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A Tighthead in Tech

Conán O’Donnell was pulling pints in the foothills of Mount Maunganui on New Zealand’s North Island when his phone began to ring. An unknown Irish number.

Slightly bemused, he answered with his customary good humour. In his new life, the phone usually rang for one of two reasons: his mother wanted to check in; or a rugby club somewhere in the world needed a prop in a hurry.

Once the Sligo man left Ireland for Japan and proceeded to loop around the world several times, opportunities had a habit of appearing out of nowhere only to disappear again just as quickly.

This one hit a little differently though. Connacht Rugby wanted him back in Galway.

And there, in the middle of a beach town on the other side of the world, with sand still clinging to his toes and dirty glasses waiting on the counter behind him, O’Donnell found himself facing the very thing he had once thought he wanted most.

When Connacht first told him his contract would not be renewed in 2019, the then 23-year-old left carrying the sort of quiet fury professional sport specialises in creating. As he walked out of the gates at the Sportsground, he made a promise to himself that he would tog out for the province again, and prove a point.

Yet when his route back to Galway opened up, something within had changed. By 2022, and having played rugby in Italy, the United States, Argentina, Japan, Australia, South Africa and New Zealand, rugby had stopped being the centre of his world.

Somewhere between the short-term deals, landscaping jobs and couch-surfing he had stumbled upon a realisation that life held so much more for him than rugby was willing to offer. The old ambition that held since his schoolyard days in Sligo had loosened its grip.

So O’Donnell thanked them for the offer, and got back to serving drinks.

Here was a young Irishman who was as far from home as you can get, discovering that real freedom can sometimes arrive disguised as disappointment. The real turning point was realising that rugby no longer got to decide everything.

Nevertheless, O’Donnell continued to carry his boots wherever he went. Contracts still landed, but rarely long enough to stretch reassuringly into the future. He became part rugby player, part labourer, never entirely sure which version of himself he would be from one week to the next.

One such week he was landscaping in New Zealand, working for an elderly man who informed anyone within earshot that the Irish lad was a bit useless. Mercifully for both his employer and New Zealand’s horticulture, O’Donnell’s gardening career lasted all of three days.

“I had been out of contract for a while at that stage so I decided to let loose a little bit,” he remembers with a hint of divilment. “There was no hint of anything in the pipeline and it was probably the first time in years I felt I could totally relax, so I went out with a few pals and left the phone at home.

“When I got back in the early hours, my housemates came flying down the stairs shouting and roaring. The Highlanders coach had been trying to ring me because they needed cover for a concussion injury in Argentina. So I grabbed the bag the lads had packed for me and headed straight to the airport.”

Another time he was moonlighting as a painter when the Crusaders came calling. And so his twenties became a patchwork of short-term propping deals, mixed with stints as a teacher’s assistant, a dishwasher in Queenstown and eventually a barman in Mount Maunganui. The rugby came and went as though the game itself couldn’t decide what to do with him.

Undoubtedly enjoyable, professional sport can also become all-consuming when every breath and decision revolves around it. Competitive people are conditioned to believe happiness lies at the next step. They relentlessly chase another cap, another contract or another season. And yet their sense of identity can become tied to whether a coach happens to fancy them on a Thursday morning.

O’Donnell had lived that life in Galway. Even as he drifted in and out of favour, there was nowhere else in the world he would rather have been. Yet the further his travels took him, the more the fondness began to soften. Indeed, by the time he was togging out with the Toronto Arrows, he already knew something fundamental had shifted.

“I could’ve kept playing,” he says assuredly. “There’s always somewhere to go if you want to keep saying you’re a professional rugby player. But I was nearly 27 and I just thought: do I actually want this badly enough anymore?

“When I was younger, all I ever wanted to do was to play for Connacht. I loved every minute of it until the day I had to walk out those gates with a big lump in my throat and a chip on my shoulder. To be honest, I hadn’t seen the end coming. I thought I was tipping away nicely.”

When the chance to prove his point arose then, you’d have thought O’Donnell would have sprinted home in his tongs. Instead, he drew a metaphorical line in the sand that surrounded him, marking the beginning of everything else.

