Microsoft paid 'more than £1million' to silence a female executive who was unfairly overlooked for the role of UK managing director at the firm.
Natalie Ayres, a married mother, missed out on the job in the summer of 2006, despite being considered a shoo-in.
Instead it was handed to Gordon Frazer, a general manager at Microsoft South Africa, allegedly before Mrs Ayres had even finished the interview process.
Mrs Ayres, a talented Microsoft employee of 15 years, left at the end of the year with a 'compromise agreement' that ran into seven figures, Microsoft sources revealed in the Daily Telegraph today.
'It's a boys' club,' said one. 'The only way to progress beyond a certain point is to become a male in female clothing.
'They [management] do not follow procedure enough and if your face doesn't fit, you suffer.'
Mr Frazer, who succeeded Alistair Baker as MD of Microsoft UK, said at the time that Microsoft would miss her 'dedication and intelligence' but respected her 'personal decision to move on'.
Mrs Ayres - general manager of the company's Small-Medium Enterprises & Partners Group in the UK - is quoted on the diversity section of the Microsoft website as having said in the past that the company is a good place for women to work.
'Women can be more susceptible to self-doubt, but I've always found a natural place at the table for me at Microsoft at every level,' she says.
But the source said that women tend to hit a glass ceiling at the computer company in more senior roles of 'level 65 or above'.
It is only the latest episode in a series of embarrassing revelations about life at Bill Gates's firm.
Earlier this month, several stories emerged of sexual harassment by married male senior managers of female colleagues.
Claims of heavy drinking and unwanted advances from executives at a raucous Microsoft party in the US are to be laid bare in a £10million High Court battle.
The court case centres on Simon Negus, 50, a married man from Pirbright, Surrey, who worked as UK general manager for Microsoft and was dismissed last year.
A High Court writ issued by Microsoft claims Mr Negus kissed a colleague at the American party in 2009 before asking another to ‘flutter her eyelashes’ and a third to stand on a chair so partygoers could examine her short skirt.
Mr Negus denies the claims and is counter-suing the computer firm for harassment, loss of earnings and wrongful dismissal.
A spokesman for Microsoft said: 'As is standard practice for any responsible company, Microsoft does not comment about individual employees – current or former. However, Microsoft places great importance on our core values of diversity and inclusion which is just one of many reasons why we are consistently ranked as one of the top 50 best workplaces in the UK.'
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