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Meet the Trainer... Aileen O'Toole, Chartered Director & Digital Strategist

Posted By Learning & Development Team, Monday 29 April 2019
Updated: Thursday 25 April 2019

What do you do as a Digital Strategist and a Chartered Director? 

I’ve a portfolio career with three elements – digital strategy assignments, non-executive board roles and pro-bono commitments.  My digital work focuses on supporting leadership teams to plan, deliver and troubleshoot ambitious digital projects that support their business strategies.  My board roles involve helping to formulate strategies and having oversight of their implementation by executive teams while my pro bono roles are about causes that light my fire.


What were your key career moves to get to your current role?

I am a former business journalist and Editor. I took an entrepreneurial leap in 1989 when I co-founded The Sunday Business Post where I combined my part owner/Executive Director/Company Secretary role with editorial management, and an involvement in the marketing strategy that ultimately created a strong media brand. 

Three years after the newspaper was sold, I wanted a fresh challenge outside of the media sector and established Ireland’s first digital strategy business in 2001. That has been like three separate start-ups in one, as I’ve had to pivot the business to respond to digital changes, client requirements and where I can add the most value.  I’ve combined this with non-executive board roles and in 2016 I qualified as a Chartered Director.


What is the biggest challenge you face in your role?

Staying up to date, relevant and strategic.  Given the fast pace of change in digital technologies, I’ve to constantly upskill and stay on top of trends.  I see my role as enabling my clients to be both future-focused and make strategic decisions. Right now, for example, clients need to be considering how emerging technologies like artificial intelligence and blockchain will impact on their sectors and their businesses.  They also need to avoid the many temptations to invest in “shiny new digital things” that may not deliver any long-term business value.  Instead, they should have a clear vision of how digital can deliver on their business strategies and then be able make informed investment and people decisions.


What key skills do you need to be effective in your role?

Firstly, it’s necessary for me to be strategic and concentrate more on what is of most importance to the long-term success of the business, instead of being buried in the entrails of a digital project.  Communications skills are vital.  For many senior leaders, techno babble is a turn off so I need to translate the jargon into business speak and make it all relevant and accessible to everyone. 

Digital projects are really change management projects and taking a customer perspective helps to get an understanding and buy in to change.  Similar strategic, communications, technical and other skills are also relevant to board roles.  Given my portfolio life, I have to be highly organised in how I manage multiple complex projects and other commitments concurrently. 


Describe a typical working day.

It very much depends on the mix of client commitments, board and pro-bono activities I have on a given day.  I might be facilitating a digital strategy workshop, commissioning or analysing research or managing a vendor selection process.  If I’ve an upcoming board meeting or board committee meeting, I’d have to spend a lot of time reading and annotating the board pack.  As a non-accountant, I can’t simply skip over the sometimes voluminous financial data as board members without accounting qualifications are as equally responsible for the oversight of the financial performance as those with such qualifications. 

I’ll also have to make time for pro-bono commitments, which at the moment involves a female leadership initiative I co-founded and mentoring some young professionals. There isn’t a day goes by without me consuming a lot of media – traditional and digital – and sharing content on my social media accounts.


What do you love most about your role?  

Variety.  The mix of what I do is ever-changing between different sectors, businesses, teams and suppliers. Because I’ve worked across all sectors, and am completely independent, I can often make a breakthrough by applying an approach that works in one sector to another one.  I also love achieving a tangible result arising from my work or my input into something.  That result may be hugely significant to a business, like the successful entry into a new market, or to an individual, like mentoring them to successfully transition to a new career.


Looking ahead, where might your career path lead to next?

I’m about to embark on a process to help me to answer that very question. Every few years, I take a step back and with professional help try to envision what I might do next.   In the past, this has helped me make some big career decisions, like leaving The Sunday Business Post and taking time out to pursue a corporate governance qualification. It’s also helped me shed some of the work I no longer find challenging and identify new potential areas of opportunity. At this stage, the changes are more evolutionary than revolutionary.


Aileen O’Toole is facilitating the Marketing Institute's CMO masterclass, Increasing Marketing's Influence in the Boardroom on 28th May. More details on

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