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Brad Woolf has a diverse work experience spanning over 25 years. Brad started their career in 1994 as a ParaTrooper in the California Army National Guard, which they served until 2003. Brad then worked at Intuit as a Systems Engineer/Architect from 1999 to 2005. Brad joined Northrop Grumman in 2005 as a Project Manager before moving to Symantec, Corp. in 2006, where they held roles as a Business Critical Account Manager and later as a Sr. Systems Engineer. In 2010, Brad worked as an Account Executive at Helixstorm, Inc. before transitioning to Bohica Associates as a Service Account Executive in 2011. Brad joined Oracle in 2012 as a Senior Sales Consultant and then moved to MapR Technologies in 2016, where they worked as a Solutions Engineer until 2018. Brad was then employed by Amazon Web Services (AWS) as a Solution Architect from 2018 to 2019. Currently, they are working at ClearDATA as a Sr. Solution Architect.

Brad Woolf's education history includes attending Excelsior University, although the specific years are not mentioned. Brad also obtained a Certificate in Project Management from The George Washington University School of Business. In addition to their formal education, Brad has several certifications related to Amazon Web Services. Brad obtained the AWS Solutions Architect Associate certification in June 2018, AWS Certified SysOps Administrator - Associate (SOA) certification in February 2019, and the Amazon Web Services Solutions Architect - Professional certification from Linux Academy in December 2019. Furthermore, Brad recently acquired the AWS Certified Security - Specialty certification from Amazon Web Services in December 2021.