Hamish Roy

Class of 1991

November 2025

Our “Alumnus in the Spotlight” this month is Hamish Roy and was written by Aimee Phillips (now an alumni herself, Class of 2025 and English Prefect). From hospitality and tourism to cloud computing and small business ownership, Hamish’s career has been anything but conventional. After 25 years in IT – including 11 years leading his own company, V-Bridge – he is now semi-retired and serving as a Trustee on the Cashmere High School Foundation Board. 

Tell us about what you’re currently doing.

I’m currently semi-retired, but I worked in IT for 25 years. For 11 of those years I was a business owner of a cloud computing company called V-Bridge. V-Bridge provided technological solutions for companies so they could operate effectively. It was a small business, but it gained recognition both in New Zealand and internationally, which I’m really proud of.

When you left school, was this the path you expected to be on?

Not at all. I left school without a clear plan. I went on to complete a hospitality and tourism course at Ara, which I loved. I worked in hospitality for about five years before heading overseas on my OE. While in London, I worked at Royal Mail during the Y2K era – when there was huge concern about computer systems failing as the world transitioned from 1999 to 2000. It was an insane period of my working life.

That experience unexpectedly pushed me toward the tech world, and that’s where my career eventually developed.

What have been some of the highlights of your career, and some of the main challenges?

The highlight was definitely building V-Bridge. Seeing it recognised nationally and globally was hugely satisfying.

The challenges of running a small business with a limited budget were tough, but that’s also where I found enjoyment. I like problem-solving.

The 2011 Christchurch earthquakes were another major challenge for both me and the business. It required a lot of resilience and creative thinking, but in hindsight, working through that period was also a valuable experience.

Who or what has influenced you? Was there anyone at Cashmere who left a lasting impression?

I don’t really have influences outside of my time at Cashmere that shaped my direction. What I valued most were teachers who saw me as an individual.

I really enjoyed Ms Yogi – she was fantastic and understood me. She showed me that humour and fun could be part of learning. Her teaching helped open my attitude a lot.

When teachers took the time to understand my personality, it made learning far more enjoyable.

What do you look back on as highlights of your time at CHS?

My time at Cashmere didn’t shape a specific career path, but it did help me develop an open attitude. I learnt not to put myself into a narrow silo.

Cashmere helped me build the confidence to say “yes” to opportunities – even things I hadn’t done before. That willingness to try something different has probably been one of the most valuable lessons I’ve carried into adult life.

How have you felt about serving as a Trustee on the Cashmere High School Foundation Board?

I’ve thoughtfully enjoyed my time on the Board. I love how the Foundation is connected with a huge community of alumni who support the school both financially and by giving their time. These amazing donations help build a connected community and greatly support all aspects of school life.

Connecting with past students is a great aspect of the role. It’s meaningful to give back to a place that played a part in shaping your outlook – even if you didn’t realise it at the time.