What has motivated your biggest career transitions?

I got an opportunity to go to Uber and it was one of those weird instances where they didn’t really have a role for me, so I was just tasked with figuring out the managing of machines and then eventually grew into enterprise applications. That to me was the coolest part: managing all the bits and bobs that the customer would not see. What I really, really liked about Uber was the scale, the growth, creating a new market segment. I just really love consumer brands. But I decided to leave, because you get burned out because it's literally in your social feed, it's on the news, it's all just 24/7. When you’re at work and you really need to focus, there's so much noise. It literally burns you out because you can't get away from it. So it was definitely leaving the noise so to speak. I had to really make a deliberate decision because it is a big change to go from big company, big budget, everyone knows who you are to venture capital where you got a tiny team now, and budget isn't a thing. It was so different.

If you take the motivation for personal transition to a deeper level, the question is, “do you have purpose or do you have activities?” And I think with CIOs who have transitioned through many roles, it's safe to say we're purpose-driven. We're not here to do activities to pass the time and it was one of the reasons why I stepped away from the Splunk. It was just phenomenal. I mean, there's no question. It was a rocket ship while I was there. But, it is important to take time out to do a little bit of experimentation and see what catches your attention.

I actually took on techno management because within the organization there was a critical need for improving the way that people were working. So I decided to devote my life on improving processes, driving a cultural transformation, and working in a better way for my teams. That was what actually prompted me to go into management and then climb up the chain because I truly feel that people are the actual value streams within an organization. The more we invest in people rather than technology, the better every business transformation, digital transformation, whatever buzzword you want to call it, is going to be. I was very lucky to have driven the transformation for the company, brought multiple business units together and did all the interesting work that is necessary in order to become cloud-native.

Then I was asked if I would like to help Pivotal with their business transformations with our customers. I had never been in a customer facing role before, but the only way that one can grow is when they are in a level of discomfort. And so I was like, "Okay, this is something that I have never done before but probably I could." What actually got me going is understanding that the position is the same. You're just looking at it from a different perspective. You're still trying to improve the quality of life of people. The people that you're trying to improve are different now and you're trying to solve multiple problems of different customers rather than one single customer's problems. And the minute I started embracing that, I was like, "I've actually been doing it." I never acknowledged that I did it and so it wasn't such a hard switch. I also love to talk so that helps, but yeah, it wasn't that hard from a mindset perspective.

I don't think I thought about a career journey a whole lot until very late in my career, but I was making some more strategic moves throughout my career than I realized. It was always much more about the opportunity to learn, to build new teams, to just broaden my own personal portfolio in terms of what I did. And so I ended up doing two CIO roles in two pre-IPO companies but both were different. On the FireEye side, I continued to take on more responsibilities as I was there so it  was always new and different, evolving. Then when I went to Forescout, they wanted a CIO. I didn’t want to just be a CIO, I wanted to have an impact on the business. They were going through a transformation and I said, “Help me broaden the role into something else.” I took on the business operations function as well and that ultimately ended up taking on all of production operations and at some point ended up being the chief people officer. I think it's been more about a willingness to try new things, all with the common thread being leadership. Building teams and being able to lead (knowing what I don't know and getting other people to do that).

As a founder over the last 11 years I was very thankful for the opportunity I had to learn a lot about people's skills, company culture, and budget. It's a very different perspective, when you're looking at it from an owner/operator perspective because while you have your CIO, CTO, COO job, you're also responsible for everything else that's happening in the company. And so the exposure you have is awesome, you really get training in doing all things in the lifecycle of a company, but the challenge is your focus is split across multiple domains and you don't really get to do one thing well. As I looked at navigating myself and my career, I found that I wanted to focus on an area that I had a lot of passion for, which was cybersecurity. I wanted to do something where I could have a broad impact. And that's why I really zeroed in on this private equity industry where they help portfolio companies. Rather than just working for one company, you're working across multiple companies. I navigated through that change and zeroed in and said, "That's where I want to be."