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Dave Oakman has extensive work experience in the technology industry. Dave started their career as an Inside Sales representative at Radio Shack Computer Center in 1986. In 1989, they became a Network Engineer at Connolly Data/CTG/Ameridata, where they worked until 1995. From 1995 to 1998, Oakman served as the Manager of Technical Services at Gilbane Building Company. In 1998, they joined Carousel Industries as a Technical Director, a role they held until 2011. At Carousel Industries, Oakman later served as the Director of Innovation from 2013 to 2015, and as the Chief Engineer from 2015 to 2016. Dave then returned to their role as Chief Engineer at Carousel Industries in 2017, leading the team of Technical Directors in infrastructure practices and supporting business innovation initiatives.

Dave Oakman completed their Bachelor of Science degree in Management Information Systems (MIS) from the University of Massachusetts Lowell from 1989 to 1992. Prior to that, they pursued Computer Science at the Rochester Institute of Technology from 1986 to 1989, although they did not obtain a degree in this field. In terms of certifications, Dave obtained the Certified Cisco Systems Instructor (CCSI) accreditation from Cisco in March 2009, followed by the VMware Certified Professional (VCP) certification from VMware in February 2009. Additionally, they achieved the Cisco Certified Internetworking Expert (CCIE) Routing and Switching certification from Cisco in September 1999.