Whoever takes over at the helm of a Lincolnshire education empire will have to have "started their career in the classroom", say experts.
Next week, governors at Lincoln's Priory Federation of Academies Trust will begin looking to appoint a new chief executive.
It follows the resignation of Richard Gilliland at lunchtime on Friday, March 30, just hours before schools were dismissed for the Easter break.
The successful candidate will oversee the running of four schools – The Priory Academy LSST, The Priory Witham Academy, The Priory City of Lincoln Academy and The Priory Ruskin Academy.
They will also be in charge of a riding school in the south of the county and an educational centre in France.
It is understood that the job commands a six-figure salary.
The trust was formed in September 2008. Mr Gilliland, who was previously headteacher at LSST, took on the role of chief executive from the start.
During his tenure, Mr Gilliland has overseen developments such as a £26 million building project at the City of Lincoln Academy, the opening of the Laughton Manor Equestrian Centre near Sleaford and the £1.8 million Centre des Etoiles, based in France.
Deputy chief executive Ian Jones has taken over the role on an interim basis.
Mike Barnett, spokesman for the Academies Enterprise Trust, a network for academy schools, said that he believed a replacement candidate would have to come from a similar background with experience in the classroom.
He said: "Most of the current leaders of academies began in the classroom before moving up the ladder to become headteachers or principals.
"A number may have been asked to link up with other schools in order to give them a helping hand. They therefore become adept at thinking outside the school and supporting others.
"First and foremost, chief executives need to be leaders in education.
"The budgets may run into the millions and millions but that is where accountants and people with financial experience will be able to support the organisation."
Ormiston Academies Trust, which includes schools across the UK, is coming to the end of the recruitment process for a new chief executive.
Kris Griffin, head of marketing and communications for the trust, said: "We made the recruitment process completely open and engaging and for us that was vitally important.
"At the heart of our trust there are 14,500 students and it's important that every decision we have made is always centred around them. It just has to be."
As reported on the Echo's sister website thisislincolnshire.co.uk Mr Gilliland has cited "personal reasons" for his resignation. Despite repeated requests from the Echo, the trust nor its board of directors would comment further.
Lincolnshire County Council also refused to comment on the resignation of Mr Gilliland.
Chairman of the trust, Terry Coffey, said: "We would like to acknowledge everything that he has achieved during his career."