The Most Important Decisions I Have Made as an Entrepreneur

Gerry Brennan, CEO of Cloudbooking

When I came up with the idea for Cloudbooking, my vision was to create an effortless method of managing workspace. Being the holy grail for property managers, it matches their need to manage space effectively and obtain meaningful data.

Get a free demo

Enquire about a no-obligation demo today and get an exclusive hybrid working research paper for free. Created in partnership with YouGov, this invaluable guide provides essential insights into developing your own effective hybrid strategy. Click below.

When I came up with the idea for Cloudbooking, my vision was to create an effortless method of managing workspace. Being the holy grail for property managers, it matches their need to manage space effectively and obtain meaningful data. It will give their colleagues the ability to get on with their workday without having to actively engage with software in order to utilise available spaces and services. Whilst Cloudbooking has achieved this, it hasn’t been easy!  I have made some wrong decisions and learned some lessons along the way. I don’t think It would have been possible for me to do it without my team. Whilst the entrepreneur has the idea, the real challenge is working out how to instill that same vision and passion in their team and create an environment for everyone to strive to make that idea a reality.  So, what lessons have I learned along the way and which decisions have paid off? 

The Cloud

The first risk that I took was deciding to put everything in the Cloud, only it wasn’t called the Cloud back then because that had not been invented. We were genuine SaaS pioneers back in the early 2000’s while our competitors were client-server. However, I could see the value in hosting a service that continually evolved and could be supported from anywhere.

That led to Cloudbooking employing home-based support staff.  It gave us access to a huge talent pool of people trapped by their own domestic circumstances, but with great skills to offer. Although we have an office in the heart of London, many of our staff work from home and use the office when they need it. It also led to us rebranding as Cloudbooking in 2013. I purchased the dot com domain before changing the name of the company.  We then rebranding everything as Cloudbooking – which really reflects what we do in every sense.  

Homegrown talent 

Quite early on I made the decision to take development in-house and only hire UK-based developers. This is because I wanted to be able to work alongside the development team and guide them. Whilst I am not a developer, I understand the entire process of development and what is possible and like to keep challenging boundaries and leveraging code to develop really smart solutions. We thrive on new development and release updates to the system all the time and aim for at least one major release per month. The system we have now is entirely built on my own experience and knowledge of this market and the lessons we have learned from the millions of bookings we process.  

Grow organically 

Some would say it’s a risk, but I have not sought external VC investment for Cloudbooking because I want to continue to grow it organically and keep faith in the ideas and solutions that have taken us this far and to keep control in the hands of the management team, who understand the culture and strategy. Everyone has share options, which means we all have a stake in the future success of Cloudbooking and have a level of control over our direction of travel that none of our competitors have and we can shape our products around the feedback from those very clients that are helping us to grow. That is very important to me.  

API integration

As an entrepreneur, a big decision I have had to take is the choice to build the new system based on an open API integration strategy. This will allow us to expand our functionality by partnering with services that complement ours. We don’t need to reinvent or build products that already work amazingly well. A good example is our integration with multiple sensor partners to obtain and display real-time occupancy data from sensors and allow people to book based on that data. Also, future integration with Google Maps, TFL, Highways Agency and other travel related services, will allow us to monitor traffic and travel and then help our users manage their day. It will also allow us to find them alternative spaces and work out ways around the issues they are going to face before they even know they have problems!   

Client care

I have always said that no matter how large we become, I want each and every one of our clients to feel like they’re number one. That’s why when I signed a large deal with HBOS back in 2007 and had a choice to either send a template form to every site around the country and get them to send me their rooms, desks and other key information so I could build their sites without talking to them, or visit all 125 locations personally and build a system that was unique to each site, so I chose the latter. The fact that we have retained this client ever since (and eventually replaced the system that Lloyds Banking Group were using when they merged with HBOS in 2009) suggests it was the right call! This is the reason why we pay so much attention to every client.

Finally, the hardest part of being an entrepreneur has been to step back and give others more responsibility and remove myself from everyday tasks. I have seen our people develop and thrive and because of this Cloudbooking has such a wonderful team that it feels more like a family than a business. It doesn’t mean that I am not engaged in every aspect of the business, but I like to empower my team and encourage them to believe in their abilities and trust their instincts. After all, being a successful entrepreneur these days is also about having the right people around you. 

By Gerry Brennan

Like this article? Spread the word

Want to hear more? Never miss a Cloudbooking post

We promise not to pester so get the best of Cloudbooking straight to your inbox, once a month!

Try Cloudbooking today

Request a free, no-obligation demonstration and let us show you how our system can benefit your organization.