Growing a Company Means Growing as a Leader

What does it take to build a company that lasts? And how does your role as a leader change as the business grows beyond the team you first set out to build?

These were some of the questions explored at Endeavor Ireland’s first event in Galway, hosted with our friends at PorterShed. Anne Heraty, founder of Cpl and a founding Board Member of Endeavor Ireland, joined Emma Redmond, Head of OpenAI Ireland and a proud Galway native, for a fireside chat moderated by Niall Horgan, co-founder of Gym+Coffee.

Anne started Cpl in 1989 with a PC, a database and an idea about how recruitment could be done better. Over the following decades, she grew it into one of Ireland’s leading recruitment and employment services companies. In 1999, she became the first woman to lead an Irish publicly listed company when Cpl floated on the stock market. In 2021, the business was acquired by Japan’s Outsourcing Inc. in a deal worth over €300 million.

Emma’s journey has taken her from practising law to roles at LinkedIn and Stripe, before becoming OpenAI’s first employee in Ireland and helping establish its presence in Europe. Today, she leads a team within one of the world’s fastest-growing technology companies.

Their careers have taken different paths, but both have experienced what it means to lead through significant periods of growth and change. Their discussion offered a practical look at the decisions, people and personal adjustments that come with scaling a company.

Knowing when to let go

When Anne started Cpl, she was closely involved in almost every part of the business. With a team of 10 or 15 people, that approach worked. But as the company grew towards 50, she could no longer make every decision herself.

The transition required a different level of management discipline. People needed to understand what was expected of them, what success looked like in their roles and where their particular strengths could make the greatest difference. Anne also spoke about recognising that when someone wasn’t performing, it didn’t necessarily mean they weren’t capable or committed. Sometimes, the role simply wasn’t the right fit.

Letting go of decisions was one part of the challenge. Learning to build a team that could operate effectively without her involvement in everything was another.

That transition wasn’t always easy. Anne reflected on the personal difficulty of having to let people go, particularly in the early days, and the questions those decisions raised about whether she had made the right hiring choices in the first place. As a founder, the responsibility for getting those decisions right is never far away.

Her experience navigating the public markets brought another dimension to that responsibility. Cpl floated in 1999, and when the market collapsed in 2001, the mistakes and challenges facing the business were suddenly visible to everyone. Anne described how quickly she had to learn and develop resilience, with the added pressure of knowing people were watching.

Growing a team without losing its culture

For Emma, leading within a company growing at extraordinary pace brings a different set of challenges. At OpenAI, teams are expanding, responsibilities are evolving and the organisation is changing quickly. As a leader, maintaining a sense of connection and shared purpose becomes increasingly important as more people join.

Emma spoke about the importance of creating opportunities for people to connect beyond their immediate teams. Shared lunches brought colleagues together and gave them a chance to hear what others were working on, often creating opportunities for collaboration. Coffee walks became another way for people to get to know colleagues they might not otherwise spend time with, particularly as the company returned to the office after COVID.

These simple routines helped bring people together as the team grew. They also reinforced an important point: culture doesn’t look after itself. Leaders need to be intentional about the values they want to build, model the behaviours they expect and keep communicating what matters.

That becomes particularly important as a company expands. The informal relationships and ways of working that come naturally in a small team need more thought and attention as the organisation gets bigger.

Ambition has no fixed path

Looking back on her journey, Anne reflected on how Cpl’s growth had taken a different path from the one she might have imagined at the beginning. There were unexpected turns, difficult decisions and opportunities that emerged along the way. Her advice was not to put a ceiling on ambition or treat early targets as the limit of what a company could achieve.

Emma’s experience offered another perspective on navigating an unpredictable business environment. Both highlighted the importance of relationships, trust and the ability to get things done through other people. For leaders, building a strong network isn’t simply about who you know. It’s about developing genuine relationships and getting involved in areas you care about.

Anne also spoke about the importance of staying visible as a leader. The relationships you build with your team during the good times matter when difficult decisions need to be made. Regular communication and trust create a foundation that leaders can draw on when the business faces challenges.

Across their different journeys, one idea came through clearly: building a successful company requires more than a strong idea or a good opportunity. It takes the willingness to keep learning, adapt as the business grows and give other people the space to succeed alongside you.

A big thank you to Anne, Emma and Niall, the PorterShed team and everyone who joined us for our first event in Galway. It was a pleasure to bring together such a brilliant group of entrepreneurs and celebrate the ambition and talent across the West.