One of the first Silicon Valley start-ups to go public in a long while–OpenTable–is expected to come to market this week, with venture firms hoping it will prove a tasty treat for Wall Street.

Whether the $42 million initial public offering of the online restaurant reservation service proves to be a bellwether or not is unclear since its business has–despite strong revenue gains over the last two years–run up operating losses for much of its lifespan of 10 years.

OpenTable’s last three months of results, though, have seen a small profit. It makes money primarily from fees from restaurants it gets for a variety of services.

Revenue for 2007 was $41.1 million and for 2008, $55.8 million.

OpenTable is most definitely a creature of Silicon Valley. Its CEO, Jeff Jordan, is a former top eBay (EBAY) exec, and one of its VC backers is Benchmark Capital, among others. Its venture funding has totaled about $50 million.

Barring any unforeseen circumstances, the San Francisco-based OpenTable is expected to price from $12 to $14 a share and then begin trading on Nasdaq under the ticker stock symbol OPEN later this week.

Proceeds from the sale of three million shares, OpenTable has said in regulatory filings, will net it about $16.1 million, with 48 percent of shares being sold by existing shareholders.

The IPO, underwritten by Merrill Lynch & Co., would value the company at about $280 million, which is about five times its 2008 revenues.

(You can look at OpenTable’s initial public filing in January about the IPO here.)

[UPDATED: H-P exec Todd Bradley has been a public company CEO, which I reflected below correctly.]

With Yahoo board Chairman Roy Bostock reportedly assuring investors and others that the company will have a CEO in place by the end of the year, it seems prudent for BoomTown to initiate an official Yahoo CEO Countdown.

After all, this column had a 100-Day No-Sacred-Cows Vision Quest to mark the time that Jerry Yang said he needed to give Yahoo a top-to-bottom look-see when he took over last summer as CEO.

Yang announced he was stepping down on Nov. 17, prompting the search for someone to lead Yahoo (YHOO) to the promised land where BoomTown countdowns are illegal.

But that’s not today, so here’s the 26-days-to-go update:

It looks like Yahoo has almost no chance to nab a top candidate, News Corp. (NWS) COO Peter Chernin. While Yang made nice and Bostock quickly lobbed in a call to get the well-known exec to come in and talk, several sources said Chernin declined even that.

Of course, moguls like Chernin are pros at not interviewing–one media player schooled me that you apparently never show interest in a job and only take it if a full offer is made, because if you don’t get it after chit-chatting, you look like a loser.

But I don’t think it is a slick feint on his part, even though Chernin is now engaged in contract renewal negotiations at News Corp. (which owns this Web site).

Consider: If you were Chernin, would you want to trade your powerful, well-paid, glamorous job in Hollywood and New York for what will surely be a slog of a job in Sunnyvale, and in a cubicle?

And Chernin has told many he is not interested in doing the job, although News Corp. would still love to do some sort of deal to combine its online assets, like MySpace, with Yahoo’s, as it almost did many times.

While Chernin did just take delivery on a Tesla, showing some clear geekiness, and he would be an exciting get for Yahoo, it’s the longest of shots.

The same is true for some other names that have been floated (by me!).

But several of the people are on the Yahoo board’s list too. And while things can change, it is more unlikely any of them will be the pick.

That includes former Yahoo COO Dan Rosensweig, who has a good life now as a media investor; former eBay exec and OpenTable CEO Jeff Jordan, who told his investors he does not want to be in the running and was sticking with the start-up’s IPO plans–if and when the economy recovers (although Yahoo could buy OpenTable and, thus, Jordan); former eBay (EBAY) CEO Meg Whitman, who could be running for governor of California; and former AOL CEO Jon Miller, who is not secretly buying Yahoo, but who could not be its leader anyway, since he is bound by a Time Warner (TWX) noncompete agreement until the end of March.

Another sticking point: The Yahoo board has limited the pool by a list of six criteria that it has drawn up, with the No. 1 being a CEO candidate has to have public company CEO experience.

If enforced, that nixes some folks, like Google (GOOG) exec Tim Armstrong. In addition, Yahoo President Sue Decker getting the nod is even more unlikely, for that and other reasons, according to many.

