Pressler, Gap's CEO since September 2002, will receive a severance package valued at $14 million as he walks away from the turmoil that has raised questions about the company's future.
The San Francisco-based company, which owns 3,100 stores under the Gap, Old Navy and Banana Republic brands, has been mired in a sales funk since the spring of 2004.
As it became increasingly apparent that things weren't improving, more investors became convinced Pressler would be ousted. In a Monday statement, Gap said its board and Pressler "mutally agreed" it was time for him to leave.
Gap named Robert J. Fisher, the son of founder Donald Fisher, as CEO on an interim basis. The younger Fisher has previously held several top jobs at Gap and has been the company's nonexecutive chairman since May 2004 when he stepped into the shoes of his father, who remains the retailer's largest shareholder and will participate in the search for a new CEO.
After Gap's latest letdown during the holidays, more investors began to bet that the company would be sold to a deep-pocketed buyout firm interested in engineering a turnaround.
The speculation intensified earlier this month amid reports that Gap had hired investment firm Goldman Sachs to explore "strategic alternatives" financial jargon often used when companies are about to throw out a "for sale" sign.
The shake-up could signal Gap's intention to remain independent. Given Gap's problems and the estimated $20 billion sale price, several analysts doubted the company's ability to attract a buyer.
In a statement issued Monday, Robert Fisher made it sound as if Gap will try to fix its problems on its own.
"During this important transition period for our company, the board of directors and I are committed to working with our employees to enhance our focus on what has been at the heart of the company's past success, reinvigorating our brands and charting a new course for the future that will deliver strong returns for our shareholders," he said.
The Fishers hold the key to any possible sale because they own more than 25 percent of the company's stock.
Gap shares fell 10 cents to close at $19.90 on the New York Stock Exchange, then gained 53 cents in extended trading after Pressler's departure was announced.
The elderly Fisher recruited Pressler from Walt Disney Co. the last time Gap was mired in a deep slump.
Gap bounced back during Pressler's first 18 months on the job, and he won high marks for closing poorly performing stores and instilling more financial discipline. But he never demonstrated a great deal of fashion sense or the ability to hire people who did a shortcoming that damaged Gap's brand as more shoppers defected to merchants that offered more hip choices or lower prices.
"The back end of the house was something that Paul did a phenomenal job," said Bobbie Lenga, managing director of the retail practice at executive recruiter Russell Reynolds Associates. "But he is not a strong product person. Product is what drives the business."
Lenga expects Gap to have a tough time finding a dynamic new leader because turning around the company will be an extraordinarily difficult assignment.
Coming off a lackluster 2005, Pressler vowed to turn things around in 2006 and projected earnings in the same range as the previous year.
Instead, Gap's deterioration worsened as the year progressed, prompting Pressler to lower his earnings guidance three times.
The final straw apparently came earlier this month when Pressler warned that Gap's profit for fiscal 2006 will end up about $300 million, or 40 cents per share, below the target he set at the year's outset.