Simon became MYOB’s CTO in January 2010. He is responsible for driving its digital vision in helping clients make the most of new technology. An IT practitioner with 15+ years of industry experience, Simon is well accustomed to working within innovating industries and specialises in bringing leading edge products to market. With a background in software engineering, Simon cut his teeth in Silicon Valley within a variety of companies across trading exchanges, e-commerce, business intelligence, communications, banking, and media and entertainment. His extensive systems architecture experience and business and product strategy knowledge make him highly qualified to bridge the gap between technology and business. Simon has a deep grasp of business owners’ needs and how technology can be used to meet these.

1.  What was your first job?

My first job out of uni was at one of the “Fast Five” consulting companies, Viant. It was set up in the late 90s in Silicon Valley to specifically service this new thing called the World Wide Web. That was the start of the Internet bubble and because things were moving so quickly I got to see and do so much in a very short amount of time. I think it was that experience that really gave my career a turbo charged start.

2.  Tell us about your journey. How did you get to where you are today?

I started life as a hands on developer, but very soon started taking on team lead roles. Over the next few years I started taking on more and more leadership and architect type positions and the teams I worked with got bigger and bigger. All the while I ensured I was still hands on as much as possible. The combination of leadership ability and technical skill I think has been the key to my journey.

Another factor was working in start ups. This is where I got to see many businesses spin up and grow up end-to-end multiple times, and in many diverse industries. Because startups are so small everyone has to do a bit of everything, which gave me the opportunity get to across a broad range of corporate and business functions.

3.  What does a typical day look like?

Every morning in the MYOB Melbourne office there are about 8-10 agile stand ups. Many are at the same time but I try to walk around and join as many as I can. This helps me keep abreast of the pulse of development that our 250+ developers are working on. This also helps me identify synergies across the various teams.

Then there are many meetings and other tasks I do on a regular basis. These range from various project steering committees, security council sittings, interviews, technology reviews, brown-bags, planning meetings, new project inceptions etc. Another important and enjoyable part of my day is the coffee run – seriously. I go twice a day, every day, and always drag a couple of people along with me. A surprising amount of innovation is born during these trips.

My own work begins later in the early evening when the office clears out!

4.  What is your biggest challenge when introducing Agile and new delivery concepts to an already established team and culture?

I approach all challenges of this type with the same three-prong parallel approach.

Prong 1: Do something small somewhere. Get a small team on a small project to simply jump into the deep end and start. Try it out, let people experiment and experience it, and observe it in action, but most importantly, start getting a feel for we are going to put own company spin on it. At MYOB we call this purplefication (because our logo is purple). Whatever you take on, you have to make it your own.

Prong 2: Deliver broad education across the organisation and raise awareness of the topic. As buzz starts to propagate natural curiosity takes over and whatever it is starts to build its own momentum. So do things like post articles on the Intranet, run brown-bags, watch videos on the topic in the lunch room, bring in external speakers, etc.

Prong 3: Educate senior management. You need to tailor the education process at this level to suit executives’ different styles of learning. This is true of any group. The same presentation on a topic like this (e.g., a brown bag) won’t get everyone’s buy in at that top level of the company. And that buy in is key.

5.  When you’re not working, you’re…

I have three little kids who keep me pretty busy but I also like surfing, volleyball and hanging at a cafe with my wife and the weekend newspapers. Building robots is also quite fun!

6.  Your advice to others who are starting out.

Go hard at everything you do. Every time you approach a situation think about how you can take it to the next level, how you can make it way better. Don’t let your thinking get stuck in a rut. At the end of the day think back over the decisions you made and judge yourself, be analytical about your own performance.

7.  How can others connect with you?

Twitter: @simonraikallen