From my lists, that leaves DoubleClick head David Rosenblatt (his company is now owned by Google); Demand Media’s Richard Rosenblatt; former Viacom (VIA) head Tom Freston; former CNET CEO Shelby Bonnie; Hewlett-Packard (HPQ) exec Todd Bradley; and Juniper Networks (JNPR) CEO Kevin Johnson, who was the Microsoft exec who was key in the Yahoo takeover attempt there.

All have reasons not to either want or be able to take the Yahoo CEO job, so that means there could be a dark horse candidate. (I am now drawing up yet another list of qualified public CEO tech and media execs).

Here’s one: Yesterday, after it was announced he was stepping down from Microsoft (MSFT) in the wake of its hire of former Yahoo tech star Qi Lu as its online leader, I noted that I liked Brian McAndrews for the job.

Plus, the former CEO of aQuantive, which Microsoft bought for $6 billion last year, would be a delicious irony. But those who have talked to him told me McAndrews–who did want the digital head job at Microsoft and was left hanging by the software giant’s CEO Steve Ballmer–seems intent on taking time off now.

Alternatively, one of the two Yahoo board members, Maggie Wilderotter or John Chapple, both have the public company CEO checked off.

Personally, I am betting on one of them as CEO, although I believe it would be better if Yahoo picked a fresh outside choice.

So do a lot of execs remaining at Yahoo, most of whom visibly roll their eyes at the idea of a board member taking over, considering the record of the directors so far in guiding Yahoo’s fortunes.

That’s why the board–which definitely has not distinguished itself by any criteria so far in Yahoo’s long fall from grace–should try to get it right this time, as Yahoo can’t take any more of the way it has been running the show so far.

BoomTown might have been remiss in my post yesterday on top candidates for the Yahoo CEO job, after the news Monday that Jerry Yang is stepping down, by leaving out several key possibilities.

Yesterday’s roster included News Corp.’s Peter Chernin, Google’s Tim Armstrong, Kevin Johnson of Juniper Networks (JNPR) and also two Yahoo board members, among others. (The main internal candidate, Yahoo President Sue Decker, seems unlikely to get the nod.)

So here is an addendum to my initial list–all of whom are Yahoo (YHOO) outsiders.

Tom Freston:

Chernin is not the only media mogul whose name is being bandied about–the other prominent one is former Viacom head Tom Freston.

Freston apparently got shafted by the–let’s be polite here–disturbingly volatile founder of Viacom (VIA), Sumner Redstone, for not buying MySpace. In fact, News Corp. (NWS), which also owns this Web site, did. But Freston remains a well-respected and creative exec and has been dabbling in the Internet space since leaving Viacom.

Also, Oprah and Arianna love Freston–which is all I need to know.

Jeff Jordan:

Jeff Jordan, the former top eBay (EBAY) exec who is now the CEO of OpenTable, was also on the short list for COO at Facebook, a job that went to former Google exec Sheryl Sandberg.

While the restaurant reservations Web start-up has been headed for a public offering, that event has obviously been pushed out indefinitely by the econalypse, which might be just the impetus to convince Jordan that bussing tables all day is too dull.

Some speculate that Yahoo could buy OpenTable and get Jordan in the process.

Richard Rosenblatt:

Another interesting idea is Richard Rosenblatt of Demand Media, a company that Yahoo was sniffing around not too long ago.

The network of social-networking sites and apps maker is an innovative play in the space and might give Yahoo some much needed Web 2.0 DNA. Demand could still be bought by Yahoo, in order to put Rosenblatt into place.

(Rosenblatt, for those who do not remember, ran the company that owned MySpace, and he was key to selling it to News Corp.)

Also, Lance Armstrong likes Rosenblatt.

Shelby Bonnie:

A reader actually made the excellent suggestion of former CNET head Shelby Bonnie, who is now investing in start-ups. Bonnie is another steady exec–despite leaving CNET, now owned by CBS (CBS), under an options backdating controversy–and is well-liked in the Internet industry.

Yahoo would be a much bigger job than he has ever held, although he certainly has both tech and advertising experience online.

David Rosenblatt:

Lastly, especially if Yahoo is interested in an exec who has turnaround talent, there is probably no better a choice than DoubleClick CEO David Rosenblatt. An experienced online advertising exec, he is also sharply outspoken and knows how to get companies in line and fast.

