New Web Summit CEO on being ‘the right fit’ for the long term

Taking on the top job at Web Summit was never going to be easy, particularly when the task was issued only a few weeks before the company’s flagship annual event in Lisbon. The jamboree had been caught up in the controversy around cofounder and now former chief executive Paddy Cosgrave’s comments on social media about the Israeli action in Gaza. Big name partners were pulling out; speakers were withdrawing, unwilling to be associated with the row.

Few expected the company to settle on a new chief executive quite so quickly. Just over a week after Cosgrave stepped down, saying his comments had become a distraction, former Wikipedia head and US native Katherine Maher was announced as the company’s new chief executive.

The approach came via a phone call, when Maher was just off a plane after a work trip. She knew about the controversy, and that Cosgrave had resigned.

“Someone who knows Paddy reached out to me and said, ‘Would you be open to taking a call?’” she says. That led to a conversation with Web Summit’s executive team and board.

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“Obviously, it was expedited in the sense that it happened very quickly. I went through the process of speaking with various members of the executive team, having sort of a joint interview with the board,” says Maher. “I know it was a competitive process. I know there were other candidates. And they came back to me and they said, ‘We feel like this is the right fit’.”

She certainly has the experience to steer Web Summit’s fresh start. She headed up Wikipedia for five years, leaving in 2021. Before that, Maher was a member of the US think tank the Council on Foreign Relations and worked for Unicef, the National Democratic Institute, Access Now and the World Bank.

Since then, she has joined Atlantic Council (another US think tank), where she is a non-resident senior fellow on democracy and technology, and serves as part of the foreign affairs policy board for the US department of state. She is also a World Economic Forum young global leader, a security fellow at the Truman National Security Project, and chairwoman of the Signal Foundation, the messaging company that has been viewed as a rival to WhatsApp.

But the speed with which the Web Summit chief executive role was filled has raised a few eyebrows. Did Maher know Cosgrave before the appointment? They have a mutual friend. But Maher is adamant that there is no pre-existing relationship there, saying she met Cosgrave only twice before taking up the role, when she took part in Web Summit 2019 as a speaker. And she says she has only heard from him once since her appointment, to say she had done a good job at the event’s opening night.

I also do not see the business alignment between Web Summit and having an independent media outlet that is affiliated with it, particularly one that is quite focused on Ireland

“I‘m getting a number of questions about what Paddy thinks, what Paddy wants, or what Paddy does. And I understand the interest in it. But I think it’s a question for Paddy,” she says. “I also felt that that line of inquiry is a bit misogynistic because the nature of the tech industry is that there are quite a lot of people who know each other. And oftentimes, the size of a man’s network is seen as an asset. And the size of a woman’s network is seen as ‘Did she network her way into the job’?”

Questions about her predecessor and his continued influence on Web Summit – if any – are inevitable, given that he retains an 81 per cent stake in its parent firm. It has also caused some conflict with the media organisations covering the transition. A “quasi legal” letter was sent to some media outlets by Web Summit, from its general counsel Adam Connon, regarding some of the queries that had been made. The issue was raised at an at-times tense press conference during the Lisbon event – Maher’s first as head of the company – where she described it as a “reminder of obligations”. That caused a bit of debate over freedom of expression, something that Maher emphasised that she supported when she delivered her opening address on the Web Summit stage.

She points to her breadth of experience. “Is it an annoyance on a personal level? I think it’s more about being really definitive that I don’t think anybody taking a position such as myself, as a woman, should be subjected to that line of questioning. And I want to draw sort of a firm line in the sand around that.”

That isn’t the only area where Maher was keen to draw a line. Emphasising that the board was independent of its former chief executive was critical. Maher now sits on the board of the company, along with Damian Kimmelman, who Web Summit also appointed as a non-executive director in recent weeks.

One of the first things the board announced was the ending of its funding for The Ditch website. The Irish news website was due to get €1 million over five years in funding from Web Summit, but it is not clear how much of that money has been paid.

Maher was unaware of the website when she came into the role, she says.

“I’m genuinely a believer that it is the role of the press to ask hard questions. I do also believe that it is incredibly important to informed societies to have investigative journalism. I also do not see the business alignment between Web Summit and having an independent media outlet that is affiliated with it, particularly one that is quite focused on Ireland,” she says. “This to me felt like this was a project of the previous CEO, and with the desire to move the company back towards a focus on what happens in the rooms and on the stages, it just didn’t make sense.”

The first big hurdle has been cleared too – Web Summit Lisbon took place this week. Maher had to hit the ground running, learning as she went. When she took to the stage for the opening night, it was to talk about the right to self-expression, and address the controversy that had led to her predecessor departing.

This year’s event has been different, and not just for the obvious reason. With a number of partners and speakers withdrawing, the focus was less on the big names participating and more on the start-ups. Talking to people on the show floor, attendees were mostly happy with getting visibility for their businesses, especially if it meant that they had been bumped up to a speaking slot on one of the stages.

The success of this event this year in terms of the attendance – we do have more than 300 partners on the floor – means that we’re well positioned for the year ahead

So a silver lining for start-ups this year, but what about the long term? Web Summit may need some partners to return. It is still early days, Maher says.

“They are very welcome back. I think the question that I’ll be asking myself is: what does partnership look like? What is the right balance of larger companies with smaller start-ups? Is that the same in every region?” she says. “What I’m really thinking about is the energy and the dynamism and sort of the almost scrappiness of the attendees, and the start-ups who come to the floor are the thing that makes this event special. And so making sure that that experience is both driven in a way that is great for them and has purpose in the world is probably where my focus will be.”

However, with so many key partners pulling out, there have been questions about the financial impact on Web Summit. Maher says the company is in “good shape”.

“The success of this event this year in terms of the attendance – we do have more than 300 partners on the floor – means that we’re well positioned for the year ahead. And so in terms of a financial hit, I actually think we’re fine, we’re in good shape. And that’s going to allow us to be able to go into next year with thoughtfulness about how we want to proceed and the kind of conversations we have with partners.”

But the event will also have to tread a fine line to remain relevant and attract the big speakers to next year’s Web Summit.

“Making sure that Web Summit is a place that attendees feel is excellent is going to be the thing that determines the relevance. It is what brings speakers to the stages, it’s the thing that brings partners to the floor. It’s the thing that brings investors. So the relevance for me is going to be so much around how do we ensure that the way that we’re programming the event is focused on what’s up and coming,” she says. “If we’re able to do that and do that well and stay fresh. I think that’s what allows for the whole flywheel to keep spinning.”