Rob has built a thriving founder-financed business from Toronto using very sophisticated strategic maneuvering. I just loved discussing the strategic nuances of this business. You’ll learn a LOT from reading this story.
Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?
Rob Douglas: I’m a Canadian. I was born just outside of Toronto. I have grown up in and around the city of Toronto. I’m married. I have two kids. Both of them are in their 20’s. I have spent most of my entrepreneurial life primarily focused on markets outside of Canada. US and EMEA have been primary markets over my career.
Sramana Mitra: Where did you do your education?
Rob Douglas: In Canada. I did a Business undergraduate course at McMaster University. I have attended the Queen’s University for the executive program partway through my career.
Sramana Mitra: What year did you come out of school?
Rob Douglas: I came out in 1985.
Sramana Mitra: What did you do after you graduated?
Rob Douglas: I managed to successfully complete a very long interview cycle. It took five months. I joined IBM.
Sramana Mitra: How long did you stay at IBM?
Rob Douglas: I was there for 10 years. I started in sales and moved into sales management and other management roles before I stepped down and left.
Sramana Mitra: What year did you finish your IBM career?
Rob Douglas: 1995.
Sramana Mitra: The Internet is already starting to become hot. What happens next in your journey?
Rob Douglas: I was in my ninth year at IBM when I attended a three-day career workshop. The deliverable of the workshop was to come up with a one-page summary of your motivational statement. On one page was a clear blueprint of who I am. That blueprint was what caused me to take every step of the journey I have taken since that time.
It caused me to leave IBM and to put all of my focus on learning from high-growth enterprise class software companies. I wanted to learn and participate with the best that Silicon Valley could offer. I joined Oracle. Oracle was getting into the software applications business, transitioning away from a database-only company. I wanted to go learn what it takes to scale enterprise-class software companies.
Sramana Mitra: How long was the Oracle stint?
Rob Douglas: I was at Oracle for about three years. I’m driven by hyper-growth. I’m driven by wanting to make a contribution to this world. The next step on that journey was I found on Gartner Magic Quadrant a new emerging market called salesforce automation. There’s a company called Siebel Systems. I joined them when it was a very young company. I participated in the hyper growth of Siebel over about a three and a half year period.
Sramana Mitra: What years were you at Siebel?
Rob Douglas: I joined Siebel in about 1998 and left in approximately 2001. At the end of the 1900’s, Siebel was written up by Harvard as the fastest-growing tech company in the history of technology.
Sramana Mitra: Siebel was a very successful company. At our weekly roundtable, we had Bruce Cleveland who was one of the earliest Siebel executives.
Rob Douglas: Yes, I know Bruce.