How did BoomTown forget former Autodesk exec Carol Bartz for Yahoo CEO?

Yahoo certainly hasn’t. According to several sources familiar with the Yahoo (YHOO) search for a new leader to replace Co-founder Jerry Yang, the company is looking hard at the longtime and high-profile Silicon Valley executive (pictured here).

Many I have spoken to inside and outside of Yahoo with knowledge of situation said the company is winnowing down its list to a few internal and external candidates and Bartz is a favorite.

While some speculate that Yahoo could announce a candidate sooner than later, it’s long past when Yahoo Chairman Roy Bostock promised some big investors a new and serious leader would be in place.

Some sources close to the board still think Yahoo could still end up opting for one of its own.

If so, the leading choice is most likely board member John Chapple, former Nextel CEO, although sources say he does not want the post now, preferring an outsider for Yahoo CEO. The other board member mentioned is Maggie Wilderotter, a former Microsoft exec.

Whoever gets the job needs to move quickly on a range of actions needed–from deciding the strategy with regard to a search deal with Microsoft (MSFT) to determining whether a long-running merger deal with Time Warner (TWX) online unit AOL should happen.

So far, Yahoo’s board has also gotten a lot more rebuffs from outside execs than expected for the top spot.

This is no surprise, due to the highly difficult task of turning the company around. While rich in assets and online traffic, Yahoo has suffered over the last year from a range of internal and external troubles.

Bartz is certainly an experienced and very well-regarded tech exec, with the talent to turn things around. She served as chairman, president and CEO for 14 years at the San Rafael, Calif.-based company that makes design software.

While there, Bartz presided over huge growth at Autodesk (ADSK), stepping down in April of 2006, and has since served as its executive chairman.

She also put in stints at other big tech companies, including Sun Microsystems (JAVA), Digital Equipment Corporation and 3M (MMM).

More interestingly, Bartz is also on the boards of a blue chip list of companies and organizations, including Intel (INTC), Cisco Systems (CSCO), NetApp (NTAP), and the Foundation for the National Medals of Science and Technology.

Yang is also on the board of Cisco, and Yahoo President Sue Decker is on Intel’s, so Bartz is a well known quantity to Yahoo.

She is also exactly the kind of serious, seasoned public company CEO with tech experience whom Yahoo’s board has told investors and others it is looking for, with skills to pull off mergers and think strategically.

But Bartz also was in charge of a more old-school kind of tech company, and has less experience in the faster-moving Web environment that prevails now.

Although she toughed it out successfully, Bartz underwent difficult times during the Web 1.0 era, in fact, when investors were worried about Autodesk’s prospects in the online era.

Still, Bartz also has less advertising experience, which is Yahoo’s principal business.

Nonetheless, she is well-liked in the tech community and has ties to key companies Yahoo must deal with, including Microsoft.

Whether Bartz herself is interested in taking over a massive overhaul like Yahoo is unclear. I reached out to her for a comment, but have not heard back yet.

According to her resume on Autodesk’s Web site, Bartz holds an honors degree in computer science from the University of Wisconsin.

According to numerous sources inside and outside the company BoomTown has spoken to this week, board Chairman Roy Bostock (pictured here) has been asserting a new CEO will be named by the new year.

Only 28 more shopping days left until management clarity!

Well, maybe not so much.

Why?

Because there’s actually no “official” search committee that has been appointed by Yahoo’s board, sources said.

Instead, an informal group–with Bostock and board member Gary Wilson at the lead, with help from all the rest of the board–is conducting the effort jointly, along with exec search firm Heidrick & Struggles.

It’s almost like a Berkeley collective!

The board, though, has apparently made a list of six–I have no idea why that is the number chosen–clear criteria for the new leader of Yahoo (YHOO).

The first is that the candidate have “extensive” experience as the CEO of a public company. Another calls for media and advertising expertise. And mergers and acquisitions experience. Also strategic skills.

That’s a tall order, of course, to deliver on in such a short time.

In addition, the idea of bringing in at the same time a No. 1 and No. 2 exec has been considered, with one stronger in media and the other in product and technology.

