Paddy Cosgrave is synonymous with Web Summit and his resignation is unlikely to be the end of the controversy surrounding this year's event.
Mr Cosgrave resigned his position on Saturday following backlash of his criticism of Israel.
The controversy began when he accused Israel of war crimes in a series of tweets on the violence in the Middle East.
He posted that he was "shocked at the rhetoric and actions of so many Western leaders and governments" supporting Israel amid its conflict with Hamas.
These comments led to a slew of withdrawals from next month's event including actress Gillian Anderson and big names like Meta, Google, Intel and Stripe.
Jess told Newstalk Breakfast that many of the large companies that pulled out are major sponsors of the event.
"He did apologise, but it also came after some pretty big and significant players backed out," she said.
"He made his comments on Twitter; he's been making comments - and controversial comments - on Twitter for a significant period of time.
"What happened over the last number of days is some very high-profile speakers backed out, and then very big important influential tech partners walked away.
"The thing to note is that it's not just that they're putting speakers forward.
"I've been to the Web Summit a huge number of times over the years, and there are entire halls the size of the RDS that have displays that are sponsored by the likes of Amazon's AWS.
"It's not just about presence, it all comes down to the bottom line."
'They're not going to close the doors'
Jess said Mr Cosgrave is more than just a CEO of the Web Summit.
"Organisers are saying, as of this morning anyway, that the event is still going ahead," she said.
"I don't think this controversy has gone away just yet.
"One of the key issues is that for so many years, dating way back to when Web Summit was here in Dublin, Paddy Cosgrave is synonymous with Web Summit.
"What Paddy Cosgrave reportedly told staff on Friday is they've enough cash in the bank, they're not going to close the doors in the morning.
"I do think it's a case of trying to repair the reputation of Web Summit, if that is possible, but every year that I've been at Web Summit in Lisbon, Paddy Cosgrave emcees the main stage.
"He goes on, on opening night, for the first few minutes and offers a State of the Union-style address.
"So, Web Summit - although it has been an incredible network for SMEs, start-ups, for the tech community as a whole - a huge part of it has been around Paddy Cosgrave," she added.
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