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Adam Bain Is Soooo Nice, Jack Dorsey's Hamlet Act and Other Things You Need to Know About the Twitter CEO Search

To be or not to be -- the CEO.

I finally think I’m beginning to grok the difficulty that it is to manage Twitter.

Case in point: If you interview a dozen people about what is happening there in its search for a CEO to replace its now departed Dick Costolo, you get approximately 23 versions of what is happening.

And this is from sources who would know, both insiders and outsiders close to the company, all of whom are involved to a greater or lesser extent with the selection process that is being run by Spencer Stuart’s Jim Citrin.

Citrin — according to numerous sources who all do agree on this — turned over an initial list of outside candidates to the board last week that included a mix of the expected media and tech execs. And several people who have seen it think it an unexciting list with no one on it jumping out as a really important get.

“It’s a lot of Google people who will never leave and a handful of the usual suspects,” said one person. “It was underwhelming in terms of choice, especially since the insiders are so much stronger.”

Indeed, most agree that the board of Twitter is likely to pick the next leader of the San Francisco social communications company from the current management, focusing pretty clearly on only two candidates who have been much named in numerous reports.

That would be Adam Bain, Twitter’s sales lead; and Jack Dorsey, its famous co-founder and chairman, its once ousted CEO and — oh, yeah — the CEO and founder of another company called Square. (Did we forget to mention that Square is also preparing to go public?)

So let’s start with Dorsey, the enigmatic heart and often-tortured soul of Twitter since its beginning. He is now its interim CEO and has been deeply and strongly involved in the rollout of a variety of new initiatives and management changes (see the not-very-nice departure of comms head Gabriel Stricker, if you want an example of the Dorsey hammer).

Many people close to him and inside the company have come to the conclusion that Dorsey very much wants the job, despite all the complications, and that he has been trying to figure out a way to make it happen. One source noted that the idea of Twitter acquiring Square was actually suggested a while back, although quickly shot down.

There is no question that Dorsey is the most intriguing and bold choice, a true and colorful visionary in a sea of dullish leaders. That’s why he has a lot of supporters on the board, especially those who think Twitter needs one of its founders at the helm, a favored Silicon Valley tactic for revival (see Steve Jobs, Larry Page, etc, etc.).

But while it’s just one block short of insane to think that anyone can run Twitter and have a second full-time job, Dorsey apparently does not believe this, which is complicating matters. Worse, it’s confusing to Twitter’s already perplexed and frustrated investors.

That’s why Peter Currie, the board member leading the search, had to make a statement that Twitter would not allow a CEO who had another CEO job, an implicit reference to Dorsey’s situation at Square.

And at Square, several sources think that Dorsey will make it clear in the coming month, as it moves closer to an IPO, that he is there to stay. It will be interesting if Dorsey is asked about this conundrum today on Twitter’s earnings call and whether he will explicitly say whether he is a candidate for CEO or not.

“Jack has to fish or cut bait on this, for the good of Square and of Twitter,” said one person close to the situation. “He is so iconic that the more he plays Hamlet, the more the rest of the process gets mucked up.”

It has definitely had an impact on the candidacy of Bain, whose appointment as CEO would not be surprising. He has been running Twitter’s advertising and revenue business for five years, and consistently delivered for the company despite an ongoing executive circus and lackluster user growth. Twitter will be a multi-billion dollar business in 2015; it brought in $28 million in 2010, the year Bain started at the company.

Bain is also beloved company-wide. Employees jokingly refer to him as “Chill Bro AB,” and he’s earned respect and admiration from nearly all levels. In fact, you cannot speak to anyone about Bain who does not begin the conversation with a version of “Bain is suuuuuch a nice guy.” (Good god, I think I even have a minor man crush on him.)

For a company like Twitter, which has had its fair share of executive power struggles, this doesn’t go unnoticed. Then again, Costolo was also a crowd favorite.

One knock on Bain is something he can’t control. Like Costolo before him, Bain is not a company founder, a state that some believe left Costolo handcuffed at times. Founders have a “moral authority” to make dramatic changes or business decisions that non-founders don’t always have. It’s especially true in Twitter’s case, where there are two on the board — Dorsey and Evan Williams — with a lot of stock and voting power between them.

Williams is, in fact, a Bain supporter, said several sources, or at least not a Dorsey fan. Another in his camp is Costolo, who had suggested Bain as his successor, according to numerous sources. Costolo remains on the board, for now at least, so will be part of the voting on a new CEO.

There has been some chatter that Bain was the first choice to do that before Dorsey and turned the offer down, due to worries that he needed it to be clear that Dorsey did not want the job. That seems to be untrue, although so is the talk that Bain does not want the CEO title at all and that he is “just keeping his head down and doing his job,” to paraphrase many close to him.

Being super humble — oh, no, not little old me! — is the nice thing to do, by the way, in this onerous process!

Not in the running internally, said many sources, is CFO Anthony Noto, who has worked closely with Bain. While a very accomplished exec, sources said his lack of advertising and product experience is a big deficit.

One interesting name that popped up in my reporting was board member David Rosenblatt, who once ran online ad giant DoubleClick and was at Google after the acquisition. He’d be a natural choice too, but is very happy running 1stDibs, a high-end design marketplace. So, unlikely.

Sources said that the selection of CEO should take place before the next quarter, if all goes well. One thing that is striking, once again, is that there is no woman CEO candidate inside (like Katie Stanton) or outside the company (YouTube head Susan Wojcicki would make the top of my list) being suggested or seriously considered.

(And Citrin has not called me yet, although I don’t want the job and am just keeping my head down over here at Vox Media. It’s never too late to learn to be nice!)

There is also, as always, the looming possibility of a sale of Twitter to Google, Facebook, SoftBank, Microsoft, Apple, etc. Only Google or SoftBank seem plausible and both have expressed definite acquisition interest at various times.

In that case, there would be no need for a CEO. Presumably, the acquiring company has one. If not …

Additional reporting by Kurt Wagner.

This article originally appeared on

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