It is hard to find an exec with skills in both, even in the best of situations.

Think pairing someone like News Corp. (NWS) COO Peter Chernin with Google (GOOG) exec Tim Armstrong or DoubleClick exec David Rosenblatt with, say, Yahoo CTO Ari Balogh and you get the concept.

But many who have spoken to board members at Yahoo said they get the distinct impression that they are leaning toward one of their own–former Nextel head John Chapple, former media exec Frank Biondi, Jr. or former Microsoft (MSFT) exec Maggie Wilderotter (pictured here).

That is due to wanting someone who has operational skills, but also can get things moving at Yahoo, while also being able to continue to work with Yang.

He will remain on the board and regain his title of Chief Yahoo. Sources said Bostock and other board members believe that Yang remains an important and beloved figure at Yahoo among the rank and file and needs to remain involved going forward.

Another key reason for wanting to pick an insider is that Bostock has also intimated that Yahoo was ready to do a deal at any time in the next week or so to merge with AOL–with or without a new CEO in place.

Consummating that might irk an outside candidate, who would have to manage the complex merger without input into its making, rather than a board member, who has been involved.

Talks between Yahoo and AOL have been never-ending and due diligence extensive, as this column has previously reported, although slower of late, because of the uncertainty around Yahoo leadership.

And the price–or, more specifically, the percentage–Yahoo has been willing to fork over to AOL owner Time Warner (TWX) has been the key sticking point, especially as Yahoo’s stock has waned in price.

Yahoo has long wanted to give Time Warner about 20 percent of the merged company, while Time Warner has wanted one-third. At current prices, that’s about $3 billion in value versus $5 billion.

But, if such a deal could finally be struck, it might be a dramatic and apt swan song move for Yang (pictured here), which could inject a bit of excitement into the mostly lackluster situation for both Yahoo and AOL.

Yang and others at Yahoo have also long felt that the company would have more leverage with Microsoft if it also controlled AOL–when and if it formally restarts its talks with the software giant about some sort of search deal.

Interestingly, many close to the situation said that there is still resistance among the “old guard” of the Yahoo board to doing a search deal at all.

New board member and activist shareholder Carl Icahn has loudly called for such a partnership with Microsoft.

But there is still extensive internal debate about whether it is wise to decouple search from Yahoo, many sources said, even if it brings in massive guaranteed revenues and allows Yahoo to cut costs in its engineering ranks.

Said one person close to the situation: “A lot of what has been going on is the board trying to figure out what kind of company does Yahoo aspire to be. That determines the type of person they bring in.”

When everyone else has been selling, it seems Carl Icahn has decided to throw good money after bad–as in nearly $1 billion bad–by buying almost seven million more Yahoo shares, according to a regulatory filing.

Why is he doing it? BoomTown is guessing that the billionaire investor thinks he can recoup some of his massive losses in Yahoo, as Jerry Yang prepares to step down, and the board, on which Icahn sits, names a new leader.

That’s why my guess is that the choice of a new CEO is likely to be sooner than later and much more Icahn-friendly.

That could point more clearly to perhaps one of two execs whom Icahn brought with him to the Yahoo (YHOO) board–either former media exec Frank Biondi Jr. or, more likely, former Nextel exec John Chapple.

Another theory is that Yahoo will pick a more low-key, tech-oriented outsider, an operational star who can get things turned around at Yahoo without a lot of fuss, similar to choices made for eBay (EBAY) in its pick of John Donahoe, and Mark Hurd at Hewlett-Packard (HPQ) recently.

One of the names being bandied about in that regard is HP exec Todd Bradley (pictured here).

Bradley is in charge of its massive Personal Systems group, a $28 billion annual business, which includes personal computers, mobile devices, technical workstations, digital televisions, personal storage solutions and Internet services.

Interestingly, another top HP exec, Vyomesh (VJ) Yoshi, who runs its Imaging and Printing group, is currently a director on the Yahoo board.

In any case, the purchase of 6.7 million more Yahoo shares for about $65 million by Icahn over the last several days is definitely a move to watch.