He is also impossibly rich after Google (GOOG) bought DoubleClick out from under–wait for it–Yahoo recently. While he is still running the show for Google, after having decided to stay, Yahoo might present an interesting challenge for the very savvy Rosenblatt.

Please see this disclosure related to me and Google.

It could happen.

That specific scenario of putting someone like the two former Internet execs (they ran Fox Interactive Media and AOL, respectively) in charge of the troubled Web giant is one of the many being bandied about, as Yahoo shares tumble and the company heads toward a potentially ugly annual meeting everyone involved desperately wants to avoid.

In fact, Yahoo’s board and major investors are talking today about various options for the company, including Yahoo’s receptivity to a sweetened deal with Microsoft and also other ways to pull the asset-rich company out of its stock doldrums.

It is not likely to be a very chummy meeting, of course, considering Yahoo’s stock (see this depressing chart to the right) has been drifting inexorably downward with nary a lifesaver in sight.

Yahoo shares sunk ever closer to $20 (it closed today at $20.66, down more than three percent)–a worrisome crossing of the digital Rubicon for the company, given that it makes Yahoo more vulnerable to all sorts of Wall Street machinations.

Besides allowing other large companies like News Corp. (NWS) and Comcast (CMCSA) to consider bids for Yahoo–both have been watching the situation very carefully, sources said–it also opens Yahoo up to attacks from more rapacious private equity investors.

And there is a lot of machinating already, of course, as I have found poking around, with more to come.

Like what?

Like Yahoo back in discussions with AOL once again. Sources close to the situation said that the idea of hooking the pair up have been revived, as Yahoo looks to strengthen itself and Time Warner (TWX) searches for any way to spin off a division it has never been able to juice up.

Of course, Microsoft has also been sniffing around the property too–and almost bought AOL several years ago–and would be unlikely to sit still and let Yahoo grab AOL’s most attractive asset, its Platform A online advertising unit.

(Memo to Time Warner CEO Jeff Bewkes: You’re known as a smooth deal-maker, so paste on that million-dollar smile and get dealing!)

And, more interestingly, are the moves to try to find another CEO and top leadership to come in and run the company instead of Yahoo CEO Jerry Yang and President Sue Decker.

(I had previously posted on possible picks for that job here.)

That could come in either a friendly or non-friendly approach, according to several people close to the situation.

Under the friendly scenario, Yang would voluntarily step aside–and even be upped to non-executive chairman status–while a new CEO and team would be put in place.

A less dulcet approach, which would require an aggressive move by Yahoo’s board–who make head-in-the-sand ostriches seem active–against Yang directly is less likely.

Still, many investors, increasing numbers of employees and even some Yahoo board members have lost confidence in Yang and Decker, who have been trying to set a new course for the company.

But does a new course require new leaders?

Levinsohn and Miller (pictured here, left to right), who now run an online-focused investment fund called Velocity Interactive, are two high-profile former Web execs mentioned most frequently by major Yahoo investors as candidates for that idea.

Sources said could either come in as board members or actually run the company for a time period, while searching for a new CEO, like OpenTable’s Jeff Jordan, Google’s Tim Armstrong or even Microsoft’s Kevin Johnson.

Such as plan could include additional investments by new investors and critical buy-in by current investors–including billionaire activist Carl Icahn, who is waging a proxy fight against Yahoo that is set to come to a head at the Aug. 1 annual meeting.

Most important would likely be cooperation from Microsoft too, which could offer to also buy some of Yahoo and also sweeten its search-ad deal.

It would also require a new plan for Yahoo, which will likely include job cuts and a more drastic refocusing of its business that perhaps only outsiders can do.

As its founder, not surprisingly, Yang has been slow to make the kinds of deep changes many think Yahoo requires to reinvent itself, and Decker has been part of the team that has gotten the company mired in its current state.

While this all sounds incredibly complex, all scenarios point in one inevitable direction: Massive change is coming to Yahoo in the next 30 days, one way or another.

Sources with knowledge of the situation said the company is looking at naming a well-known tech executive to top management, as perhaps even a second-in-charge to Facebook CEO and Founder Mark Zuckerberg (pictured here), to give him more experienced support.

