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Five Questions with… Siobhan O’Reilly, UK Country Manager, Dropbox

Every Monday morning we fire five questions at a leader in business technology. Today we’re joined by Siobhan O’Reilly, who leads UK operations for Dropbox.

Siobhan – What’s the Biggest Challenge for your Clients?

Given the current situation, many of our clients are encountering challenges around moving to a distributed workforce. Regardless of a business’ size, going from a scenario where people regularly congregate in one physical space, the office, to one where many are logging in remotely is bound to involve new and potentially daunting processes.

We’ve worked closely with customers to help them navigate this novel terrain and identify ways of working that can help them retain a collaborative and creative energy, while making them faster and more responsive. Whether that’s developing new digital workflows that enable people to work together on a design, or a tool that makes it simple for managers to put their e-signature on an important document, there’s many ways we can make this unprecedented situation smoother and more enjoyable for all workers.

Technology that Excites you Most?

It feels like many of us are in an experiment with working from home right now, and I’m really curious to see what comes out of this experience in the longer term. These new ways of working open up novel possibilities for all kinds of technologies – the ones that strike me in particular are Augmented Reality (AR) and Virtual Reality (VR). While these technologies have been around for a while, and discussed a lot, this could really be the time for them to flourish. For example, a distributed workforce could harness the power of VR to all meet virtually, collaborating in the cloud and getting work done, while still having that sense of togetherness that an office can bring.

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Greatest Success?

I’ve lived in several countries over the course of my career, which have brought their own obstacles and opportunities, whether that was New York, San Francisco, Luxembourg, Dublin or London. As time moves on I see now just how valuable they were, not just for my career progression, but also in giving me different lenses to look at life through. However, looking back, all of these brought about their own set of challenges and life changes that I had to learn to navigate.

I would say my greatest success was learning to build resilience and persevere through the challenges these changes brought. Whether that was navigating the ups and downs of growing new teams, learning the nuances of new markets, or building relationships and finding common ground with people from completely different cultural backgrounds and upbringings.

Worst Failure?

As with most failures, mine turned out to be a blessing in disguise. In the early stages of my career, I worked in the world of financial services.

Excited by the idea of working somewhere different, I moved to Luxembourg to take on a job that simply did not suit my skill set. I didn’t enjoy it, but I also wasn’t very good at it, nor did I find it particularly interesting. Although I loved the country and the friends I had made, the job just wasn’t the right fit for me. This was a pivotal moment in my career, as it showed me how important it was for both my skills and passions to be aligned to what I was doing. I was lucky enough to learn this tough lesson early on in my career as it enabled me to make a change into the world of technology where I’ve been for the last 12 years and never looked back.

In Another Life I’d Be…

One of my big passions growing up was dancing, and in fact, following the period of time when I had left my job in financial services, I went back to do a Master Degree in Dance – it’s therefore maybe possible to say that in another life I would be a dancer!

See also: The Big Interview – Bill McDermott on Life After SAP and Midnight Note-Taking


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CBR Staff Writer

CBR Online legacy content.