As Twitter and Square team up, can Jack Dorsey lead them both?

Twitter shares closed Wednesday up 5.3 percent, to $26.94.

A few analysts question how Dorsey will balance his responsibilities between the two companies.

This makes his position permanent after the co-founder stepped in three months ago on an interim basis, Re/code reported.

On Thursday, Wall Street was mulling the implications of Dorsey having to split his time between Twitter and Square. News reports have said Dorsey would continue to serve as CEO of his 6-year-old payment startup Square after becoming CEO of Twitter, and Cakmak expressed reservations. During his time as interim CEO, Dorsey has tried to lay out a vision for the company, declaring in July that the platform “has to be the most powerful microphone in the world” and that using Twitter should “be as easy as looking out your window to see what’s happening”.

On Tuesday, there were reports that Twitter is weighing whether to scrap its 140-character limit on tweets – long considered a sacred cow by purists. Today’s price movement is only the latest bad day in what has been a frightful couple of years for Twitter, and the Dorsey appointment could leave a bad taste in the mouths of many investors for a while.

Reappointing Dorsey would be a complicated resolution to Twitter’s confusing and frustrating job hunt.

If Dorsey is anointed as CEO, it would mark his second reign at the company that he helped start in 2006. Recently, Square also filed for an initial public offering (IPO).

On the upside of two CEO jobs for Dorsey, according to the Nomura analysts: Chief Financial Officer Anthony Noto and Chief Revenue Officer Adam Bain are more likely to remain in their executive posts at Twitter.

Back in June, Mr. Dorsey was ambivalent towards the prospect of retaking his former CEO role, stating to Bloomberg, “It’s really up to the search committee and they’re going to look at internal and external candidates”. The company’s user growth has slowed, which has increased the pressure on the company to bolster its revenue.

Dorsey was always the best man for the job, but the only problem was he is already the CEO of Square, and is not willing to give up on that role.