My Business Life: Ken Kelleher, Landmark Technologies

Ken Kelleher, founder and managing director of Landmark Technologies, shares his life and business lessons.

Landmark Technologies is a leading Irish provider of IT and cybersecurity services. With a career spanning decades and senior roles at global tech giants like IBM and Dell, Ken launched Landmark in 1998 from humble beginnings – starting out at a desk in his daughter’s bedroom.

Under his leadership, Landmark has grown into a trusted technology partner for SMEs across Ireland, with a strong focus on innovation and resilience.

Most recently, the company announced a €1.2m investment in a state-of-the-art Cyber Monitoring Centre, creating five new jobs and reinforcing its commitment to cybersecurity excellence.

A qualified pilot, Ken is deeply knowledgeable about the Irish tech landscape and brings an insightful perspective to conversations about the sector’s evolving challenges – from talent acquisition and retention to the rise of AI and the impact of global geopolitical shifts. His business journey is a testament to entrepreneurial grit and adaptability.

Tell us about your background, what journey did you take to arrive at where you are?

I come from a long line of business owners, and a solid work ethic was instilled in us from a young age.

At the age of 13 or so, I had an after-school job as a delivery boy for a pharmacy which paid £10 a week.  I wasn’t the most attentive student at school; I was more interested in having fun and probably spent more time outside the classroom door than inside it. 

When I left school in 1988, I knew no matter what I was going to do in life, I would need to know ‘computers’. I already had an interest in computers as I was lucky to have a Sinclair ZX81 and, later, the Spectrum, when growing up. After a dismal Leaving Cert and a not so bad repeat, I enrolled on what was then a FÁS course for computerised bookkeeping. From there I worked with Notley Cahill, a software vendor and IBM PC dealer, while I studied at night at the Chartered Institute of Management Accountants. 

Instead of qualifying as a management accountant, my interest in IT had been ignited and I switched to developing my networking and PC skills. I then moved to Dell which was a fantastic place to work – I had a vertical learning curve and spent long days and most weekends working. Around that time, I was considering setting up my own business as I now had a good tech background and experience built up. I knew that I would have to learn how to sell and I moved to working in tech sales, initially with The Trinity Group and then later with Lake Communications – both enjoyable and challenging baptisms of fire. In 1998, I started Landmark.

Why are you doing what you are doing? What need are you meeting? What’s your USP?

We are driven by a passion for helping businesses to thrive through technology. At Landmark, we meet a critical need for reliable, scalable IT solutions that empower SMEs to grow securely and efficiently.

Our USP lies in combining deep technical expertise with a proactive, customer-first approach—delivering not just ultra-secure services, but strategic partnerships that evolve with our clients’ needs.  We are responsible for ensuring that critical data is secure, accessible and recoverable.

How did you fund and start the business and what are your growth plans?

The business was started from the corner of my daughter’s bedroom; I had to compete with toys and dolls to get a bit of desk space to do some work. 

The business is completely self-funded and started with a couple of IT contracting roles which I used as an income while building the client base.

We treat every day like a new opportunity to earn our customers’ trust and business. Our five-year plan sees us growing 20% annually and continuing to build with our existing and new clients.

What are your key skills and qualities that set you apart?

I have always seen myself as a good troubleshooter, whether that’s people, business or figuring out solutions for clients.  I can get to the core of the issue quickly and would like to think I can add value.

What (or whom) has helped you most along the way? Who was your greatest mentor/inspiration?

I have always been involved in business groups and peer groups and the latter in recent years has been very beneficial to me. Being at the front of the business can be a lonely place and having other owners to lean on and learn from is invaluable.

I get my inspiration from many areas and would admire business leaders such as Richard Branson, Robert Herjavec and Marcus Lemonis.  However, I am beginning to admire the younger cohort of Irish businesspeople that are doing so much more in such a short time.

What was the greatest piece of business advice you ever received?

“Sometimes you need to slow down to speed up.” I have applied this to the many challenges I have met over the years.

