Greg Sheehan, Founder and CEO of PlayBooks

We caught up with Greg Sheehan, Founder and CEO of PlayBooks to learn a little more about his career journey, what led him to attacking the problem he and the team at PlayBooks are trying to solve and what the future has in store. Greg also shares his insight into the importance of communicating honestly with the people around you and building a culture of trust. Thanks for sharing your story, Greg.

How would you explain to a five year old what you do?

We make software that helps you look like the smartest person in the room.

And for the adults, what does that translate to in regards to your day-to-day?

As the Founder, I lead a team of talented folks that are hustling to build and sell our early versions of a globally changing software platform, which aims to “bring the world’s best expertise into every meeting”.

We’re building a marketplace that firstly makes running meetings easy and effective and secondly allows others to connect into your discussions, just as the thing they specialise in is being discussed - thereby creating a new e-commerce channel where “the meeting” is the place of purchase decision and agreement.

Was building a tech company something you dreamed about doing as a kid? If not, what was?

Not really. I didn’t play on my first computer until I was a teenager and although my best mates dad growing up was building arcade games in his garage I was more interested in the creative side of what business was all about, more than the cutting of code and software more generally.

I used to obsess over buying or starting a business. As a teenager I used to read the businesses for sale in the newspaper, which were mostly dairy’s and lunch bars and analyse the turnover and stock levels. Fortunately I didn’t end up buying a dairy as I would have grown to be fatter than I am.

Tell us a little bit more about your career journey and what inspired you to start PlayBooks?

This is startup number two for me. Before I kicked off startup number one I had a fairly traditional accounting career - albeit with some cool companies. I was the CFO of Nike Australia and the Group Financial Controller for Air New Zealand. I even did some time working outside of the business world (I ran a charity and one of the main political parties in NZ).

In 2006, I started my own business running a small accounting practice. By 2011 I was so bored. I met one of the co-founders of Xero and he and I and two other dudes decided we could build an accounting business that could scale globally. I was CEO. For six years I drove that business like mad. We (RightWay) went from the four of us to over 130 people becoming the largest accounting partner Xero had globally (i.e. we had more small business customers on Xero than any accounting firm in the world).

That put me on a speaking circuit internationally where I met accountants and discovered by accident they all had a problem - one that we also had. They had this trusted relationship with their small business clients but they didn’t know how to help them run a better business. For example if a Chef said “I have purchased a restaurant, but I do not know how to run one. I can cook and buy food, but how do I run a great restaurant?” their key advisor had no answer for them.

I realised that others did have the answers however. Someone knew how to manage rostering. Others knew how to do pricing, or set up a great point of sale system or alcohol licensing etc. But how could we get those people to help at the right time? I quickly realised the only way to do that was with software.

And that was the genesis of the idea that spawned into what is now PlayBooks.

Who have been your greatest role models and what have you learnt from them?

I have been fortunate to have some superb bosses over the years. My CEO at Nike was a great example. I was only 29 when I became the CFO for Nike Australia and he taught me so much. The imposter syndrome was alive and well for me when I took that role.

My Dad was also a great role model. Although he isn’t a business guy (he mostly drove trucks, sold trucks and managed trucking operations) he always taught me to believe in myself. His work ethic involved putting on a “high viz” vest and leaving the house early to go and work hard amid the dirt of construction and roading etc. I knew I didn’t want the dirt and the trucks. But I wanted to be one of the worlds best at what I did and to do what I loved. That was a lesson from Dad.

Where do you hope Playbooks will be in five years from now?

All going well we will be a multi-country operation with a dramatically larger team. Of course with high growth companies predicting how that will look and what we will be doing where is a phenomenally hard exercise. I believe our vision will take at least 10 year to bring to fruition and so given the exponential rate of how high growth works we will be about 20% of the way there (but half way from a time perspective).

How does Playbooks develop talent to be their best?

Hiring incredibly smart, talented folks, giving them what they need to excel and getting out of their damn way.

What does culture mean to you and how do you ensure this culture is maintained with everyone at the PlayBooks?

Culture is our most important secret sauce. Our people are everything. Without them we are nothing. Our culture is the glue that keeps them all together. We have a “radical candour” approach which means we treat people like we would if they were family.

We are 100% honest and 100% caring. We say it how it is, free of personal vilification or agendas. We just want to get shit done. That means being candid and free of hidden agendas. But done in a way that everyone knows we have each others backs regardless of what happens.

Lastly, as PlayBooks continues to evolve, what kind of talent do you want to hear from in the coming months?

Open minded to all possibilities.