Icahn, who waged a proxy fight against the Internet giant, owns stock that has lost about $900 million in value since he bought about five percent of Yahoo earlier in the year.

That loss comes from his purchase of about 70 million shares in the spring, at about $25 a share, of Yahoo stock, right in the midst of its takeover battle with Microsoft.

Yahoo shares closed Friday at $10.58, up 33 cents.

With the new purchase, Icahn now owns about 5.4 percent of Yahoo, which–combined with three board seats–gives him a lot more clout over decision-making and in forcing the current board to make a CEO pick who will be more interested in doing some sort of deal with Microsoft (MSFT) quickly.

Icahn has long agitated for Yahoo to sell all or part of itself off to the software giant, a move that has been resisted by Yahoo leadership. Instead, Yang tried to pull off a deal with Google (GOOG), which failed.

But that leadership is about to change, as the board searches for a new CEO to replace Yang, who said he was ready to step down a few weeks ago.

Lots of names have been floated for the job–from News Corp. (NWS) COO Peter Chernin to DoubleClick head David Rosenblatt to Google exec Tim Armstrong, as well as former Yahoo COO Dan Rosensweig.

Most sources inside and outside the company do not expect its current president, Sue Decker, who is also up for the job, to be selected.

But many point to a current Yahoo board member as a quick choice, in order to get some key initiatives moving, such as a Microsoft deal or a merger with Time Warner (TWX) online unit, AOL.

That points to someone like Chapple (pictured here), who has been querying a range of midlevel Yahoo execs of late, presumably to get a lay of the land at the company for the board.

He or perhaps even board member Maggie Wilderotter could be picked as an interim CEO, in order to signal to investors that true change is on the way at Yahoo.

Whoever is chosen needs to move quickly said many I spoke to about the Yahoo CEO job.

Wrote one experienced Internet exec in an email to me, reflecting a very common sentiment:

“Whoever comes in is going to have one shot to define the product to the consumer in a way that differentiates it from the rest of the market and provides unique value. Their brand is fuzzy right now. And they’ll have to find a uniqueness in their ad sales so they are not relegated to being the also-ran.”

Well, with all the money riding on it, Carl Icahn certainly has to hope that does not become the case.

And, no surprise, he is the No. 1 choice of most inside and outside Yahoo (YHOO) in the wake of the news late yesterday that current CEO and co-founder Jerry Yang is stepping down.

And why not? Chernin has the right resume: Experienced at running large and complex organizations; savvier than most in media about the Internet; able to make the kinds of dramatic decisions needed; and, perhaps best of all, signaling–via the Los Angeles Times–just this past week that he was open to leaving the powerful media and entertainment conglomerate for something new.

Well, Yahoo would certainly be new for Chernin, in terms of a corporate cleanup challenge, especially compared to figuring out how to make bank on plush toys from “The Simpsons.”

And, while the risks are many, if Chernin (pictured here) managed to turn around Yahoo, he could make a huge fortune too, given Yahoo shares have languished of late, much in the same way they did when former CEO Terry Semel came to Yahoo from Hollywood in 2001.

But it’s not altogether clear whether Chernin would actually leave his powerful perch at News Corp. (NWS) — which owns Dow Jones and owns this Web site. He has been ensconced there for a dozen years, building a huge reputation as a sharp exec (No, Peter, I am not kissing up, as I think Yahoo would wear even you down very, very quickly).

That’s even though many note he is not likely to take over as CEO from its iconic leader, Rupert Murdoch. The media mogul is widely expected to favor one of his own children to lead News Corp. next.

And the 57-year-old Chernin already makes close to $30 million in his current job, which is definitely challenging.

And, although Chernin has been involved in the News Corp.-owned MySpace and has had success backing the Hulu online video site, it is not nearly as hard as the five-year turnaround quagmire (plus no fabulous media mogul perks either) that Yahoo could turn out to be.

In addition, privately to other News Corp. execs, Chernin has regularly pooh-poohed a move to a digital company, even though he is always on the short list for a lot of big Internet jobs — such as the long-unfilled post as digital head at Microsoft (MSFT) more recently.

