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Leadership Lessons: Interview with Ruairí Conroy, Site Lead for Diligent

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In the latest instalment of our Future of Work Interview Series, Barry Winkless, CSO of Cpl & Head of the Future of Work Institute, spoke with Ruairi Conroy, Site Lead for Diligent in Ireland, about his career journey to date and Diligent’s exciting expansion in Ireland.

Ruairi, you are relatively new to Diligent, can you tell us more about what attracted you to the company and why it was the right next step in your career?

I think one of the big things that stood out for me is Diligent’s commitment to growing in Galway and engaging with the local community. I think community is a big theme with Diligent both within the office and virtual offices as we have right now and with the charities and businesses in the locations that Diligent has a presence.

Also, being from the west of Ireland and having worked in Galway specifically for nearly five years, I believe that the talent in Galway is world-class, and that was one of the big things that tipped it in favour of Galway for Diligent in the first place. Pretty much a year ago to the day, I had the chance to meet with my now boss, Lily Haskins, and a number of the executive team in Diligent along with Ricky Conneelly from the IDA who had set up an executive lunch to help Diligent understand a bit more about the locality.

I was really blown away by the ambition, not just as a company, but the ambition they had for Galway, and how Galway could be a catalyst for a transformative period in Diligent’s story. I am really excited about the next steps.

Ruairi, from our own conversations I know that you are a proud Mayo man and you’ve had quite an interesting career journey to date. Can you tell us a little more about the interesting path that led to Diligent?

Absolutely, as you said, I'm proud to be a Mayo man. I'm from a Gaeltacht area on the shores of Lough Mask. I had a great upbringing and in a beautiful part of the country. I then went to not quite the Big Smoke, but maybe the Little Smoke in Limerick to attend university, where I did an IT and telecoms degree and then to the Big Smoke eventually, Dublin, to do an advertising and e-commerce post-graduate.

It was on the back of that, that I secured my first ‘big boy’ job in 98fm which was a huge culture shock but one which I thoroughly enjoyed. I spent six years there, and I was lucky enough to start off as a junior account manager and ultimately moved on to lead the sales teams in 98fm and Spin1038 for a couple of years before moving to Google in 2008.

I spent nearly five years in Google and for the first six months, I thought a lot about, and actively tried to leave Google. I found it to be such a cultural shift, coming from the emotionally charged and personality-driven environment of radio, into probably the most data-driven organisation in the world. I did very well in the radio business because I had more of an analytical and technical way of approaching sales and, strategy and I led by teaching.

Then, I went into Google, and overnight I had eradicated my unique selling point of being a leader. I felt like an imposter for quite a long time, trying to lead a team of really experienced, digital salespeople and I didn’t have that skill set.

It took several months and a mentor to flip my mind about it staying in the role. Google had recently acquired YouTube and while it was the number one game in search, it had only really scratched the surface in terms of display and was really looking up to you Yahoo at the time. Then when 08/09 hit, there was a flatlining in the economy full stop, and search advertising was plateauing. So certainly, I think my storytelling and benefit selling skills from my radio days came into play to help introduce some transformative measures of selling something relatively new.

I had a great time, but I left Google temporarily when my dad got sick with a heart attack at the end of 2009, and I went back home. A few months later, and four stints later, however, he told me to get out of the house and go back to Dublin. It was a case where I was always welcome but only in short stints!

I went back up to Dublin and I was lucky enough to interview for three jobs again with Google. I went on to lead a couple of sales and account management teams there until 2013. And then the Head of Sales for North America in Google moved to a company called AdRoll and asked me to move over to help set up their operations in Dublin. I moved there in September 2013. AdRoll was a rollercoaster, to say the least. I had some great days there but also some of the toughest days both personally and professionally.

They had just received a large round of funding, and we were scaling quickly. We hired 100 people in the first 18 months, and we opened offices in London, Tokyo, Sydney. I learned a lot along the way, but I think it helped me to take a step back and realise what is most important to me personally, and that was family. We made the decision, then in 2015, to relocate back to Mayo, where we now live. And I continued with AdRoll for another six months before joining SiteMinder in Galway.

Two hours into my first day with SiteMinder I was on a stage in front of dignitaries, RTE, and different media outlets to announce that we were bringing 100 new jobs to Galway. I was just hoping that no one would ask me any questions about SiteMinder! I was with my then boss Dai Williams, and he was someone I still consider a good friend and someone who was a great mentor all the way through.

