Born and raised in Hamilton, his early years were simple; sun, surf, and sand at the family bach in Whangamata. Those sun-filled days and the thrill of ocean waves have become the foundation of his character. “I loved Advanced PE at school, I spent most of my time on the windsurfer or the golf course!” says Ben. 

Ben’s dad, Peter Gilbert, was the PE teacher at St Paul’s Collegiate School and had been there for more than 25 years by the time Ben walked through the front gates. Ben says, “My decision to attend St Paul's was almost a rite of passage, with Dad having dedicated more than 25 years of his professional life, it was a natural choice.” St Paul’s offered a good mix of academics along with cultural and sporting activities. 

“I was really fortunate to have a number of people on the staff at St Paul’s who gave me opportunities and pushed me to be my best. The teachers I remember most were Paul Wilson who was then housemaster of Hall House, Mike Groom who taught me English and was my football coach, Gary Baillie (for a subject that I was good at), and Neil Muirhead (for a subject that I wasn't). I should also call out my dad, for being the only person to give me a detention - and he gave me three!”  

After St Paul’s, Ben took a gap year, embracing a European adventure under the guise of teaching and sports coaching at Aldenham School near London. As Ben says, “Reality hit when I returned to Hamilton to study law and business at the University of Waikato”. His professional path was typical of a law graduate, marked by internships and followed by four years at a prominent Auckland firm. However, an opportunity with Microsoft, one of the firm’s clients, shifted his career into high gear.

Now, as Microsoft’s legal expert for artificial intelligence across Asia, Ben's role is both complex and fascinating. He navigates the uncharted waters of AI law, advising data scientists, negotiating AI terms, and advocating for responsible technology use. “In 2017, I was working with engineers to develop an ‘old school’ AI legal chatbot to make life easier for Microsoft lawyers and internal clients so I made sure the avatar for the bot was a kiwi.”

The challenge with Ben’s job is that, “Over the past 18 months, the technology and regulatory environment is evolving so often that I almost have to re-learn my job every two to three weeks, that’s exciting but also very challenging.” says Ben. With the rapid evolution of technology and its regulatory landscape, “It’s strange to be a ‘legal expert ’ in something for which there is actually very little law, so much of my work doesn’t have a playbook” says Ben. 

The most rewarding aspect of his work is the opportunity to travel across Asia, interacting with governments, legal departments, and business leaders. Each journey not only offers a glimpse into new cultures but also highlights the groundbreaking ways in which AI is being utilised globally.

As far as what is in store for Ben and his future he says, “So far Microsoft has given me opportunities to work as a lawyer for them in New Zealand, Australia, and Singapore - as well as a stint working on United States matters from the Gold Coast during the Covid-19 pandemic. There are plenty more places to explore, and Microsoft has a business in most of them.”

Ben’s advice to future Collegians at St Paul’s is, “Appreciate how fortunate you are to grow up in New Zealand and have the opportunities that St Paul's offers you. You'll go further and be more fulfilled if you remember this with humility and use it to lift others.”