Jack Dorsey faces twin challenges of Twitter and Square

Cantillon: Man who juggles top roles at social media giant and smartphone payment firm

Square’s payment service enables small businesses to accept card and contactless payments. Photograph: Square UK/PA
Square’s payment service enables small businesses to accept card and contactless payments. Photograph: Square UK/PA

If you want something done, ask a busy person to do it. That could be the defence for Jack Dorsey staying at the helm of both Twitter and Square. Two challenging jobs, two distinct sectors, one guiding light.

Dorsey co-founded Square, the payments firm, in 2009. At its heart is a small device that attaches to smartphones and tablets via the headphone jack and acts as a mini card reader for debit and credit card payments. It has proved a hit with small US retailers to date and earlier this week launched in the UK.

Here, Dorsey is better known as the co-founder of Twitter, the social media platform beloved of media types, although less so it seems by the younger members of the general public.

Dorsey was ousted from his role as Twitter chief executive in 2008, with questions over his leadership style. It clearly hurt and led to some soul-searching. A new, improved Dorsey proved his mettle at Square. In 2015, in a move reminiscent of the career rollercoaster of that Silicon Valley deity Steve Jobs, he returned to the hot seat at Twitter after Dick Costolo resigned, initially as acting chief executive before taking the job permanently.

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Developing Square from scratch clearly made Dorsey a more rounded chief executive. Yet there are growing concerns that tackling both jobs at once is a task too far for even him.

Cutting staff

At Twitter, the pressure is on due to fairly stagnant user growth and issues over the use of bots – automated programmes – on the platform. Twitter has already been cutting staff to reduce expenses, while it fends off the challenge from social media rivals such as Snapchat and Facebook.

Square doesn't have things its own way either. While it has narrowed its losses, it's still waiting for a profit. Swedish rival iZettle has investors that include Intel Capital and American Express, and a reported transaction volume of €3.5 billion in the 12 countries in which it operates.

With global ambitions, Square’s decision to launch in the UK makes perfect sense, given the strength of the fintech sector there. Regardless of Brexit, the UK market is too big to ignore.

Next stop Europe? If so then with Twitter's European operations headquartered in Ireland the natural hub for a European assault by Square would be Dublin.

Earlier this week Dorsey spoke of "potential synergies" between Twitter and Square. It seems a bit of a stretch to imagine any potential merger, but one link might be to make Ireland the European hub for both. Certainly that should be the focus of any IDA or IFSC efforts if they manage to get to present their post-Brexit pitch to Dorsey. As for the man himself, the jury is still out on whether he can double-job with success.