This week, we speak to Aileen Corrigan, the Chief Digital Officer at telecoms giant, Digicel who was recently recognised by Constellation Research on its 2021 Business Transformation 150 for the stellar work she has done in driving the digital agenda across the Caribbean.

It’s surprising Aileen even has time to sit down and talk to us given her relentless agenda. But perhaps what’s most inspirational about the woman driving Digital Transformation across the Caribbean and Pacific, is the fact her door is always open for a chat.

This hectic schedule, which involves being a mum of two, a wife, a cat mum, President of a Jamaican running club, and a keen runner herself, means Aileen has an innate love of simplicity. And that’s where her love for digital comes to the fore.

“What I love most about the digital world are the ideas that come from something that seems so simple. It’s all about simplicity. That’s the wow factor for me. As humans, we love to complicate. But digital has changed all that.”

Stellar advice from someone so well regarded in the fast-paced world of digital. And advice that probably flies in the face of the preconceived notions a lot of us have about the dreaded ‘D’ word.

The crux of the misconceptions and misplaced fear is the fact that many misunderstand the very concept of Digital Transformation. Yes, it’s based on disruptive technologies. But robot armies taking over the world and automated everything are more products of our overactive imaginations.

Better we use that creativity to help the Digital Transformation pending, or likely already underway, in our own workplaces.

But it’s OK to be afraid, says Aileen, even for someone at her level.

“When people are afraid of change, my advice would be to ask for help. Change it up, challenge yourself, be willing to grow.

“I am agile because I know I need to put myself in places that stretch and challenge me. In order to learn, evolve, I thrive off being in an uncomfortable situation.

“Just always ask. Ask the why, from others and yourself. That’s important. I surround myself with people who fill my knowledge gaps.”

You may be reading this from your phone on the toilet, or scrolling from your sofa during your lunchbreak because you now work from home. But think about it, the very fact you can do either of those things is down to Digital Transformation.

Digital has changed the fact we need to be chained to our desks 9-5, or that we even need to have a desk at all!

And when Aileen started out, none of that seemed like a possibility. After studying Industrial Relations at Magill University, Aileen fed her travel bug and headed off on an adventure which took her to Ireland. And that’s where she ended up working in a mobile phone shop.

The next few years were a perfect mix of luck and opportunity as Aileen progressed from sales and distribution to retail, and then to becoming the marketing manager for a huge transformation as four phone companies merged to become O2 retail in Ireland.

Then came the O2 experience, the fully digital store on Dublin’s iconic Grafton Street. (Remember that??) It was like stepping into a spaceship, almost like an other-worldly shopping experience. But for Aileen, it didn’t seem quite so historical.

“I suppose we didn’t think about digital. To us it was just electronic screens. I thought more in terms of creativity and innovation rather than digital transformation.”

And therein lies the secret. While digital transformation is inherently technical, there would be no technical potential without creativity, innovation, good old-fashioned hard work and, like Aileen’s trajectory shows, confidence in your own ability to lead and innovate.

Because of her achievements in Ireland, Aileen was offered an opportunity to join Digicel and off she went to the South Pacific. And it was only then, in remote Vanuatu, that she realised the true meaning of transformation.

“We actually built the phone network across 62 islands and after that I was flooded with thank you letters from locals because we brought them connectivity.”

One particular letter that stood out was from a midwife who told Aileen they would literally save lives because instead of walking miles to find her, families of women in childbirth could now call her and she could be there quicker to save mother and baby where needed.

Digital transformation in practice – improving processes to make life better. Just don’t get blindsided by the technical stuff, which tends to overwhelm and terrify in equal measure.

As Aileen put it: “People get freaked out by the word transformation but it’s not negative. It can change life for the better.”

Fast forward a few years and Aileen had progressed again, first into digital media and then into the digital product space.

And those of you who have been paying attention will remember her degree was in Industrial Relations, she grew up in an analogue world and yet shock, horror – she was gaining traction in the new digital reality. Giving anyone new-found confidence yet??

