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Jim Strickland has a strong work experience in the technology industry. Jim started their career in 1999 at Mosaik Solutions, where they held various roles, including IT Director and Director of Systems & Physical Plant. In these positions, they were responsible for maintaining the network, computer systems, and servers, as well as developing new products and services. In 2011, American Roamer split its IT department into separate entities, and Jim took on the role of Director of Systems. Jim continued in this role until 2023. In 2018, they joined Ookla as Director of Systems & Physical Plant, and later became the Director of Operations.

Jim Strickland attended Christian Brothers University from 1987 to 1989, where they studied Biology. Jim then went on to enroll at The University of Memphis from 1989 to 1992, majoring in Anthropology. In addition to their formal education, Jim obtained several certifications, including the "Servant Leadership Online Journey" from the Greenleaf Center for Servant Leadership in October 2019, the "Nimble Introduction and Administration" from Nimble Storage in September 2016, and the "Salesforce Certified Administrator" from Salesforce in February 2014.