Driven by a long-held fascination with the scale and complexities of the aviation industry, coupled with a desire to be a “master of chaos”, 36-year-old serial entrepreneur Riccardo ‘Riky’ Vittoria was perhaps destined to create his latest venture.

Acai Travel is a vertical AI-powered B2B SaaS company using Large Language Models (LLMs) to help travel management companies, online travel agents and airlines improve the way they work, saving time and money and improving customer service.

While it’s not alone in this space, Acai specialises in the more complex post booking operations, such as changes, cancellations, disruptions and unused tickets, described by Vittoria as the “nasty side”.

He says its AI back-office agents reduce enquiry handling time by an average of 60% and costs by up to 70%. Meanwhile, its clients’ customer satisfaction scores have risen by as much as 20 percentage points.

Since launching in 2023, Acai Travel has seen impressive growth, with revenues doubling every quarter. Its customers already include tech-savvy TMCs like Perk, World Travel Inc and ALTOUR, plus kiwi.com and Etraveli Group, the parent of European OTAs Gotogate, Mytrip and Supersaver.

“Deploying this technology for TMCs is just a first step, and we are already deploying it to airlines and OTAs,” says Vittoria. “I believe that, eventually, all the supply chain will be interconnected on agentic conversations. So, when something doesn’t work, you don’t have, anymore, a system of APIs with so many point of failures, where in the end experience doesn’t work.

“Instead, you will have intelligent systems, either agentic or hybrid agentic, that will talk with each other, work the databases – even the complex Global Distribution Systems and airline Passenger Service Systems – and proactively solve the case for you. For me, being part of this rebuilding of the foundations of travel is super exciting.”

A Fulbright scholar, Vittoria originally studied mechanical engineering, earning degrees from NYU and Rome’s La Sapienza, and gained research experience in machine learning and airline operations at Singapore’s University of Technology and Design.

His Masters’ thesis was about airline operations optimisation. “I’ve always been passionate about airlines and online distribution,” he says. “Even when I was young, I was always trying to figure out ways that I could hack airline systems and find loopholes and ways to get cheaper fares.”

Before Acai Travel, Vittoria founded 30SecondsToFly, an AI-powered traveller messaging solution and workflow automation for TMCs. Five years later, in 2020, it was acquired by American Express GBT, where Vittoria then stayed for three years to help lead AI innovation.

The arrival of LLMs lured him away from Amex GBT and inspired him to set up Acai Travel. “When I saw the power of this technology, and how it could handle complex situations, I wanted to bring it to everybody,” he said.

“The problem with many travel tech solutions is that they try to solve the problem from the traveller perspective by creating a new booking flow, but that’s actually not the right thing to do,” he said. “We approach it from the back, from the operational side, so doing things closer to the complex GDS operations and mostly in post booking. These are very complex processes that nobody knows unless you have worked on the floor and you have learned it the hard way.”

His time at Amex GBT also taught him the importance of prioritising. “Don’t try to do everything at once. Just try to do narrow automations that are fast to deploy. Often AI transformation programmes fail because they’re not able to deliver an ROI within the year, so the clients’ leadership says ‘This is not working. Why are we investing in this?’.”

Another key requirement, he believes, is that guardrails are in place to ensure there are no errors. “You need to have an accuracy rate that is higher than a human’s by testing it in Copilot first and making sure everything is perfect. Before you deploy it to the customer, it needs to be 99.9% accurate.”

Culturally, Vittoria argues that established TMCs or OTAs are not best placed to develop game-changing tech solutions in-house, so often look outside.

“In order to invent a technology that doesn’t exist, you need that start-up pressure of, ‘Either we figure out a solution, or we die’. You need the best of the best engineers with a fire under their seat. Big innovation doesn’t come from the big establishments,” he says.

Within Acai, Vittoria strives to create a culture that fosters self-awareness, growth and resilience, inspired by cognitive behavioural theories, and Zen and Tibetan Buddhism. He views business as a playground for introspection and transformation, not to make a quick buck.

“I’ve already gone the capitalistic way, creating a company, scaling it and then selling it. This time, for me, it wasn’t enough. I also want to spread a message of enlightenment, empowerment and peace.

“I always start with an approach of trust. I want everybody in my team to not only have a career journey, but have an introspective journey and to learn, by trial and error, how to become a better version of themselves. I want to create companies that inspire happiness and, of course, if people are happier, more forgiving and more united in a company, the business grows faster anyway.”

Quickfire questions:

Are you a good packer?

No, I’m a terrible packer. I always travel with three check-in bags, mainly because I play tennis and have lots of kit to take. My girlfriend gets upset because she travels with a mini backpack and then I’m the one with all the check-in bags!

Aisle seat or window?

I fly a lot with United Airlines. If it’s Polaris I’d go for a window seat, if it’s Economy I’d go for the aisle. I am a little bit claustrophobic.

Film or book? Well, if there is no Wi-Fi, which can be a godsend, I would read a book. But nowadays, on most of my United flights the Internet is pretty good, so I end up working.

Who would you sit next to on a long-haul flight and what would you talk about?

I would like to sit next to a Zen master or the Dalai Lama and I would discuss the workings of the mind.

Biggest achievement?

Career wise, I would say either the sale of 30SecondsToFly to Amex GBT or my Fullbright scholarship. The scholarship took me from Rome, where I was born, to New York, and there I connected with a thousand other students full of passion but all from different cultures and it opens your mind. It was my Auntie who suggested to my father that I should apply for it. A few of us worked as a team and won a start-up competition which gave us funding and access to entrepreneurs who come and teach you about running a company. That was amazing.

Biggest influence and why?

Definitely my Zen teacher Frankie Martinez – also my salsa teacher. And Hector Marcel, my Tibetan Buddhist teacher. They were both very transformative and taught me to smooth my edges and become a more balanced, happier and wiser person. And now I have other teachers, because once you’ve absorbed everything from one, you need to go and find another. Everything is a model, but none of these models are perfect so I try to study different religions or different psychological approaches to find the intersection of all these philosophies, which I think is a bit closer to reality.

What keeps you awake at night?

Sometime the stress of figuring out the right solution or the right business model keeps me awake at night but usually I sleep nine hours, which can be difficult for my girlfriend, who is also a tech entrepreneur, because she only sleeps for four!

Most annoying habit?

Well, I don’t drink alcohol, or coffee, and I don’t do drugs, but my guilty pleasure is eating. My colleagues always tease me that I eat anything that is put in front of me. Luckily, I also play a lot of tennis!

Apart from tennis and salsa, any other hobbies?

Yes, I play the piano and the guitar. I didn’t study music formally. I just taught myself. I would play for 10 minutes each morning, and then maybe half an hour, and I just learned. I’ve played the guitar since I was in high school but always wanted to play the piano, so I started in the pandemic lockdowns. I like to play jazz, just with friends.

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