Jack Dorsey took on Twitter’s biggest problems, but leaves plenty of challenges for his successor

After a six-year stint as CEO (again), Jack Dorsey is leaving Twitter in a very different place than when he took it over in 2015. Back then, not everyone was excited about the return of the company’s cofounder. Even though he initially came back temporarily, employees and investors were concerned that dual CEO roles — he was, and still is, the CEO of Square — would keep him from being able to tackle the company’s many problems.

“The general feeling among Twitter employees now is trepidation,” The New York Times wrote in 2015 of Dorsey’s surprise return. “Many are concerned at the prospect of Mr. Dorsey’s interim title becoming permanent, given his divisive and sometimes erratic management style and the fact that he had been dismissed and returned to the company before.”

At the time, the company was often described as being “in turmoil.” Twitter was churning through executives, and investors were concerned about lackluster user growth. Journalists and other pundits often noted that Twitter never knew how to explain what it was or why it mattered. The actual service had barely changed in years. Harassment was rampant, and relatively unchecked.

Much has changed since then. Hand-wringing over Dorsey’s two jobs never really abated, but turnover at the top of the company eventually slowed, and Twitter started growing again. The platform still struggles with harassment, but has made a concerted effort at encouraging “healthy conversations” and has significantly ramped up its policies against hate speech and harassment.

More recently, the company has undertaken a number of ambitious initiatives to change its core features and create new sources of revenue. In the last year alone, Twitter has introduced new features for live audio, groups, and payments. It rolled out creator-focused features like Super Follows, and acquired a newsletter platform for longform content. Last month, it introduced Twitter Blue, a subscription service aimed at power users. The company is also in the early stages of BlueSky, a plan to create a decentralized standard for social media platforms.

But incoming CEO Parag Agrawal will still be inheriting significant challenges alongside all the shiny new projects. Though the company has made strides in increasing conversational “health,” it’s also grappled with where to draw the line between free speech and toxicity, particularly when political figures are involved. And, like other platforms, the company struggled to rein in misinformation during the COVID-19 pandemic and 2020 presidential election.

“Dorsey leaves behind a mixed legacy: a platform that’s useful and potent for quick communication but one that’s been exploited by a range of bad actors, including former President Donald Trump, who did his best on Twitter to undermine democracy—until Dorsey’s people finally had enough and shut him down,” says Paul Barrett, deputy director of the NYU Stern Center for Business and Human Rights, who has researched social media polarization.

That Twitter under Dorsey did eventually permanently ban Trump has only made the company more of a target for politicians. And that’s unlikely to change just because Twitter’s new CEO has been one of the company’s lowest profile executives.

Agrawal is taking over as social media platforms face a bigger reckoning about their role in society. As lawmakers eye regulating algorithms and other reforms, Twitter has started to research algorithmic amplification and potential “unintentional harms” caused by its ranking systems. It will now be up to the company’s former CTO to steer that work while navigating scrutiny from lawmakers.

Agrawal will also inherit ambitious goals Twitter set earlier this year: To double its revenue and grow its user base to 315 million monetizable daily active users (mDAU) by the end of 2023 (the company reported 211 million mDAU in its most recent earnings report). And there are some signs he may be well positioned to make that happen. While Twitter under Dorsey has been slow to make decisions and release updates, Agrawal has been a proponent of new features like Bitcoin tipping. He also over saw Bluesky, the decentralization project.

The company has been betting that moving away from advertising and leaning into subscription services and other new features will help it get there. But Twitter is hardly alone in pursuing creators and subscriptions, and it’s not clear the company will be able to easily persuade large swaths of users to start paying for extra content or premium features.

Twitter’s new CEO seems to be well aware of the challenges ahead. “We recently updated our strategy to hit ambitious goals, and I believe that strategy to be bold and right,” Agrawal wrote in an email to employees he shared on Twitter. “But our critical challenge is how we work to execute against it and deliver results.”