Anne O'Leary reflects on her “no-regret” career moves, the power of human empathy in an AI age and why wearables are “Europe’s smartphone moment”.
There is a specific kind of quiet courage that defines some of the most outstanding women in business. It is not the loud, boardroom-thumping variety, but a steady, sustainable and rhythmic bravery, the kind that allows a person to stand at the edge of the unknown and simply say yes.
This bravery is clearly evident in the career journey of Anne O’Leary, from her early days in telecommunications at BT and a 14-year tenure at Vodafone, including nine years as CEO, to Head of Meta Ireland. As she prepares to accept the Lifetime Achievement Award at the 2026 IMAGE PwC Businesswoman of the Year Awards in May 2026, Anne isn’t looking back at a static legacy when she casts her eye over her career. Instead, she is reflecting on what has been less of a ladder and more of a series of daring, deliberate leaps, from the early dial-up days of telecommunications to the high-stakes frontier of AI.
From ‘know-it-all’ to ‘learn-it-all’
Reflecting on her career, Anne says her understanding of what makes a leader effective has been “completely transformed”. In the early stages of her career, she admits to falling into the trap of thinking a leader needed to be the “person with all the answers who could direct from the top”.
However, leading over 2,000 people from 112 different nationalities, as Head of Meta Ireland and VP of Mid-Market SMB Group EMEA, has taught her otherwise. “I’ve learned that the era of the ‘know-it-all’ leader is absolutely past,” she says. “The pace of technological change driven by AI requires us all as leaders to be lifelong learners – I like to call it a ‘learn-it-all’ mindset.” For Anne, this era demands that leaders listen more, ask better questions and collaborate more effectively, as “no single person can possibly have all the answers”.
She emphasises that effective leadership today is about “creating space where innovation can flourish”. In her view, the best breakthroughs occur when teams are empowered to “experiment, ask questions, and even fail forward without fear of reprisal”.
Bravery and the ‘benevolence bias’
Anne is a staunch advocate for “being brave and pushing ourselves beyond our comfort zones”. She often speaks about the “incredible opportunities” that arise from simply saying “yes” to daunting challenges. Yet, she warns of a subtle obstacle she calls “benevolence bias”, when those closest to us urge caution out of care. She insists it is vital to “trust ourselves to take the longer, more challenging road”.
Her advice to women starting in the technology sector is rooted in this same spirit of boldness. “Go for that role, take the leap, and be brave in your career ambition,” she says. She often relies on a personal mantra: “What would I do if I wasn’t afraid?” She believes that “people often regret the things they didn’t do rather than the things they did do”, noting that every major move she made was a “no regret” decision that defined her success.
People often regret the things they didn’t do rather than the things they did do.
AI: The once-in-a-generation chance
Rather than viewing AI as a replacement for human talent, Anne sees it as a tool that amplifies “uniquely human skills”. By embracing AI to automate repetitive tasks, businesses can free up teams to focus on “creative and strategic work that really moves the needle”.
“As AI takes over the routine stuff, it actually makes our uniquely human skills even more valuable,” she explains. “That’s why we need to keep investing in upskilling and reskilling, especially in areas where women often shine – creativity, empathy, critical thinking and emotional intelligence.”
Championing the Irish entrepreneur
In her role overseeing Mid-Market and SMBs for EMEA, O’Leary sees first-hand how Ireland’s business community is “bursting with creativity and ambition”. She views AI tools like Meta’s Advantage+ suite as a way to “level the playing field”, allowing smaller businesses without big marketing budgets to compete with global peers.
“For Irish SMBs, these tools mean you can deliver highly personalised ads that reach the right people, at the right time, and in the right place, whether that’s in Dublin, Donegal, or Dubai,” she says. With Meta’s platforms linked to €6.3 billion in economic activity in Ireland, her message to entrepreneurs is clear: “The world really is your oyster”.
The future: Europe’s ‘smartphone moment’
Looking ahead, Anne is most energised by the potential of AI wearables, specifically Meta’s AI glasses. As a regular cyclist and swimmer in West Cork, she uses her Oakley Meta Vanguards to capture hands-free content and manage calls on the go.
She believes this technology could be a turning point for the continent. “Wearables are one of those rare spaces where European companies… are actually leading the way on a global scale,” she says. “Honestly, this could be Europe’s smartphone moment.” With Meta’s Reality Labs facility in Cork focusing on next-generation display solutions, she is proud that Ireland has a “central role” in this mission.
The impact of recognition
For Anne, being announced as the winner of the Lifetime Achievement Award, to be presented at the 18th annual IMAGE PwC Businesswoman of the Year Awards in May 2026, is “both humbling and energising”. She views such accolades not as personal trophies, but as “a celebration of the collective effort it takes to drive change”.
“If these awards encourage even one more woman to go for that next role, to take a leap, or to believe in her own potential, then they’ve done their job,” she concludes. “And that, to me, is the real impact of recognition.”
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