Gary Steele is the CEO of Proofpoint, a company which is a leader in e-mail security, data loss prevention, and e-mail archiving solutions. Prior to joining Proofpoint, Gary served as the CEO of Portera, an applications company delivering solutions for the professional services industry. Prior to Portera, Gary was the vice president and general manager of the middleware and data warehousing product group at Sybase, Inc., an organization of more than 350 people spanning four regions and generating $150 million in revenue. Gary’s prior experience includes business development, marketing, and engineering roles at Sun Microsystems and Hewlett-Packard. He has a B.S. in computer science from Washington State University.
SM: Gary, let’s begin with a review of your background. Where are you from?
GS: I grew up in a small agricultural community of 600 people in the Northwest. It was a million miles away from technology. I got a computer science degree from Washington State and joined Hewlett-Packard, where I began my career as an engineer. I graduated in 1984. It was a very different time that was transitioning away from mainframes into the mini world.
I recognized that I loved science and math and thought that computer science would be a good way to use that intellectual capability. I was at HP for five years and spent over half of that time in engineering roles. I found that while I was not a bad engineer, I did not enjoy that role. I always wanted to get close to the customer. I constantly found myself doing things that were not related to my job.
I faced a big question early on. They wanted to promote me to run an engineering team when I was 22. I did not want to do that, so I took off to join the marketing team. I spent five years with that team, so I really feel that I grew up in marketing.
From there I went to Sun. I was there in the heydays of Sun and did a lot of different marketing and business development activities. From there I went on to Sybase as a VP/GM. I really loved running a business. That is what I got from that experience. I loved running that business, and I was involved in all of the early Internet products and features that Sybase was delivering at that time.
In 1997, I went off to run a very early SaaS company called Portera that was delivering application capabilities to the professional services industry. We raised more than $100 million in capital, primarily from Kleiner Perkins, IVP, and American Express. The business grew to $20 million in revenue before I sold the company in 2002. Having gone through the dot-com downturn, I recognized that I wanted to be in a role selling things people have to buy. I did not want to be selling anything that was optional.
My DNA was all about the enterprise and selling to companies. I happened to meet Eric Hahn, who was the founder of Proofpoint. Eric is a well-known entrepreneur and is very interesting with a phenomenal background. His observation at that time was that an opportunity to build a broad ecosystem around e-mail was emerging.
The first identified area where we believed we could build a product and win was helping people deal with all the security threats around e-mail. At that time it was becoming a much bigger issue.
SM: Was this all via a hosted architecture model?
GS: At that point it was not; we were just trying to solve the problem. I joined as the fifth employee. The Series A investors were Benchmark and Mohr Davidow. There was no money in the company because it had just been seeded.