Conversations with Leaders: Cathriona Hallahan, former MD of Microsoft Ireland

7 Sep 2022

Cathriona Hallahan (right) in conversation with Ann O’Dea. Image: Connor McKennna/Silicon Republic

After 35 years with Microsoft Ireland, including seven as country manager, Cathriona Hallahan sat down with Silicon Republic’s Ann O’Dea to look back at her remarkable career journey, and to chat leadership styles and lessons.

Having recently stepped down as country manager of Microsoft Ireland, I was all the more fascinated to sit down with Cathriona Hallahan to chat leadership – to both look back at her 35 years at the company, but also to hear more about what is next for this icon of the tech industry in Ireland.

She may have left Microsoft behind, but it is clear that Hallahan was by no means ready for early retirement. When she had time to slow down and have a good think about how the future might look, a clear path emerged.

“I thought, could I take all that leadership experience that I got in a multinational for 35 years in an amazing industry, and bring that to Irish indigenous business and help other businesses grow, and create a portfolio career in different industries, as well as being able to get a better work-life balance,” she said. A new polytunnel has gone some way to achieving the latter, she remarked.

On the business side, Hallahan is currently committed to five board roles. It was clear when we sat down to chat at The Wilde, one of Iconic Offices’ buildings, that this is not an exercise in racking up a titles.

She has been involved in Keelings Fruit from well before she left Microsoft. A family-run business, currently led by Caroline Keeling, Keelings is focused on going global, with a presence already in the UK, France and South America.

“They’re going through that big transformation now of how they move from being an indigenous Irish business to a global business, and the cultural transformation that goes with that,” said Hallahan. “So it’s been a great experience working with Caroline to get them thinking not just about the technology element, but the people and the cultural part of that transformation.”

At the start-up/scale-up level, Hallahan is involved with digital therapeutics company Beats Medical, headed by Ciara Clancy, and FoodCloud, whose CEO is Iseult Ward. You’re probably noticing a pattern here. “I’ve got a little bit of a trend of working with young female CEOs who I’d like to help invest and scale, and they’re fundamentally technology companies,” she said.

“The platform that FoodCloud has created is now being piloted in South Africa. It’s being used by other food banks around the globe. And they have a big ambition to really look at the whole ecosystem around surplus food and how do we make Ireland an innovation hub for that.”

As for Beats Medical, Hallahan has invested in it personally. “I’m also chairing their board and spending a lot of time with Ciara,” she said. “They’re at the stage now where they’re working with large pharma. So we’re looking at the commercial side of the business, the people strategy and then looking at VC investment into the business to help it scale and grow.”

Hallahan is clearly relishing her new role as board member, advisor, investor and sponsor of young leaders. Other roles include being on the public interest body for PwC, created by the Central Bank and the regulator at the time when the banks were in trouble, and question marks arose over the auditing and risk management by the Big Four firms.

“Interestingly, PwC have opened that up to all parts of the organisation, not just risk and assurance, but also the consulting side. So we’re getting to meet some of the key clients, the employees, new partners, senior managers, and really looking at the culture of the business and the compliance, in the public interest, so that’s a really different one.”

Hallahan also joins the board of hotel group, Dalata, as the first wave of non-executive directors step down since becoming a PLC, and founder Pat McCann steps back. She’s hugely impressed with their record on people development. “They’ve had about 12 general manager changes in the past 12 months or so, and their leadership team changed, and all those people have been grown and groomed internally. They have a very structured people focus, so you go in there at entry level, and can work your way right up to leadership,” she said.

It’s something Hallahan knows all about, given her own career trajectory at Microsoft, but it’s well worth watching the video to hear about her remarkable journey in her own words. An inspiration for any person hoping to gain a foothold in our competitive sector.

This is the sixth in our Conversations with Leaders series. Watch out for our upcoming instalment with Paul Rellis, CEO of Viatel Technology Group.

Ann O’Dea is the CEO and co-founder of Silicon Republic and the founder of Future Human