What lies in store for one of the more acquisitive tech giants as it matures and struggles through a major evolution in search of growth? Despite the revolving CEO door at HP's Hanover Street headquarters in Palo Alto, Calif., the company's acquisitiveness has been relatively consistent over its recent history. That said, over the past year it has been willing to pay very high multiples to enter new markets with splashy deals. Its high-stakes bidding war last year for storage technology maker 3Par Inc. was viewed as undisciplined, and its pending $10.8 billion deal for data management software maker Autonomy Corp. plc is seen as overpriced.

It's a bit early to tell what happens now that 55-year-old Whitman, the former eBay Inc. chief and unsuccessful California gubernatorial candidate, is running the show. Whitman does have a good amount of acquisition experience under her belt, having overseen about 26 transactions worth $6.7 billion in aggregate. Her two largest transactions are worth a look; one's a huge winner and the other a big loser.

Arguably the best deal ever made by eBay -- and one that routinely makes top 10 lists of technology acquisitions -- is its 2002 acquisition of online payments system provider PayPal. EBay paid $1.5 billion to buy the leader in its space in a bid to simplify what eBay enables -- buying and selling goods online.

As one observer puts it, the deal was a no-brainer, and now PayPal is a flourishing $3.4 billion business.

Then there's Skype Technologies SA. Bought in October 2005 for $2.6 billion, the strategy behind eBay's purchase of the Internet phone service provider was nowhere near as clear as it was in the PayPal purchase. The deal didn't gel, eBay took a $1.4 billion write-down charge in 2007 and sold a majority of the company to a private equity consortium led by Silver Lake last year for $1.9 billion and a $125 million note. (The PE group did considerably better with Skype, striking an agreement in May to sell it to Microsoft Corp. for $8.5 billion.)

The Skype failure is considered a key reason Whitman was replaced in April 2008 by John Donahoe, who started mulling an exit strategy from the deal as soon as he landed at eBay.

Certainly, acquisitions will be part of HP's growth strategy going forward, though the company is likely to keep a relatively low profile in M&A. Whitman will need to settle in and figure out whether to keep or spin off HP's PC division. The company still has to close and digest the pending, high-multiple purchase of Autonomy, which, in her first public comments Sept. 22, the CEO supported as a part of HP's evolution. Analysts hope that Whitman will continue HP's push into software, as well as services and cloud computing, but also want her to rein in the company's recent willingness to pay exorbitant sums.

"People understand why HP is buying Autonomy, but it's the price they are uncomfortable with," says Sterne, Agee & Leach Inc. analyst Shaw Wu.

Beyond her M&A acumen, there are nagging concerns that Whitman's experience at eBay and earlier in her career leave the CEO ill prepared to fix HP, which is huge, complex and enterprise-focused. There's no arguing that overall Whitman was successful at eBay, growing what was a tiny three-year-old startup when she joined in 1998 into an $8 billion Internet giant by the time she left.

But her "company-fixing" credentials are questionable. Her only prior CEO job was as head of flower delivery company F.T.D. in the mid-1990s. She quit after two years over what she described as unrealistic investor expectations, calling the company "not fixable, at least by me," in her 2010 book "The Power of Many."

Whitman is not remembered with any particular fondness by many within eBay today. Sure, company headquarters in San Jose, Calif., are still called the Whitman Campus. But during her final years at the company, the wave of success subsided, and Whitman was criticized for being an aloof leader who continued to take large bonuses even as the company faced financial challenges. "By the time she left eBay, she had run the motorboat dry," an eBay executive says. "We were close to empty on strategy, and she used company resources in a way that wasn't helpful in the long term."

This eBay executive, who spoke on condition of anonymity, also notes that when Whitman was running for California governor, there were "zero signs of support for her on campus. People here are much happier with Donahoe."

Donahoe gets fired up when meeting with his troops, often dropping the f-bomb and urging workers to "kick ass" as part of his full-tilt management style. Whitman was sometimes criticized as being standoffish.

How much this matters is debatable. What is clear, however, is that Whitman is taking on what is likely the biggest professional challenge of her career, running a giant, enterprise-focused company in the midst of a transition that will likely be continually hastened by acquisitions. Good luck.