A long-time lieutenant of Sir Philip Green’s has quit as a director of Arcadia, piling more pressure on the businessman as he looks to break up the group.

David Shepherd stood down from his role as chief operating officer of Arcadia at the end of last month, according to a filing at Companies House.

He had been with the business for 25 years, having begun his career there as a buyer before working his way up to oversee the running of Topman. He took on his most recent role in 2012.

The Telegraph also reports that “another resignation could be on the cards”, although it has yet to publish the identity of that person.

Shepherd’s departure comes at a difficult time for Green’s flagging fashion empire – which includes brands such as Topshop, Miss Selfridge, Burton and Dorothy Perkins.

Break-up

Green and Arcadia chief executive Ian Grabiner have begun the process of separating the different brands within the group in a bid to offload a number of them.

According to The Sunday Times, the idea was originally Grabiner’s, who convinced the fashion mogul that the group would not be able to trade its way out of the challenges it is facing.

However, the plan could yet be scuppered by The Pensions Regulator, which was something of a thorn in the side of Green during its company voluntary arrangement (CVA) proposal earlier in the year.

The regulator would be able to block any prospective plan due to the £750m deficit buyout in Arcadia’s retirement funds – £385m of which Green pledged to pay towards over the next three years as part of the agreed CVA deal.

The group is also reportedly trying to separate shared in-house functions such as IT and HR.

Arcadia secured its CVA on its second attempt in June, winning approval from creditors to close 23 stores and reduce rents on nearly 200 others, safeguarding 17,000 jobs.