CompTIA.