I started in SiteMinder as the Site Lead, and we hired 100 people in 100 days which was an excellent experience. I then managed to lead a few different roles within SiteMinder, most recently the Inside Sales Global Leader up until joining Diligent. I would not change anything about my career journey, it was definitely a tricky and challenging route but one that I gained a huge amount from which hopefully I can put into play in a positive way with Diligent.

Can you tell us a bit more about Diligent as an organisation and what the role of the hub in Galway will be in the overall Diligent global network?

In essence, Diligent helps board directors and executives make better decisions and govern organizations using data analytics, insights, and secure collaborative tools. We have the largest global network of executives and directors and are relied on by 19,000 companies and 50% of the Fortune 1000 companies, and with nearly 700,000 leaders in over 90 countries.

We are a company that happened, a bit under the radar in some capacities, building quite a significant business. Last month, we had two recent acquisitions of Steel Corp. and Galvanize, which now makes us the biggest player in governance, risk, and compliance globally.

Galway is going to play a huge part in that expansion and transformation of the business. We are committed to hiring 200 people this year since we announced our entry into Ireland in November. By the end of this month, we will have 100 people employed locally for Diligent, so we're on track to reach our 200 goal by the end of the year.

Another thing that attracted me is the breadth of roles that we are hiring for and building out of Galway. We are scaling a 360-operation including customer success, finance, HR, and product. I'm genuinely blown away by the talent that we've been able to attract, and we've certainly got a team of A-players. I often say to surround yourself with people that are smarter than you and I am well down the pecking order when it comes to smart people in Diligent.

I think when it comes to building a culture and setting the foundations of any business, people are that critical component and we've been able to hire and attract some of the best and brightest out there.

What are the leadership lessons you will take into Diligent?

I think, first, and probably the most attractive trait for me personally and professionally, is authenticity. I think it is the critical component of building trust. From my perspective, you should be the same around the CEO of the business as you are around anyone in the business.

We have set ourselves a pretty difficult challenge of scaling an operation in a fully remote environment, and, if you don't have that authenticity, and that ability to connect with people, then those types of aspirations are certainly incredibly difficult to achieve successfully.

Secondly, I would say, being emotionally connected to what you do. You can work for the best company in the world with the best products but if you do not care, then as a leader you are not going to get your people motivated enough to care either. You need to be more passionate about what you do, because, at the end of the day, that is contagious. That is the type of environment that I've always reacted very well to, and it's one that I've tried my best to create as well.

Thirdly I would say is, talk less, listen more. Surround yourself with great people and listen intently and purposely to what they have to say. Involve others in decision-making as I think that helps to share accountability and build huge camaraderie with teams. I think there is a negative perception that accountability means extra pressure but, I think when you involve people and give them extra accountability and responsibility, people rise to the challenge and productivity can soar.

Finally, it is all about people and culture, and ensuring that you hire people that have the competencies to do the role, but also the potential to do great things in the future. My role is to create an environment and culture for people to truly go on and do phenomenal things for themselves personally, and for the business professionally. It is about creating the environment for Team Diligent and Team Galway and that is certainly something that I'm very, very passionate about.

What is the big opportunity for Diligent as an organisation, and Galway as the hub, now and in the future?

I think a big piece we have been focused on over the last number of months has been the onboarding and early-life experience for people joining Diligent. We've been lucky enough to work with a really talented group called SYPartners, a third-party consultant to help us rethink and redesign that new starter journey that we piloted globally, and in recent weeks have used with new hires in Galway.

I think for new hires, there is a huge anxiety when joining any business at the best of times and in the current environment that is heightened. We miss those personal contacts and visual cues that only in person can bring. So, I think there is a big responsibility on us as employers to try and alleviate that anxiety and help people bring their best selves to the office as quickly as possible.

Secondly, there has been a big focus on working with partners locally. I am lucky to lecture in NUIG which is a great organisation with phenomenal staff and students, and I think continuing to build relationships with educational institutions and other partners within the locality is a priority. Also, working with different charitable bodies to really walk the walk, when it comes to community is certainly a big aspiration that I have for the Galway office.

Interested in a career with Diligent?

The company is currently hiring across several specialty areas for their European hub in Galway including product, HR, marketing, and customer success. Learn more about Diligent in Galway