So, who else to take over from Yang, who will return to his job as Chief Yahoo after stepping down from the company as soon a search for a replacement CEO is successful?

Well, here is BoomTown’s own shortish list, based on asking a wide range of people inside and outside Yahoo, all of whom are important digital players in their own right.

INSIDE YAHOO

Sue Decker:

The current president of Yahoo is certainly being “considered” for the job, which is a polite term for not really being considered at all. While Decker is an intelligent and thoughtful exec, like a politician with a record, she has had her hand on the operating tiller at Yahoo for too long not to get deservedly blamed for its current situation.

In addition, she is radioactive to big investors, who have told the Yahoo board in no uncertain terms that she is a nonstarter.

Maggie Wilderotter:

The former Microsoft exec, who has also been a public company CEO, is an interesting idea floated by some, who think the Yahoo board might turn to one of its own directors, as a short-term solution to stabilize Yahoo.

Wilderotter has been much focused, said several Yahoo execs, on cost-cutting at Yahoo and certainly is not as tarnished, being a more current board member. But she is a largely unknown quantity in the Internet space and, most importantly, at Yahoo.

John Chapple:

The former CEO of Nextel is one of the two board members (former media Frank Biondi Jr. is the other) recently picked by Carl Icahn, when the activist shareholder was admitted on the board as part of the proxy fight settlement.

Chapple has, sources said, been conducting chats with Yahoo execs lately, perhaps as a way to get a lay of the land. If he got the job, it would be clear Icahn had won his Pyrrhic victory (and personal financial defeat) against Yang.

OUTSIDE YAHOO

Dan Rosensweig:

The very funny, but brash, former Yahoo COO is definitely a favorite within Yahoo’s ranks, except for those who don’t like him. But it’s clear Rosensweig does know and love Yahoo, is close to Yang and, ironically, enjoys a tight relationship with Microsoft CEO Steve Ballmer, who also wanted him for the digital head job.

Also, Rosensweig, who does have operating chops, has gotten some much needed time away from Yahoo, as a partner at the tony media investment firm, the Quadrangle Group.

Meg Whitman:

Another dreamy CEO choice, except she has already been a big company CEO at eBay (EBAY), has proved her mettle in building it to a powerhouse–despite the online auction site’s currently harder times–and has the giant fortune to prove it.

And, oh yes, she is likely to be using that pile of cash to run for governor of California, on the Republican ticket.

Jon Miller/Ross Levinsohn:

The Bobbsey Twins of the Internet, the pair are now having a very good time running their own investment company, the Velocity Group.

But, aside from some questioning whether he can make the quick decisions needed at Yahoo, Miller (pictured here on the right), the former head of AOL, does not want to leave his New York home and cannot take any job anyway until his noncompete with Time Warner (TWX) runs out in March.

And former Fox Interactive Media head Levinsohn likes Los Angeles, and probably is too fast a personality for Yahoo (his going there would be a shock to its system, but would be endlessly entertaining to me personally).

Tim Armstrong:

The top ad exec at Google (GOOG) certainly is an interesting idea, although has little of the product experience needed to run Yahoo. But he is a well-respected advertising figure–where Yahoo needs to shine–and could do well with a lot of strong execs under him.

He is also not on a CEO path at Google–paging, Larry Page!–and could be interested in proving he could run a company on his own.

Kevin Johnson:

The former Microsoft exec was supposed to be running Yahoo, if he and Ballmer pulled off their takeover attempt earlier this year. They did not, and Johnson then left Microsoft to run Juniper Networks (JNPR) in Silicon Valley, right up the road from Yahoo, in fact.

But Johnson is likely subject to a noncompete by Microsoft and a strong contract at Juniper too. Still, a very sharp exec, he definitely has the operating, political, technological and digital skills to take on Yahoo. Also, ironically, he and Yang really get along well and like each other, despite the takeover battle.

Of course, there are a lot of other ideas: Disney (DIS) online exec Steve Wadsworth; the outside-the-box choice of former Procter & Gamble (PG) marketing wizard Jim Stengel; Microsoft digital exec Yusuf Mehdi; CBS (CBS) digital head Quincy Smith (whose hyperactive dealmaking would likely lead to a mutant merger between CBS and Yahoo); and former Cisco (CSCO) and current Joost CEO Mike Volpi.