But despite her personal success and current position, Aileen understands the fear around the unknown, and mostly the fear of job losses.

“People are afraid that there’s some end destination, but there isn’t. It’s a continuous journey. Of course jobs will change, but jobs always have. People used to manually work the land for example, used to set out the presses for the print press. That all changed.”

As scary and intimidating as it all seems now, there will be a point when we stop talking about this as digital transformation, Aileen argues. And she’s right.

But for now, what does it take to succeed? What’s her secret to success?

“I look for people around me with different skillsets. I’m a leader, I set the path. I bring vision and deflect obstacles so people who are the experts can pioneer.

“I also absorb from everyone I work with in my career and I want my teams to be open to learn. They need to be open to see how people do something differently.”

And there’s another secret to her success story, something women in business can perhaps take a little inspiration from in a world where females sometimes feel forced to hide their femininity for fear it will impede their success.

But not Aileen, who cites her “humanity, motherly nature and sensitivity” as her strong points, revealing: “I’m the crier, everyone knows that about me and I think we downplay our sensitive sides too much in the corporate world when they’re actually not weaknesses. It’s natural. It shows you’re human.”

What’s that got to do with Digital Transformation, I hear you ask? Well, a lot actually as this confidence, emotional intelligence and openness will be key to success in any transformation.

Makes sense, right? But it’s still a scary proposition, particularly in light of all the other unknowns 2020 has dumped on us.

Fortunately, many of us already hold many of the skills and attributes needed to make Digital Transformation in our workplaces a success. We just may not know it.


“Oh people are way more agile than we give them credit for, even than they give themselves credit for.

“Look at Covid. Remote work wouldn’t have been in many of our vocabularies not so long ago, now it’s normal. I think we are our own worst enemy because we tell ourselves we can’t when we can.”

So from someone who has been there, done that, and is living the reality again as Chief Digital Officer at a mammoth company in the midst of its own transformation, what the hell is Digital Transformation anyway?

“It’s just about doing things differently. It’s not about huge changes all at once. It’s the small things that add up and make everything less overwhelming. Instead of one big thing, how about doing 1,000 little things that focus on common pain points? Innovation comes where there’s a need.

“I think the mistake too many make is that they start with one huge leap and people become terrified.”

With all the rapid change we’re experiencing daily as a universe, hopefully one ‘new norm’ will be the celebration of failures and the end of our obsession with perfectionism. Celebrate the f*&k ups you might say!

And embracing mistakes is certainly the only way Digital Transformation can succeed.

“We laugh over the learnings at Digicel. There are a lot of bruises, believe me, especially coming from a telco where there’s not a lot of room to fail. But I’ve learned you will fail, you will pick yourself up, dust yourself off and go again,” Aileen admits.

“And like I said before, embracing the little by little approach in terms of change also means mistakes are little.”

But even with the best technologies and even talent, it truly is down to mindset, as Aileen has learned.

“I’m now digital in a telco world trying to drag everyone forward. When I started this journey I thought it would have been easier. But I have learned.”

Now that you mention it, where does a Digital Transformation actually start. (I’m sure it’s a question many of you reading this are wondering.)

“Point one on the roadmap is to have an incubator start-up away from the business. If you try to do this as part of your day-to-day, it will be a lot more difficult.

“One thing I will say is that I don’t believe in outsourcing a Digital Transformation because no one knows your company like you. You just need rebels and disruptors!

“Transformation also touches every facet of the business, so everyone has to play a part. From a management point of view, it isn’t one isolated workstream.”

Such fantastic insight from someone at the top of their game. But to sum it all up, what should be our main takeaway Aileen?

“People get so nervous now with all the talk of digital and new processes and technology. But look at my own personal journey. We’ve all gone through these changes as the world has developed and become more sophisticated. But are we all digital transformers, or wouldn’t you rather say it’s just the new norm?”

You heard it here first. Believe in yourself, don’t be afraid to make mistakes, ask for help, be open to change, start small, keep it simple and embrace your humanity!

Written by Alana Fearon

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