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John Gillespie has a diverse work experience spanning over several decades. John began their career at Plantronics in 1989, where they held various roles, including Senior Territory Manager, Senior Manager of Unified Communications, Senior Manager of Strategic Alliances, and finally Director of Global Consulting & Alliance Accounts. John worked at Plantronics until 2019.

In 2019, Gillespie joined Poly as the Director of Global Consulting and Strategic Alliances. John worked with Poly for a year, until 2020.

In 2021, Gillespie joined DataMotion, Inc. as the Senior Director of Business Development and Partner Management. John is currently serving in this role.

John Gillespie pursued their education at Rutgers University, where they completed a Bachelor's degree in Business Administration from 1977 to 1981. In 2005, they also attended Rutgers University–New Brunswick and obtained a Mini-MBA through the Business Essentials Program. Additionally, John obtained a Certification of Achievement in Alliance Management from the Association of Strategic Alliance Professionals in October 2019.