What circumstances/qualities/events can mark the difference between success or failure in life or business?

I have always said the harder I work, the luckier I seem to get!  Success in business is about being at the right place at the right time, as well as building relationships and resilience – all with a bit of luck thrown into the mix.

What was the most challenging aspect of either starting or growing the business?

Growth is always a challenge; there is a lot of competition out there and clients are well informed as information is at their fingertips. 

Vying for potential clients’ attention through social media is hard and we are constantly looking at how we get our message through to the right people.

How did you navigate your business through the pandemic and what lessons did you learn?

We were already well set up to work from home, so it had little impact on the practical side of the business. A lot of our clients had had some digital transformation previously and were able to pivot without too much impact. 

We have retained a hybrid model since, and this has certainly helped us to attract talent and broaden our workforce. During Covid, we maintained the human connection as much as possible with online socials, and have kept that going with our hybrid model, hosting regular lunches, outings and events.

How has digital transformation been a factor in your scaling journey and do you believe Irish firms are utilising digital technologies sufficiently?

Landmark’s business is digital transformation. The pace at which we have undergone digital transformation over the past five years perhaps even outstrips what we did in the previous 10. We would not be able to deliver the same types of solutions and the quality of services – at the volume that we do – to our clients without these transformations. 

We are used to seeing technology curve jumps every couple of years. Artificial intelligence (AI) will shorten these time scales dramatically, and the world is already well on the AI transformation curve.  AI is an opportunity to do more with the same – it’s not about replacing people, but it’s about giving them the best tools for the job and opening new opportunities for businesses.

Irish firms are not grabbing the AI opportunity as firmly as they should be.  There is cautious interest, and I believe businesses that are not actively investing in these technologies now will soon find themselves outpaced by their competitors.

If you were to do it all over again, what would you do differently?

Nothing. I have made all the mistakes and will continue to do so! I have learned a lot and those lessons you can’t get from any management course or consultant.

Who inspires you in business today?  

The many SME business owners who get up every morning and keep on going.  They are the backbone of our economy for job creation, innovation and resilience.  I would also add our competitors – there are some great managed service providers (MSPs) that are innovating and leading, and I love some good competition.

What advice/guidance do you give new hires and how do you nurture talent in your organisation?

“Find a job you enjoy doing, and you will never have to work a day in your life.” We have plans for our teams to achieve great things, and we are here to train, develop and support them. All we ask is that they turn up on time, be present and do their best.

What business books do you read or would recommend?

I am an exponent of the entrepreneurial operating system (EOS) and books such as Traction, How to be a Great Boss, etc. are constant re-reads. Also, Simon Sinek and Patrick Lencioni are always on my recommend list, along with Sandler Sales Training.

What technologies/tools do you use personally to keep you on track?

I’m a big fan of Microsoft CoPilot and tools such as NotebookLM. I am also using Fyxer.ai which is helpful in reducing the time I need to spend on emails, along with Plaud.ai for notetaking and creating action items from meetings.

What social media platforms do you prefer and why?

I am a TikTok user, and I enjoy the short format – although I know it’s probably not the best for my attention span.  I follow business creators as well as creators on travel and comedy.

What are your thoughts on where technology overall is heading and how it will apply to business generally and your business particularly?

Business is being disrupted by AI which is the next industrial revolution. AI, automation, and robotic process automation (RPA) are already having an impact on businesses and, as we adapt to the changes these technologies are bringing, we are already looking at how we can impact our clients’ businesses with this tech. 

Finally, if you had advice for your 21-year-old self – knowing what you know now – what would it be?

Take more risks.  Believe in yourself – you can do this!

• Bank of Ireland is welcoming new customers every day – funding investments, working capital and expansions across multiple sectors. To learn more, click here

• For support in challenging times, click here

• Listen to the ThinkBusiness Podcast for business insights and inspiration. All episodes are here. You can also listen to the Podcast on:

• Spotify

• SoundCloud

• Apple