More and more on Hillary's emails?

Hillary Clinton was revealed to have used personal e-mail to conduct U.S. foreign policy while she was Secretary of State. She was speaking at Emily's List on Tuesday when a blonde in the audience heckled her about it. The blonde was hustled outside by security where Bill Clinton wrestled her to the ground. Comedian Argus Hamilton

 Secrets of Clinton emails revealed   . . . "Hothem is the same aide who was charged with packing up and carting off furniture from the White House at the end of Bill Clinton's presidency that he said was 'Clinton’s personal property.' 

Was the State Department 'IT guy' Asleep at the Switch?     "Beyond the legal stuff, there are lots of red flags or things that jump at me:  

1) Where was the "IT guy" at the State Department? Did he or she know that the Secretary of State, a person writing and reading about sensitive information, waa not using an official email?   
2) If yes, who did he or she talk to about it? Was some supervisor alerted? How high up the chain did this alert go?  Was President Obama alerted to the incredible risk of having the country's top diplomat doing the nation's business on a private server?
3) If no, then are these the same people who put together the ObamaCare website?