By Business & Finance 
Before joining Olive for Education as Director of Schools, Ian Gaughran was a cornerstone of Microsoft Ireland’s Education team, dedicating 13 years to overseeing and advancing the company’s educational initiatives across the region. He chose to join Olive after identifying a clear gap in the market and the need for a more focused, school-first solution that could directly address the day-to-day challenges faced by educators. Seeing Olive’s potential to fill that gap, Ian brought his experience and leadership to help drive meaningful change in how digital learning is delivered.
By Rye Baker
What was your first job?
My first job was working in a hotel when I was a student, working mostly evening and weekend shifts. It was a great way to earn some extra cash during the summer and holidays, and it gave me a real appreciation for the pace, pressure, and teamwork that keeps hospitality running smoothly. I also learnt the skillset of talking to people and having a voice. Looking back, it definitely helped shape my understanding of frontline work and the value of hands-on experience, something that still influences our work at Olive for Education today.
What pushed you to pursue a career in this field?
I’ve always believed digital tools should be accessible, equitable and empowering to everyone. I dedicated 13 years to leading educational initiatives at Microsoft Ireland, which reinforced this belief and inspired my move into leadership at Olive for Education. Having a career with purpose and a clear mission is really important to me, and working to address the gaps in Irish education affords me just that.
What would you regard as your greatest achievement to date?
I think the greatest has been seeing young people’s confidence grow as they’re supported and equipped with the digital tools and knowledge we provide. Working closely with schools over the last decade, I have had the pleasure of seeing young people’s resilience, stress tolerance, creativity, and initiative soar by using our 1:1 devices. One school I’ve had a special relationship with is Stepaside Educate Together in Sandyford. This is a school very close to Microsoft, one we would have supported in Microsoft for many years by virtue of being, essentially, neighbours. Going in there and seeing how genuinely excited the students are to get their device, seeing the ways in which the school utilises the device, and how empowering it is to the young people is an achievement we are all very proud of at Olive.
Career-wise, would you do anything differently?
No, I’m positive that everything I’ve done career-wise and otherwise has led me to where I am today at Olive. Having the experience and expertise from Microsoft has given me a uniquely grounded perspective on digital learning. This technical expertise has allowed me to help design and deliver impactful learning solutions so needed in Irish schools. There was a clear gap in the market for a more focused, school-first solution that could directly address the day-to-day challenges faced by educators. I saw that Olive had the potential to fill that gap and leapt at the opportunity to apply my experience and leadership to help in doing so, which has been hugely fulfilling.
In one sentence, how would you define success?
Success is identifying where change is needed, having the expertise and courage to pursue it, and using your experience to create solutions that make a meaningful difference in people’s lives.
What’s the best piece of advice you’ve ever been given?
Something I learnt from my manager at Microsoft: “Surround yourself with people who are smarter than you.” That advice has stayed with me throughout my career. Building a strong team isn’t about having all the answers yourself; it’s about creating an environment where
great people can do their best work. It’s something we value deeply at Olive for Education, and it’s been a key part of our growth.
How do you motivate yourself and your staff?
I believe motivation comes from purpose and progress. I try to stay focused on the “why” behind what we do – helping schools and students access better learning through technology. When teams understand the impact of their work, it naturally drives engagement. I also think consistency and clarity are key: setting clear goals, celebrating wins (big and small), and making space for people to bring ideas forward. Personally, I stay motivated by surrounding myself with passionate people – their energy is contagious.
How do you handle adversity?
Adversity is part and parcel of life, especially when you’re bringing something new and innovative to the world. It is paramount to regularly return to the bigger picture, breaking down tasks and setbacks into manageable parts, and leaning on the unbelievable team we have at Olive for Education. We are a company that offers forward-looking solutions, and that is also how we operate internally, continually evolving our practices, embracing new ideas, and empowering our team to think and act with purpose.
How do you relax?
For me, switching off usually means getting outside. I love walking in the grounds of Kilkenny Castle – it’s a great way to clear the head and get some perspective. More recently, I’ve taken up Padel, which has been a really enjoyable way to stay active and social. I’ve even joined the Kilkenny Tennis Club’s padel committee, so it’s becoming a bigger part of my routine. It’s a great balance to the pace of work life.
What are your aspirations for the future of the business?
I have a lot of aspirations for the future of Olive for Education, and I have no doubt they will be actualised given the quality of our product and the developers behind it. Yes, we have a platform that meets the needs of today’s Irish schooling system, but we are focused on building for what comes next. What we do is not about keeping pace with the digital age – it’s about leading it. The world is ever-changing, with new technology offering opportunities as well as challenges; we want to be at the forefront of both, preparing and supporting schools in navigating them with confidence. Our offerings must always reflect how students will later live and work outside of the classroom, which inevitably requires constant evolution and agility. I aspire that we meet this reality with success while keeping the quality of our platform consistently excellent into the future.
Read More:
Stephanie Wickham, Founder of ExpatTaxes.ie