The effort is actually being pushed by Zuckerberg himself.

Those who have heard about the search say Facebook has a short list that includes prominent tech executives, including both men and women (which would be a needed change, since the top six execs at Facebook are currently all men, as you can see here on Facebook’s management page).

BoomTown has some headhunting suggestions of our own, which you can see here. But this is actually not such a new idea at Facebook.

Early last year, for example, Zuckerberg took a long look at former eBay exec Jeff Jordan, who was a contender for the top job there and who is now CEO of IPO-bound OpenTable, as a possible leadership partner.

While that right-hand-man job had been Van Natta’s role in the early days of Facebook, since then Zuckerberg changed his title from COO to Chief Revenue Officer.

In the recent set-up, Van Natta has joined a pool of other executives, none of whom seems to rise above the other.

The current key roster includes Vice President of Product Marketing and Operations Chamath Palihapitiya, a former AOL exec; longtime exec Matt Cohler, whose new title will be vice president of product management; CFO Gideon Yu (a former Yahoo and YouTube exec); Co-Founder and Vice President of Product Engineering Dustin Moskovitz; Jonathan Heiliger, VP of Technical Operations; and CTO Adam D’Angelo.

But some investors and company employees have suggested that this collective, with all major decisions being made by Zuckerberg, needs more structure that a single No. 2 exec might bring.

“I would call it hiring an Un-Zuckerberg,” said one source, a phrase that BoomTown is going to immediately slap on a T-shirt and sell on the site.

Translation: While it is clear that the 23-year-old is a true visionary and a product genius, he still lacks the experience in marketing, advertising, operations and general corporate leadership that will be needed if Facebook goes public in two years’ time.

But, said many sources close to the company, Zuckerberg is intent on remaining CEO of the start-up, which has had a series of ups (hypergrowth; the $240 million investment from Microsoft [MSFT] that valued Facebook at an eye-popping $15 billion) and downs (the Beacon advertising debacle; the $240 million investment Microsoft that valued Facebook at an insane $15 billion).

Zuckerberg flatly said that in a phone interview I did with him earlier this week about the Van Natta departure.

“Yes,” was his full answer when I asked him about whether he would remain in the top slot at the company. Pretty please, any more to add? “No.”

(Of course, that answer was not nearly as good as when Zuckerberg stopped “60 Minutes” correspondent Lesley Stahl in her tracks, after she asked in her recent piece about Facebook about him replacing the two founders of Google as Silicon Valley’s golden geek and he paused for a television eternity and flustering Stahl, before saying with zero affect: “Is that a question?” I still cannot decide if it was a moment of pure genius or absolute goofiness.)

In the interview with BoomTown, Zuckerberg also obliquely referred to more management changes, noting the Van Natta departure was just the beginning.

Last week, that included adding two key Van Natta hires–biz dev head Dan Rose and ad sales head Mike Murphy–to the core executive team.

But neither of them makes for a more dramatic move that some expect.

“It has to be someone who does not overshadow Mark,” said one person who is familiar with the company. “But also someone who can challenge him when he needs challenging. And everyone needs challenging.”

Just like the Cola/Uncola paradigm, in fact, which is BoomTown’s personal and business philosophy.

And who better to give you a primer on that wisdom than the most excellent Geoffrey Holder in this classic television commercial:

Please see this disclosure related to me and Google.

So here is our list of ideas, which include a number of women execs, since a list that Facebook has made apparently includes a few women too.

(And we applaud that, especially since, as you can see from this page at the social-networking site, there are none in its current top management.)

But you do have to begin with the menfolk, since the top choice of mine is one.

That would be someone that Facebook has already looked at, former eBay exec Jeff Jordan (pictured here). Jordan and Zuckerberg talked a lot last year, before Jordan headed off to lead OpenTable, the restaurant reservations service.

It would be hard to entice Jordan, a one-time contender for the top spot at eBay (EBAY), to leave OpenTable, given it is IPO-bound in the next year.

But he has the chops operationally, having led eBay’s North American unit and also its PayPal division. In other words, this man can scale.

But so can former Yahoo (YHOO) COO Dan Rosensweig (pictured here), who left the troubled Internet portal in late 2006, just before it started its long and painful descent into Microsoft’s bear-hug bid.

