James Hart, the first employee at Asos alongside the two founding directors, has resigned after 14 years to pursue another career.
His departure comes after a year of management changes at the fashion etailer and emerges amid rumours the Asos board is paving the way for a listing in the FTSE 100.
Hart - who has no official title but describes himself as chief product director - has worked with chief executive Nick Robertson since graduating in 1996 and was the first employee at the business when it launched in 2000, working alongside Robertson's co-founder Quentin Griffiths.
His departure follows the short-lived tenure of Kate Bostock, the former Marks & Spencer womenswear boss who left in July after seven months, and head of human resources Michelle Emerson who left the same month.
More recently, Asos appointed another former Marks & Spencer executive Ian Dyson as a non-executive in August and, last month, is understood to have drafted in Amazon Europe's finance vice-president Shaun McCabe - as yet unconfirmed, but who is expected to become finance director.
The upheaval is understood to reflect a deep shift in the firm's strategic footing as it prepares for global growth to compete with European, Asian and American fashion giants in the etail sector. It is rumoured that Asos also wants to shift its listing from its current place on Aim to the FTSE which, with a market capitalsation of more than £4 billion would guarantee it a place in the FTSE 100 and dramatically shift its standing in the eyes of major investors.
Among the other senior changes have been the departure of long-serving product director Robert Bready and respected buying director Caren Downie, who left last year after Bostock's appointment. International director and former finance director Jon Kamaluddin left in April after nine years in the job.
Meanshile, Asos reorganised its buying teams last month which included the promotion of Maria Hollis to retail director and the creation of a number of other new roles. Simon Platts was also appointed souring director from JD Sports' outdoor business. Asos also appointed former Amazon UK managing director Brian McBride as chairman in October last year - replacing Lord Alli who had been at the firm since 2001.
Hart, who is on a six month contract, told trade magazine Drapers: 'I'm genuinely open to consider anything and and I'm leaving with enough time in my career to start something new.'
Hart said he would like 'to make a difference to the consumer... whether in a start-up environment or starting something on my own.'
It is not clear whether Hart will be replaced. His decision comes after a series of departures over the past 12 months that included the arrived and shock exit of former Marks & Spencer's womenswear boss Kate Bostock.
Departures from Asos in past 12 months:
James Hart, chief product director (September)
Michelle Emerson, head of human resources (July)
Kate Bostock, executive director product and trading (July)
Jon Kamaluddin, finance director (April)
Robert Bready, product director (October 2012)
Caren Downie, buying director (October 2012)
Lord Waheed Alli, chairman (Octoner 2012)
Arrivals:
Shaun McCabe, finance director (as yet unconfirmed)
Simon Platts, sourcing director (August)
Ian Dyson, non-executive director (August)
Kate Bostock, executive director product and trading (October 2012, subsequently left - see above)
Brian McBride, chairman (October 2012)
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