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Here's what Jack Dorsey has been doing in his first 90 days as CEO

Twitter co-founder Jack Dorsey. Photo: Getty/Bill Pugliano

Twitter is banking on Jack Dorsey’s vaunted tech prowess to pull the company out of its slump.

But three months into Dorsey’s new gig as Twitter CEO, he’s mostly been displaying his skill as a salesperson so far.

With Twitter’s stock languishing at its lowest point ever and employees losing faith, the 39-year-old Dorsey has had to do double duty, selling people inside and outside the company on Twitter’s prospects.

Dorsey, who splits his time as CEO of the newly public digital payments company Square, has yet to publicly unveil a major new strategic blueprint, or to enact any sweeping operational changes at Twitter, according to people familiar with the matter.

Instead, the first few months have primarily involved subtler, behind-the-scenes changes aimed at fixing immediate problems and tweaking the product, working to improve morale, and putting the company on firmer footing for a comeback. Twitter declined to comment for this story.

Pep talks

Stopping the brain drain has been one of his top priorities so far.

“When people are pissed off and want to leave, he will sit down with them,” said one person familiar with the matter. “He can be very convincing.”

Indeed, the person mentions several Twitter employees who were on the brink of leaving, but were talked off the ledge after a Dorsey pep talk.

“I don’t think we’re talking about committing to stay another year, but maybe for a little while to see if things improve,” the person said.

Dorsey’s powers of persuasion have not always succeeded, most notably when a trio of star product execs left in July, when Dorsey was still serving as interim CEO. And with so many valued employees considered flight risks, Dorsey risks spending too much time on employee interventions.

“The word on the street is that everybody is vulnerable” to leaving, this person said.

Recruiting new talent is also a challenge. Dorsey scored two high-profile coups by bringing on Googler Omid Kordestani as executive chairman, and rehiring Jessica Verrilli in its corporate development group to oversee consumer M&A. But the top corp dev job has been vacant for months. And the company has struggled to convince other potential recruits to come aboard, sources say.

Outside the company, Dorsey has embarked on a charm offensive, meeting with shareholders and clients to sell the Twitter story, including a spree of meetings with marketers in Las Vegas this month at the Consumer Electronics Show.

A delicate balancing act with Square, but no train wrecks

Dorsey helped create Twitter in 2006 and served as its first CEO before being ousted in 2008. He was called back over the summer to replace Dick Costolo, who left after Twitter’s user growth stalled and investors revolted.

The big wrinkle in the story: Dorsey has another full-time job as CEO of Square, which just went public and is a few blocks away from Twitter’s San Francisco headquarters.

That has made for a somewhat unorthodox first 90 days at the helm of Twitter. Dorsey is working full-time at both companies, using his famously compartmentalized scheduling discipline to make the 15 to 18 hour workdays manageable.

Mornings are spent at Twitter, afternoons at Square; Mondays are for senior management meetings at Square and Twitter, while Wednesdays and Fridays involve 30-minute “check-ins” with various managers, according to a person familiar with the matter.

There have been some bottlenecks, particularly during the Square IPO roadshow in November. Personnel and compensation decisions at Twitter that required Dorsey’s sign off, for instance, were slowed, another source familiar with the matter says. But overall, Dorsey has so far managed to balance both jobs without any major train wrecks.

Dorsey has also started to hold long weekly meetings with top Twitter lieutenants, followed by in-depth reports of the discussions that are disseminated internally — a practice that Dorsey imported from Square.

The transparency has been praised by many and has helped instill a sense of unity and mission across the company. But the practice is also something of a double-edged sword, as it has exposed some of the high-level disagreements among executives about strategy and direction. For employees who are considering leaving Twitter, seeing the lack of alignment at the top can be unsettling and doesn’t help persuade them to stay, the source said.

Small changes so far

TwitterChartBI ScreenshotTwitter’s stock has declined during Dorsey’s reign

Twitter has also maintained a steady drumbeat of product changes since Dorsey took over, including releasing the new Moments feature, which helps organise tweets around live events, and integrating Periscope videos directly into the stream of tweets.

Dorsey has hinted at an even bigger change, suggesting that Twitter could move beyond its trademark 140-character limit, letting people post longer tweets, perhaps even up to 10,000 characters, as Re/code reported earlier.

Is it enough?

Twitter’s fourth-quarter earnings report, slated for February 10, should provide more insight into Dorsey’s plans to revamp the business, and whether these changes have helped the business so far.

As one source noted, incremental changes are necessary, but perhaps not sufficient. What Twitter really needs, the person argued, is someone to concede that Twitter has officially lost the battle against upstarts like Instagram and Snapchat, and to have the courage to try something completely new. That is the kind of vision that many Dorsey fans are really banking on.

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