During his career Ian Comfort has been a maths teacher, a leader of the London local authority and has combined this with active work as a barrister of the Inner Temple. In 2012 he became the CEO of Academies Enterprise Trust, which at that time was the largest Multi-Academy Trust in England. Prior to joining AET (Academies Enterprise Trust) in 2009, Ian Comfort, was the Chief Executive of Edutrust, a Multi-academy Trust which was renamed as E-ACT in 2010. Ian left E-ACT (now called Edutrust Academies Charitable Trust) under controversial circumstances. His contract was ended amidst Trust accusations of 'poor performance' whilst he himself counter-claimed that he was being victimised for being a whistleblower. The case was settled out of court for an undisclosed sum, following a significant period of being at home on full salary.
Ian Comfort began his teaching career as a Maths teacher and progressed to become a Director of a Local Education Authority before becoming the Chief Operating Officer for the Ark Academies Chain Joining AET in 2009 Ian Comfort was initially Group Secretary and General Counsel. Following the retirement of David Triggs, the previous CEO in Sept 2013, AET posted the notice of Ian Comfort's appointment as interim CEO on 2 April 2014. Shortly after Unity City Academy had been OFSTED graded down from good to Inadequate it was announced via press release at AET Mr Comfort is to leave in the Spring Term 2017 to be replaced by Julian Drinkall formerly CEO of the Alpha-Plus Group.
As CEO of Academies Enterprise Trust Ian Comfort is also CEO of London Academies Enterprise Trust which is a subsidiary trust within the AET family, containing 4 secondary schools.
In June 2015 Ian Comfort was reported as earning £220,000 per annum, which was the second highest pay of CEOs in England leading Multi-Academy Trusts In 2013 concerns were expressed nationally about the fact that he had received £329,000 in addition to his salary for "project management services". This contributed to criticism of the Department for Education for allowing "related party payments" within Academy Trusts.
By March 2016 Sir Michael Wilshaw, the head of OFSTED, was criticising excessive salaries for CEO's of Academy chains as a "poor use of public money" referring to Ian Comfort's salary by stating that "Given these worrying findings about the performance of disadvantaged pupils and the lack of leadership capacity and strategic oversight by trustees, salary levels for the chief executives of some of these MATs do not appear to be commensurate with the level of performance of their trusts or constituent academies, with one chief executive's salary reaching £225,000." Dia Chakravarty, from the TaxPayers' Alliance stated "Taxpayers don't begrudge just rewards for good results but far too often taxpayer-funded salaries are handed out to fat cats irrespective of performance. Parents will want to keep a very close eye to make sure that it really is good value for money." Dr Mary Bousted, general secretary of the Association of Teachers and Lecturers (ATL), said: ‘It is becoming increasingly difficult for some academies to justify paying their chief executives and heads such high salaries.
In September 2014 Ian Comfort announced a downsizing of the Academy chain, which saw it reduce from 77 Academies to 68. In the summer of 2014 Ian Comfort led a proposal for a Joint Venture with a for-profit business partner, which would have led to the largest outsourcing of school services within England. Following a letter of concerns on 10 Jun 2014, from 8 main teaching unions, the proposal was dropped.
During his career with AET Ian Comfort has led the organisation through a period of controversies. In 2014 there was an OFSTED inspection which accused the Academy chain of having low expectations and failing its pupils. Ian Comfort robustly denied those findings and AET "criticised inspectors' findings as "unfairly negative" and (said) that "turning a school around takes time"". However, when OFSTED returned to reinspect the chain, this led to a further report criticising AET in February 2016, for "medicore performance" and for still "failing too many of its pupils." This "damning indictment" and "sharp rebuke" as the national press referred to it, was once again rejected by AET as "unfair". Ian Comfort disagreed and explicitly rejected OFSTED's views and was reported as stating that "In all areas we are performing above the national average." Unfortunately AET's own board minutes showed that its proportion of pupils achieving the key government milestone of 5GCSEs A-C grades (including English and Maths) was 43% in 2015, compared to a national average of 56%, meaning that AET was therefore 13% below the national average. It was also noted by the Times Education Supplement, that far from standards within AET schools being "above the national average," the situation "has become so serious that representatives from the Department for Education now sit in on the trust’s board meetings"
Under Ian Comfort's leadership AET also was involved in controversy about why the academy chain shrank in size. It has been claimed in the press that it was because the academy chain had expanded too fast and Christine Blower the head of the NUT stated “It is obvious that AET’s rate and scale of expansion was unsustainable and that it is unable to adequately support its schools." However AET denied that it had been 'banned' from expanding and insisted that it had instead chosen to "pause and consolidate".
In 2015 Ian Comfort also directly contradicted the Government (DfE's) claim that Academy status creates extra freedoms for headteachers, by claiming that headteachers of Academies had significantly less freedom than headteachers of non-academies.
In June 2015 Ian Comfort met with Sir George Young, the Hampshire MP to discuss concerns about school improvement at Winton Community Academy In October 2015 Sir David Carter wrote a public letter to Ian Comfort warning about the unacceptably low standards at Millbrook Academy, a secondary school within the Academies Enterprise Trust group. On the Isle of Wight, low pupil numbers following the decline of Weston Primary school into Special Measures, meant that the school had to be closed. Ian Comfort led the closure commenting publicly on how sad it was, but that it was no longer possible to provide the quality of education which pupils deserve, when numbers had dropped so low.
In the spring of 2015, following a campaign led by MP Priti Patel, Ian Comfort announced that AET would no longer be considering merging the Academies in Witham. In the summer of 2015 Ian Comfort also made national news by announcing that Academy Principals within AET have less freedom than headteachers of maintained non-academy schools.