Yahoo! yesterday fuelled speculation of a deepening boardroom split over its future direction when it lost another high-profile member of its management team.
The Silicon Valley-based company said that vice-president of business operations Anil Singh, the man widely credited with building its crucial advertising and marketing platform, was retiring "to spend more time with his family".
Mr Singh's departure is likely to increase the sense of crisis at the internet portal which last week surprised investors by announcing a profits warning and the resignation of its chief executive, Tim Koogle.
Advertising and marketing accounts for about 90% of revenues at Yahoo! and Mr Singh's departure is likely to be as keenly felt as the recent resignations of the heads at its European, Asian, South Korean and Canadian operations.
"Under [Mr Singh's] leadership the company built a top sales organisation from the ground up and pioneered the concept of online advertising," chief operating officer Jeff Mallett said.
Yahoo!, which was once valued at more than $100bn (£69bn), is now worth less than $10bn and has come to symbolise the boom and bust of the dot.com cycle.
Advertising revenues are now on the wane as advertisers, cautious of a slowing economy, rein in spending. Yahoo! has been unable to find other ways of making money out of its 185m users and for the first time since the fourth quarter of 1996 it is unlikely to turn a profit.
Merrill Lynch said it expected the online advertising market to decline 25% this year and for Yahoo's market share to drop from about 16% to 11% in 2001.
Analysts believe that it could now be forced to sell up to an older, established media company, in a move that would raise questions about the long-term survival of even the strongest of internet brands.
Viacom, Vivendi-Universal and Disney have all been mooted as possible buyers of Yahoo! but several of the portal's senior board members are thought to be against any takeover. Reports suggest they would prefer to introduce some form of subscription fee that would charge users for accessing content that is currently free.
AOL, Yahoo's biggest rival, last year stunned the financial markets by agreeing a "merger of equals" with Time Warner. That deal has given AOL access to a wide range of revenue streams that Yahoo! has little chance of emulating as a stand-alone business.
Mr Singh was Yahoo's 21st employee, joining in 1995 what was then a fledgling firm. He was the first sales executive but rose through the ranks and eventually became chief sales and marketing officer with responsibility for worldwide ad sales, corporate marketing, promotions, direct marketing and distribution.
Three months ago the company indicated that he would move from his day-to-day sales role to focus on strategy but in May he will leave the company altogether.
