||Special Adviser to Michael Gove (2007–2014)
Cummings worked for Conservative politician Michael Gove in various roles in opposition and government from 2007 to 2014. From February 2011 to January 2014 he was special adviser (spad) and Chief of Staff to Gove at the Department for Education (DfE). His appointment was initially blocked by Andy Coulson from 2010 until January 2011. Cummings was later appointed in February 2011 after Coulson's resignation. In this capacity, Cummings wrote an essay titled "Some thoughts on education and political priorities", about transforming Britain into a "meritocratic technopolis"; the essay was described by Guardian journalist Patrick Wintour as "either mad, bad or brilliant – and probably a bit of all three".
At the DfE, Cummings became known for his blunt style and "not suffering fools gladly"; he railed against the "blob", the informal alliance of senior civil servants and teachers who, in Cummings's opinion, sought to frustrate his attempts at reform. Cummings was also outspoken regarding other senior politicians, describing Nick Clegg's proposals on free school meals as "Dreamed up on the back of a cigarette packet", and David Davis as "thick as mince" and "lazy as a toad". Patrick Wintour described the Cummings–Gove working relationship: "Gove, polite to a fault, would often feign ignorance of his adviser's methods, but knew full well the dark arts that Cummings deployed to get his master's way". At the Department for Education, Cummings was suspected[according to whom?] of leading a briefing campaign against the Home Office led by Theresa May and clashed with Cameron. In 2014, Prime Minister David Cameron, at a Policy Exchange speech in 2014 mentioned a "career psychopath", which was interpreted by several media outlets as a reference to Cummings, although the two had never met.
In 2012, a senior female civil servant received a payout of £25,000 in a bullying case she took against Cummings and a senior member of Michael Gove's team, when Cummings was a special adviser at the Department for Education.
During his time as an official working for Gove, Cummings received a warning from the Information Commissioner's Office (ICO) for use of private Gmail accounts to deal with government business, saying it should be 'actively discouraged'.[better source needed] The ICO uncovered an email from Cummings in which he said: 'i will not answer any further emails to my official DfE account or from conservatives.com – i will only answer things that come from Gmail accounts from people who I know who they are' [sic]. Cummings said that this referred to the Conservative party conference, not government business.
In 2014, Cummings left his job as a special adviser and noted that he might endeavour to open a free school. He had previously worked for the New Schools Network charity that advises free schools, as a volunteer from June 2009 and then as a paid freelancer from July to December 2010.