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Doug Gillespie began their work experience in 1994 as a Senior Field Service Technician at Information Products, where they provided field support to clients in New Jersey. Doug initially supported HP LaserJet printers and various PC brands, later transitioning to software support.

In 1995, Doug joined Skandia America Group as a PC/LAN Support Specialist on a temporary basis. In this role, they supported a client base of 200 workstations and handled tasks such as Microsoft Office and Lotus software support, as well as Novell Netware administration.

Also in 1995, Doug joined Fusion as Vice President Systems. In this position, they led multiple teams, including software development, voice engineering, IT, and systems. Doug was responsible for managing an in-house carrier-grade hosted VOIP platform and overseeing Vmware clusters and voice platforms across multiple data centers.

Doug Gillespie attended Mendham High School. No information is provided about the start or end year, degree name, or field of study.