Rosensweig is now a principal and its-man-in-Silicon-Valley for the tony New York investment firm, the Quadrangle Group, so it is unlikely he would move over to Facebook.

More to the point, it also unclear how well his gregarious nature would mesh with Zuckerberg’s less social manner (although we would pay big bucks to see those two interacting on a daily basis). But Rosensweig, for all his joshing, has the leadership skills and deep contacts in the tech community.

And since Zuckerberg feels so comfy with Microsoft (MSFT), why not its savvy Chief Media Officer Joanne Bradford (pictured here). There, she “leads global product and platform development, content and programming, business development, product management, marketing and branded entertainment for MSN.”

Plus, she might not relish the idea of helping overhaul Yahoo, if that deal is struck, and has the ad sales and content experience too. Also, she is tough, but nice about it.

So is a sharp Facebook social-networking competitor, Bebo’s President Joanna Shields (pictured here). Based in London, she has worked at both Google (GOOG) and RealNetworks (RNWK) and has an international exposure Facebook needs.

Plus, she knows how to work with founders (in Bebo’s case, Michael and Xochi Birch) and has a charming, though squarely in-charge, demeanor.

Google, of course, has been a good headhunting ground for Facebook and the search giant has been fending off poaching off its execs by Facebook regularly.

But why not go for the big game, as there is a long list of prospects in the higher managment echelons of Google.

That includes: Tim Armstrong, president, Advertising and Commerce, North America; Marissa Mayer, vice president, Search Products & User Experience; Susan Wojcicki, vice president, Product Management; Sukhinder Singh Cassidy, president, Asia Pacific and Latin America Operations; David Fischer, vice president, Online Sales & Operations; Omid Kordestani, senior vice president, Global Sales & Business Development; Salar Kamangar, vice president, Product Management.

But we’re partial to a pair of hard-charging execs who lead critical nuts-and-bolts operations at Google: Sheryl Sandberg, vice president, Global Online Sales & Operations; and Shona Brown, senior vice president, Business Operations.

Sandberg (pictured here) is responsible for online sales of Google’s ad and publishing products, bringing experience Facebook sorely needs. She is also politically savvy, having been the chief of staff at the Treasury Department in the Clinton administration.

Former McKinsey consultant and author Shona Brown (pictured here) has been running Google’s business operations since 2003 and knows how to push around, oops, work with two headstrong founders at once. Thus, Zuckerberg would be a breeze for the sharply honed Brown.

But let’s not leave out Yahoo. We have but one choice here (and someone who has reportedly been on Facebook’s list too): Hilary Schneider, its EVP, Global Partner Solutions. In other words, the revenue person.

The former Knight-Ridder exec (pictured here) is well liked at Yahoo and is also steeped in the world of media, which is important to Facebook. While probably a keeper for Microsoft, it might not be her first choice to stay after a forced merger.

There are a lot of other choices–in fact, I am completely leaving out the many media execs who might be good, as well as some longtime Silicon Valley entrepreneurs who would get along a lot better with Zuckerberg.

Off the top of my head: former AOL head Jon Miller; former Yahoo execs Ellen Siminoff and Jeff Mallett; CBS dynamo Quincy Smith; former When and Ofoto entrepreneur James Joaquin; Fox Interactive Media’s Peter Levinsohn; and many more.

But why not go for the man who was Zuckerberg before Zuckerberg was cool. Yes, the shiniest of Golden Geeks himself, Marc Andreessen (pictured here on the iconic Time magazine cover in 1996).

I could go on and on about the similarities I find between the two, if you compared today’s Zuckerberg with the Netscape founder in the mid-1990s.

From their arrogant innocence to their visionary qualities to their enfant-terrible charm, it is almost as if they were separated at birth.

But now Andreessen is all grown up and much, much matured from when I covered him. He has become all calm and sage and he even does a very decent blog.

Plus, he has also started and run a number of start-ups after Netscape, giving him deeper managerial experience over the last dozen years.

And, best of all, Andreessen knows the pressure of being the best-thing-since-sliced-bread in the tech sector, and its inevitable downside too.

Overall, a real mentor and partner for Zuckerberg, making a perfect pair of Golden Geeks.

Please see this disclosure related to me and Google.