As a red-and-blue-team member turned sysadmin herder, Bill Weiss had an early introduction to automation in security, and he's spent the rest of his career trying to bring that idea to more places. He started out working in the .gov, moved to Chicago to spend several years at a financial services SaaS, and finally made it to Portland in 2015 to join Puppet as the Manager of SysOps, which he thinks is a way better term than “sysadmin”.