CIO Leadership Advice: Lessons from Sales and Go-to-Market with Julie Cullivan, Former Forescout CIO

Julie Cullivan on Becoming a First-Time CIO, Why Sales Experience Makes Better Leaders, and What Working with Startups Is Really About

Julie Cullivan, Board Director, Axon / HeartFlow / AaDya (former CIO, FireEye; former CTPO, Forescout) | Interviewed by Luke Alie of Atolio

Julie Cullivan spent the first part of her career in corporate finance and go-to-market roles at companies like Autodesk and McAfee before Dave DeWalt recruited her to become the first CIO at FireEye, telling her she had everything it took despite never having been an IT person. She later became Chief Technology and People Officer at Forescout, one of the more unusual executive titles in the industry. She talks about what the pivot taught her, what sales experience gives you as a leader, and how she thinks about building honest relationships with startups.

A Larger-Than-Life Character and a Phone Call That Changed Everything

Luke Alie (LA):  You made a pivot from go-to-market into becoming a first-time CIO at FireEye. Can you tell me about that?

Julie Cullivan (JC):  I had spent 15 years on the go-to-market side after starting in corporate finance. When Dave DeWalt became CEO at FireEye, he was building out the executive team as part of a plan to take the company public quickly. He approached me about a role, and I assumed it would be something go-to-market related. Instead he said: I want you to be the first CIO at FireEye and also own the security function, which was critical for a security company that was also a target by bad actors.

My first reaction was: you have the wrong person. But as we talked it through, his argument was essentially: you understand the business inside and out, you build great teams, you get things done. You have everything that makes someone capable of making this shift. And he was right that the downside was limited: the worst that could happen was that it wasn't for me. I'm so glad I made that move. It gave me a completely different outlook, a whole new function, and I learned enormously from stepping into something I had not grown up through.

What Sales Experience Gives You as a Leader

LA:  When you were adapting to the CIO role, what from your sales background helped you?

JC:  Everything ultimately comes back to the customer. Whatever function you are running, that's the reminder of why you do what you do. Even the fire drills, the understaffing, the tight deadlines. If you re-anchor on: this cloud transformation is critical because of what it means for the customer, it re-energizes people. It shifts the framing from endurance to purpose.

And I think we are all salespeople. Whatever you do, you are selling every day. Being in an actual sales role, even briefly, teaches you so much. How to pitch. How customers want to buy. How to ask hard questions. How to collaborate. Those skills transfer into every role you'll ever hold after that.

Being CTPO: What the Unusual Title Taught Her About Leading People

LA:  As CTPO at Forescout you owned both technology and HR. What did that combination teach you that more typical CIOs might benefit from?

JC:  Do not underestimate leadership, communication, empathy, and the ability to personalize your interactions. What is sometimes seen as soft in a technology context is actually what's most critical.

I was not a career IT person who became CIO. I stepped into it. What helped me make that transition wasn't knowing every detail of the network architecture. It was knowing how to lead, how to make risk decisions, and how to build trust with the team. I always made sure they knew I had their back. When things went well, they got the credit. When things didn't, I took the accountability. Building that understanding is what creates sustainable teams.

And don't think that because you have a C in your title you don't need to know the people. One of the first things I do at any leadership role is skip levels throughout the organization. New hires: 30, 60, 90 days in, I get them on my calendar. How's it going? So many people have come to me and said they never had a one-on-one with their previous CIO in their entire career. What made those people think they were too special for that? You don't build trust with a team at scale by staying in your office.

Working with Startups: Design Partners, Honest Feedback, and the Long Game

LA:  What has your experience working with startups been like?

JC:  Particularly in the security space, there is so much innovation happening that you can't afford not to be engaged with it. My approach has always been: I'm willing to engage, but it has to be in the context of initiatives already on the radar. And you have to be honest on both sides about what is reasonable effort.

The most important thing a startup can do is be specific about what they do and don't do. When someone says very clearly: this is what we do well and this is what we don't do, that is far more useful to me as a buyer than overselling. I can take that honest picture back to my team and have a productive conversation about whether we want to invest the time. My goal is never just to check a box. I want something that genuinely matters to the organization, not just to me. And I want my team to learn and get excited along the way.

A Success Story: Growing with Cobalt.io from Four Founders to Market Leader

LA:  Can you share an example of a successful startup relationship?

JC:  My best story is Cobalt.io, which I first engaged with through the Stanford Accelerator when they were four founders going after a different problem entirely. They did a pivot and became the leader in pentest as a service, growing from four founders to 150-plus employees.

I was with them on the journey from the beginning, long before I was a customer. I was able to contribute from a buyer perspective, from a scaling perspective, from many different angles. And I learned a lot from them too: I had never worked for a four-person organization. Seeing that part of the journey was invaluable. I eventually became a customer when they filled a genuine need. That's the ideal arc: you start off on the right foot early, and whether that leads to becoming a customer today or two years from now, the relationship is what matters.

LA:  Julie, thank you so much for coming on the show.

JC:  Thank you. My pleasure.