Please post suggestions below or, better yet, send tips to me at here.

Please see this disclosure related to me and Google.

With a $10 stock price, the turning down of Microsoft’s $31 a share offer, a collapsed search advertising deal with Google (GOOG), fleeing execs and bad news aplenty, it’s easy to blame Yahoo CEO Jerry Yang and call for his ouster.

After all, the buck does stop with him.

Or does it? Because, to my mind, if there is anyone to cast stones at in the ongoing crisis at Yahoo, BoomTown would have to toss a large boulder in the direction of the company’s incredibly shrinking board.

The board is, after all, Yang’s boss and the ones charged with keeping Yahoo (YHOO) on track. That’s why their apparent stasis is just astonishing, if it were not quite so appalling.

And that’s also the opinion of major Yahoo investors, who have been watching with horror as their equity in the company has also shrunk to an infinitesimal size, with little apparent movement by the directors of Yahoo.

“They have no sense of urgency or seem to feel any pressure to do anything, even though by every metric they have failed,” said one investor I recently spoke to, who has been in touch with some Yahoo board members recently. “Should they kick Jerry out? Should they restart talks with Microsoft? Should they consider other options to turn the company around? And while they’re telling me they are going to do something, nothing happens.”

Said another big investor: “With all the other things going on in the economy, I have just decided to move on and write Yahoo off…but the lack of action by the board is really hard to understand.”

What’s hard to know is exactly what new board member Carl Icahn–the billionaire shareholder activist (pictured here), who joined after a very public fight with Yahoo, along with two others he hand-picked, former Nextel CEO John Chapple and former Viacom exec Frank Biondi–has been up to.

Not much, it seems, for the typically noisy gadfly, who owns five percent of Yahoo and has lost a fortune doing so.

Last week, Icahn did suddenly pop up on CNBC and make a declaration: “We believe as large shareholders that eventually we at Yahoo should, if available, make a deal with Microsoft to do search. We could save a fortune at Yahoo if Microsoft could do search for us.”

Yang himself made a similar suggestion at the Web 2.0 Summit last week that Yahoo was open to a deal to sell the whole company to Microsoft.

It was an offer Microsoft (MSFT) CEO Steve Ballmer shot down the very next day, although the software giant is still obviously interested in a search deal.

But sources at Microsoft tell me that Ballmer has said recently that he has no idea who to work with at the company to get anything done and that Yahoo–especially its board, since his relations with Yang have not been successful–has to be the one to act first.

That means, of course, that the ball is squarely in the Yahoo board’s court to do something–at this point, really, anything.

And those directors should be hard at work trying to hit it, instead of not even deigning to take a swing.

Apparently, everything but Nextel is on the table.

Or, rather, Nextel is still on the table, but no one’s interested in buying it at the $5 billion+ price Sprint’s asking. Said Chris King, an analyst at Stifel Nicolaus, “I’m not sure they were going to see that kind of valuation, especially in this type of capital markets environment.”

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But Yahoo’s annual meeting on Friday will be more of a humdinger than usual (and BoomTown is all signed up to go and waiting for confirmation, after agreeing to a long fascist list of no-you-can’ts from Yahoo PR).

So many moving parts, including who, who, who will Yahoo (YHOO) and Icahn decide on for the two other board members to join besides Icahn (pictured here)?

Actually, I mostly want to know who gets to sit next to Icahn at the first board meeting. I vote Yahoo CEO Jerry Yang!

But I digress, let’s hazard a guess, shall we, of who the newbies will be?

The Icahn slate includes: Lucian A. Bebchuk, Frank J. Biondi, Jr., John H. Chapple, Mark Cuban, Adam Dell, Keith A. Meister, Edward H. Meyer, and Brian S. Posner, as well as the late addition of former AOL (TWX) head Jon Miller.

Yahoo must consent to Icahn’s choices and don’t actually have to seat the new members until August 15. Sources said it is interviewing all the candidates right now.

