John Stewart, SVP, Chief Security and Trust Officer for Cisco, recently announced that he is leaving his role. What's next for him and his career? 

Security magazine: We spoke in 2014 about the cybersecurity talent gap, and you said at the time, “This will be a 4 to 8 year cycle” to close the gap. How is the industry doing since you made that statement?

Stewart: Looking back, my estimate was wrong – it will take 25 percent more time than I thought. I continue to see higher demand for talent, although I’m encouraged by many factors. The number of community colleges and universities that started cyber programs is significant globally and are now graduating classes, and the open job growth appears to be slowing gradually. I’m also encouraged to see pilot programs on micro-training, and that SANS continues its success and growth in training. A missing area? Software security – this needs to be brought into computer science and cybersecurity programs.

Security magazine: You just announced that you are leaving Cisco to focus on being an investor, advisor and board member. What led you to that decision?

Stewart: My overarching career strategy combined with three specific factors. First, I have a career strategy – which I didn’t until I was 35 and an individual taught me an important life lesson which is to manage my career. I just had to laugh that I wasn’t really managing it, and then created a strategy for myself.  Now add the three factors, as I told my team when it was announced, one selfish and two unselfish. The selfish was one is my desire to focus on other passions: disruptive startups including Code Dx, the winery that I’ve invested in, and giving back – mostly likely in the form of helping anti-poaching efforts in Africa. The unselfish factors are 1) Cisco and my team are in a great place and my big goals in going to Cisco are largely underway and succeeding, and 2) after 17 years building this team, I think it is incredibly important to have new thinking so I don’t become the problem!

Security magazine: How did you get interested in IT security?

Stewart: The movie War Games, the Robert Morris, Jr. Internet worm, the book The Cuckoo’s Egg, and work I was doing at Syracuse University as a student in securing the University when a couple of people from the Netherlands were hacking in. It fascinated me, and I was lucky to meet pioneers in this such as Michele Guel, Alan Paller, Tom Christiansen, Wietse Venema, Dan Farmer, Rob Kolstad, etc. I’ve loved working in the field even before it was one.

Security magazine: What work are you most proud of with your former role at Cisco?

Stewart: Making a difference, and doing so in a way that benefited customers, shareholders, and employees at the same time. Cisco now has the world’s most effective security portfolio with world-class researchers fighting the fight; we have industry leading security and privacy teams protecting the business each and every day, we have graduated CSOs, CPOs, and entrepreneurs alike into industry while operating Cisco’s most successful intern and early in career practice, and we took care of one another – both internally during good and bad times, and externally with teams like TACOPS. And that doesn’t talk about the changes Cisco went through along the way, and the multiple CxO roles filled with different people over these past 17 years.

Security magazine: What do you like to do in your free time?

Stewart: My free time is filled with family, friends, focusing on my health, reading, and photography. I’m an eternal learner and am driven deeply to make an impact, and all of those teach me, humble me, and make me strive to be better, and allow me to make a difference here and there. I am incredibly lucky, and I try very hard to remind myself of that each and every day.