Ken Kelleher has been the owner and CEO of Landmark Technologies since 1998. The company provides IT support, cloud computing, and cybersecurity to businesses.
By Héloïse Chaudot
What are your main priorities and goals in your role?
My main focus is on steering the business in the right direction — making sure we’re growing in a smart, sustainable way, and that we are on course to achieve our five-year plans. That means keeping a close eye on where technology and industry are heading and ensuring we’re always a few steps ahead, especially when it comes to areas such as artificial intelligence (AI) and automation, cybersecurity, and cloud services.
I’m also very focused on our clients. We are a people business, and I spend a lot of time thinking about how we can add more value, be more proactive, and build long-term partnerships.
Internally, I’m passionate about building a strong team and a great culture. I want our people to feel empowered, supported, and excited about what we’re creating together.
I see part of my role as being a voice for the managed service provider (MSP) sector in Ireland — whether that’s through thought leadership, collaboration, or helping to shape the future of tech services here. I am a firm believer in community, and we are active members of MSP and IT communities here in Ireland, the UK, and the US.
What are your biggest challenges as CEO?
One of the biggest challenges I have as CEO is balancing the long-term vision and planning with the day-to-day realities of running the business. You’re constantly switching between strategic thinking and operational problem-solving — and making sure neither gets neglected.
Another big one is talent. In the tech space, especially in Ireland, attracting and retaining top talent is always competitive. So, I prioritise creating an environment where people want to stay, grow, and do their best work.
Also, the pace of change in our industry is relentless. Whether it’s cybersecurity threats, new technologies such as AI, or shifting client expectations, staying ahead of the curve is a constant challenge. But it’s also what makes the role exciting; every day is a school day.
As a founder, there’s the personal challenge of learning to let go of certain things as the company has grown. Delegating effectively, trusting your leadership team, and evolving your own role — that’s a journey in itself.
How do you keep your team/staff motivated?
For me, motivation starts with clarity and purpose. People want to know that what they’re doing matters, so I make it a priority to communicate our vision clearly and show how each person’s work contributes to the bigger picture.
I also believe in giving people ownership — letting them run with ideas, take initiative, and feel trusted. That kind of autonomy really drives engagement.
Recognition is a big part of our culture, too. We make a point of celebrating wins, both big and small. Over the years, we’ve been fortunate to win several industry awards, and that’s been a fantastic way to recognise the team’s hard work and innovation. It’s not just about the trophy — it’s about showing the team that what they’re doing is being noticed and appreciated beyond our own walls.
Finally, I try to keep things human. We’re all under pressure at times, but I want our workplace to be one where people feel supported, where there’s room for a bit of fun, and where we genuinely look out for each other.
What are the challenges facing the industry going forward?
There are quite a few challenges on the horizon for our industry. One of the biggest is the pace of technological change. New tools, platforms, and threats are emerging all the time, and staying ahead of that curve — while still delivering consistent, high-quality service — is a constant balancing act.
Cybersecurity is another major challenge. Threats are becoming more sophisticated, and clients are rightly expecting more proactive protection. That means MSPs need to invest heavily in security expertise, tools, and processes — and that’s not a one-time effort, it’s ongoing.
I think client expectations are also evolving. Businesses want more than just support — they want strategic partners who can help them to innovate, stay agile, and use technology to drive real outcomes. That’s a challenge, but also a huge opportunity for MSPs who are ready to step up.
What new trends are emerging in your industry?
Without a doubt, AI and automation are quickly changing the landscape, and not just in the IT industry. We have been using automation for a long time, but the pace at which AI is developing and reducing the technology curve to just two or three years means all businesses and organisations need to get a handle on the impact that AI can have.
We have already started integrating AI into our service delivery — from intelligent monitoring and predictive maintenance to automating routine support tasks. It’s helping us deliver faster, more proactive support and freeing up our team to focus on higher-value work.
Are there any major changes you would like to see in your sector?
There are a few changes I would welcome in the sector. Firstly, I think there needs to be more collaboration and standardisation across the MSP space, especially around cybersecurity. Right now, there’s a lot of fragmentation, and I believe all businesses would benefit from a framework similar to Cyber Essentials in the UK. While new and changing industry regulations, such as ISO, DORA, and NIS2, are also important, and we work with our clients to achieve these frameworks, not every business requires these levels of compliance. A framework like Cyber Essentials would raise the bar for everyone.