“I was just really, really happy,” he says. “That’s probably the simplest way of putting it. I was living in this little beachside town, surfing a bit, training away, doing a bit of work and enjoying life.

“There were plenty of conversations about going back into full-time rugby. I even got a phonecall from Andy Farrell about linking up with Ireland when they were down there in 2022 but I couldn’t bluff my way through a cheekbone injury. I get a mention in his book for that, actually!

“So I had plenty of options if I wanted them, but when Connacht called, I just didn’t feel the pull I thought it would have.”

O’Donnell is remarkably open about his experiences. The ambition that once consumed him now seems softened by perspective, and by enough distance to appreciate the absurdity of his circumstances.

When he finally returned home to Ireland, the landing was hardly glamorous. He moved back in with his parents in Sligo, signed on the dole and tried to figure out how the ordinary working world functioned. He moved to Dublin.

“I can clearly remember myself and Conor Phillips collecting our social welfare cheques together,” he remarks. “He’s not done too badly but I think a lot of people assume that once you’ve played professional rugby, you’re made up. The reality is that the game can leave you standing still while everyone else is moving on.

“Thanks to a contact, I managed to find some work in Dublin. It was a brilliant opportunity but pretty quickly, I knew it wasn’t for me. Don’t get me wrong, I was very grateful and fortunate to have landed that role, but I couldn’t get my head around the way everyone worked.    

“When a sportsperson shows up for work in the morning, they’re expected to be hydrated, fed and stretched. The natural thing for me was to apply the same principle to my new job. After a good gym session and breakfast, I’d be sitting at my desk by 08.30am eager and ready to go because that’s what rugby conditions you to do.

“Then nine o’clock would roll around and lads would stroll in at quarter past with coffee chatting away about this and that, inviting me out for another.”

At first O’Donnell was fascinated by the novelty of it all, but soon the culture shock wore thin.

“There were days where I literally had no work to do and I’d just sit there, tapping away on my keyboard, pretending to work for hours,” he admits. “Coming from a really structured, competitive and target-led environment, I found that really unstimulating.”

He discussed this challenge at length with some of his former teammates. The more he spoke, the more he was nudged towards tech sales, an idea he initially resisted. Yet they persisted, explaining that a lot of what makes rugby players survive actually suits that environment.

Encouraged by their reasoning, Conán O’Donnell applied for a position in Stripe. He reached out to Jamie Heaslip and discovered that Tom Daly, his former Connacht Rugby teammate, was due to start with the company. And as it turned out, sales suited him perfectly.

“My manager actually said to me one day: ‘I’ve never seen someone handle rejection so well.’ I hadn’t even noticed. Getting a ‘no’ over the phone is nothing compared to meetings with coaches telling you you’re involved, or worse – not being kept on. In that sense, someone declining a meeting isn’t going to break you.”

Now thriving in Stripe’s enterprise growth division, O’Donnell recently won the 2026 EMEA Q1 award for ‘Delivering Outstanding Results.’ He has to be reminded of that fact, perhaps the strongest sign yet that he no longer feels the need to prove anything.

That freedom seems to have opened other doors too. Indeed, since stepping away from the game he has drawn up a bucket list of things he’d like to do before turning thirty. One of them was to perform in a musical. It’s a box he ticked recently with the Glencullen Dundrum Musical & Dramatic Society… despite not being able to act, sing, or dance.

“My brother is into theatre so I said I’d give it a go and spend a bit of time with him. The first day they were all doing icebreakers and acting games and I remember thinking: ‘Jesus Christ, what am I after getting myself into here?’”

“It was just brilliant craic though,” he notes. “People from all ages and backgrounds coming together – a bit like some of the dressing rooms I was in! I definitely grew into it, and the cast used to joke that my lines kept getting longer every week because I was trying to make the most of my time on stage!”

Perhaps that is the real lesson in O’Donnell’s story.

Somewhere between Galway, Christchurch, Queenstown, Toronto and Mount Maunganui, rugby gave him enough to keep dancing while he figured things out for himself.

Sometimes, the brightest lights are not the ones you spent your whole life chasing.