I left and went back to Fidelity for three years, back in Boston, and shifted to enterprise architecture and application security. I realized that firewalls weren't going to meet the needs of the future. I got involved in application security and that led me to identity security, which was what I believed would become foundational to securing services at scale. That got me involved in the Liberty Alliance and I was Fidelity's representative there. I was also doing due diligence for Fidelity's Venture Capital team and looking at companies to invest in. That led me to meet the founder of Ping Identity, Andre Durand, and I left Fidelity to become CTO of Ping.
2. Who was an influential boss for you and what lessons did they teach you about management and leadership?
One of the most influential was the boss I had at Fidelity, a guy called Steve MacLellan.
I would describe my management style and leadership as low touch. I expect the people I hire to be exceptional at what they do, to be able to go off and do the things they do with minimal direction, be self-directed and as such to really only need to come back and interact with me when they have reached a road block. That's the way I was managed. It relies on trust, but allows for a lot of opportunity to be creative and think outside the box while not being micromanaged. You didn't have to report on every single thing you were doing. You can be empowered and are trusted to go off and do the right thing.
I didn't necessarily realize it when it was happening but that meant I had a level of freedom and empowerment that allowed me to go off and do a lot of things. For example I saw that Fidelity had a remote access problem, so I effectively built and deployed at Fidelity an SSL VPN before they existed. They wound up replacing it with a commercial SSL VPN a few years later, but that level of innovation and allowing it to occur was a real important revelation for me.
I encourage my team to go off and innovate within certain guardrails. The team I have includes both the CTO office as well as the Ping Labs team, so it's meant to be a set of freethinkers who need to be able to think strategically about where we're going.
3. What are the biggest challenges facing CTOs today?
Honestly, it's just the rapid pace of change. The rate of change in technology and innovation only seems to accelerate and has been accelerating the last 20 years. Staying on top of that without necessarily being able to go as deep into it as you could if you chose to specialize is challenging. It just is. It's hard to keep up and understand this stuff at the level of detail you need to make good decisions. You've got to rely on other people to be able to help you make those decisions.
Keeping up with that pace of change is incredibly challenging and difficult.
4. What is a good day at work like for you?