I also believe that the MSP space should have a governing body. As MSPs, we are deeply embedded in our clients’ operations – we’re not just fixing IT issues, we’re managing core infrastructure and sensitive data. So there needs to be a baseline of accountability and security across the board.
As an employer, are you finding any skill gaps in the market?
We are definitely seeing some skills gaps in the market, particularly in areas like cybersecurity and AI. These are fast-moving fields and, while there’s a lot of interest, there’s not always enough hands-on experience or strategic understanding to meet the demand.
To tackle this, we’ve invested heavily in internal training and development. We run structured programmes that help our team upskill in key areas, whether it’s earning certifications, working on real-world projects, or staying ahead of emerging technologies.
We also partner with external training providers and industry bodies to make sure our people have access to the best resources. It’s not just about filling gaps — it’s about building a culture of continuous learning and making sure our team is always growing alongside the industry. We expect our people to continuously learn and support them to do so.
How did your strategy develop in the context of the banking crisis and economic crisis?
As we are nearing our 27th year in business, we have seen a few ups and downs. Thankfully, due to the nature of our business, we were across many sectors during the economic crisis and, if one client fell back, another would grow. At that time, we were doing everything for everyone, so we made a decision to consolidate and focus on what we are good at – IT support and service. That strategy and focus have stayed with us over the years, and it has been good to us.
How has the COVID-19 crisis affected your business/sector?
COVID showed us all overnight that we could work from anywhere. It also showed many business owners that a lack of investment in technology was holding their businesses back. We have retained a hybrid working model since the pandemic and will continue to do so as long as it continues to make sense for us. This gives us a great advantage when attracting and retaining talent and growing our team beyond Ireland.
How do you define success, and what drives you to succeed?
Happy clients, happy team – it’s really that simple for me, but perhaps not always easy! We do have business goals, and I set my own personal and business goals too, so seeing those being accomplished is great. I also like to see people grow into the next phases of their careers. That is very satisfying.
What’s the best advice you’ve been given in business?
It’s hard to pick just one, as I could do a top 50! I have received some great advice over my career, and in many cases, it is all people-related. Business is about people, relationships, and trust, so without a people-first mindset, you won’t get very far.
What advice would you give to others starting out in business?
Back yourself and take more risks, get investment, and do not be afraid to fail. In the early days, I was probably too cautious at times. But I’ve learned that some of the best growth comes from stepping outside my comfort zone. Failure isn’t the opposite of success — it’s part of the journey.
What have been your highlights in business over the past year?
It’s been a really strong year for us, and there have been a few standout moments. One of the biggest highlights has been the continued growth of our AI initiatives. We’ve successfully integrated AI-driven tools into our service delivery, which has not only improved efficiency but also allowed us to offer more proactive and intelligent support to our clients.
Another major highlight has been the recognition we’ve received — winning the All-Ireland Business Foundation (AIBF) IT Super Team of the Year award was a proud moment for the entire team. It’s a reflection of the hard work, innovation, and commitment that goes into everything we do.
We’ve also expanded our team, bringing in some fantastic new talent and continuing to invest in training and development. Seeing our people grow and take on new challenges is always a personal highlight for me.
What’s next for your company?
One of our main focuses is continuing to scale our AI capabilities — not just internally, but in how we help clients to utilise AI to drive efficiency, security, and innovation in their own businesses.
We are looking at new partnerships and potential market expansion — both in Ireland and beyond – and with that, we are actively looking to acquire other suitable MSPs.
Where do you want your business/brand to be this time next year?
I plan to continue to boost our brand visibility — whether that’s through thought leadership, industry recognition, or simply being the first name that comes to mind when businesses are looking for a trusted IT partner.
Ultimately, it’s about continuing to grow with purpose — staying agile, staying client-focused, and building something that has real impact.
What is the best book you’ve ever read (non-business) and why?
I don’t really get the opportunity to read non-business-related books. The last book that stuck with me was Hannibal by Thomas Harris – I was terrified reading each page!
What is your favourite hobby and why?
I got my private pilot’s licence over 15 years ago, and it’s given me some incredible adventures — from flying over France and the coastlines of Spain to navigating the skies above Florida, California, and even as far as Phuket. There’s nothing quite like the freedom and perspective you get from being in the air — I enjoy the preparation, work, and challenge that’s required each time you take to the air. When I achieve my personal and business goals this year, my incentive and reward will be to take a trip as a passenger in a Spitfire.
What is your mantra for life?
“Stay above the noise, trust your instruments, and keep climbing.”
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