Miller is obviously a shoo-in, given that Yang suggested him to Icahn. Icahn harbors hopes of Miller taking over from Yang (he has talked to a lot of folks about that, in fact!), so getting Miller on board is step one.

But Yang will surely deny everyone the exquisite pleasure by picking Cuban (pictured here), the former Broadcast.com honcho who got rich via a Yahoo acquisition in Web 1.0, never looked back and never ever said “Thanks!”

You can guess longtime Icahn cronies Biondi and Meister are unlikely, given that it would be like having Carl times two (although I am not completely ruling out the more media-experienced Biondi).

Meyer certainly has the advertising chops as former chairman and CEO of Grey Global, but he might be considered too old-school for Yahoo.

Investor Adam “Brother of Michael” Dell seems more of a long shot, although he is certainly not objectionable to Yahoo. But if the company is looking for experience in Yahoo’s businesses going forward, Yahoo might not consider Dell the strongest of the group.

Same for mutual fund star Posner. An obvious brainiac, but just knowing how to make money on Wall Street does not really make him an ideal person to be on the board of an Internet company.

Now, Bebchuk is indeed intriguing, given his Harvard law professor/shareholder activist background and his pay-for-performance clarion cry. But Yang and some other current board members, who have recently been dinged by some proxy-advisory services for too much compensation compared with their record, might not like having Bebchuk so close by.

Thus, overall, from good-fit perspective, I like another former exec, John Chapple (pictured here) of Nextel best of all because mobile will be increasingly important to Yahoo in Web 3.0 (frankly, it better be, as Web 2.0 has not been too kind to Yahoo).

Via Sprint (S), Chapple knows from big mergers and he knows how to makes deals. He has been the operator of a digital company, unlike many of the others. And he is also an entrepreneur, which is a plus.

But whoever from the Icahn group gets the nod, one thing is certain: If they’re looking for friends on the old Yahoo board, they might want to get a dog instead.

Not the most attractive of acquisition targets. But beauty is in the eye of the beholder, in this case T-Mobile parent Deutsche Telekom (DT) which is reportedly considering a bid for the wireless outfit, whose worsening losses have left it ripe for a buyout. By swallowing Sprint (S), DT could gain some spectrum in the States and stave off a price war between the mobile carriers, or so the “thinking” goes.

Thing is, an acquisition of Sprint entails an acquisition of Sprint’s problems–and there are many. It would also require DT, which operates a GSM/EDGE network, to manage Sprint’s 3G CDMA network and Nextel’s legacy iDEN system. That’s three different network standards. And then there’s Sprint’s WiMax operation, XHOM, to deal with. That’s the makings of a real Greek tragedy of a business story right there. Said Avian Securities analyst Matthew Thornton, “While the differing network technology standard does not necessarily eliminate the possibility of a deal, it does significantly raise the costs and complexity of the combination.”

Michael Nelson, an analyst at Stanford Group, agreed. “You really cannot underestimate the level of complexity that that entails,” he told Bloomberg. “There is a significant amount of integration risk.”

Not the most attractive of acquisition targets. But beauty is in the eye of the beholder, in this case T-Mobile parent Deutsche Telekom (DT) which is reportedly considering a bid for the wireless outfit, whose worsening losses have left it ripe for a buyout. By swallowing Sprint (S), DT could gain some spectrum in the States and stave off a price war between the mobile carriers, or so the “thinking” goes.

Thing is, an acquisition of Sprint entails an acquisition of Sprint’s problems–and there are many. It would also require DT, which operates a GSM/EDGE network, to manage Sprint’s 3G CDMA network and Nextel’s legacy iDEN system. That’s three different network standards. And then there’s Sprint’s WiMax operation, XHOM, to deal with. That’s the makings of a real Greek tragedy of a business story right there. Said Avian Securities analyst Matthew Thornton, “While the differing network technology standard does not necessarily eliminate the possibility of a deal, it does significantly raise the costs and complexity of the combination.”

Michael Nelson, an analyst at Stanford Group, agreed. “You really cannot underestimate the level of complexity that that entails,” he told Bloomberg. “There is a significant amount of integration risk.”