In this week’s episode of The Future of Security Operations podcast, I'm joined by Joe McCallister. Joe’s journey in security is truly unique - in less than a decade, he pivoted from selling BMWs to his current role as Senior Manager of Cybersecurity Operations at The Trade Desk. He’s also led impactful initiatives in risk management, threat hunting, and incident response at Synoptek.
In this episode, Joe and I discuss:
What it’s like to pivot from selling BMWs to leading a security team at a global company
How to navigate salary conversations as both a manager and a practitioner
Balancing technical priorities with broader business goals
Learning to let go and trust in your teammates
Strategies for internal networking and stakeholder alignment
The fine line between being a hands-on leader and a helicopter manager
How AI looks set to reshape the future of SecOps
Identity, MFA, and the evolving authentication landscape
Managing imposter syndrome while growing as a security leader
Where to find Joe:
Where to find Thomas Kinsella:
Resources mentioned:
In this episode:
[02:18] Transitioning from selling BMWs to leading a security team
[06:14] Moving from practitioner to manager and leaning into the role of the "communications guy"
[09:52] Balancing security team priorities with company goals
[11:40] The threats that keep Joe up at night
[14:06] How The Trade Desk's rapid growth has affected day-to-day operations
[16:10] Ensuring security stays top of mind for other business units
[19:32] Practical tips for strengthening collaboration with IT and other teams
[22:13] Joe’s approach to hiring and building a resilient team
[26:30] Enabling his incident response team to thrive, even when he's not there
[30:58] Joe’s top three leadership principles
[33:22] Tips for salary negotiation, both as a practitioner and a manager
[39:58] Navigating imposter syndrome and anxiety
[42:37] How AI is fueling Joe’s optimism for the future of SecOps
[44:29] Connect with Joe
TL;DL? Read Joe’s take on:
What excites him most about the future of SecOps
“If there was no better example of the thrill of technology and security in general, just look at what's happened in the last two years with AI. I think it’s such an interesting new world. Everybody's interested in it, and then they come to you and say, ‘Wait a minute, have we thought about security?’ Which is maybe the first time I've ever seen a technological leap like this - where they're also asking about the security of models, the training data.”
AI has really kind of juiced my optimism for security and technology in general. People are excited about it. Now, we're starting to see some real energy in the space, and it's really fun to watch.
Imposter syndrome
“I absolutely do experience it. I recently had a very candid conversation with one of my leads in a one-on-one. I told her I suffer from anxiety, and she was like, ‘No way, I did not picture that. You seem like an extrovert.’ And I was like, ‘Yeah, I am, until I'm not.’ I've been at conferences where, by day two, I'm like, I'm going back to the hotel room - 'Do not call me, do not text me. I am done.' I think everybody fights these things that we’re not aware of whatsoever. Some people do a great job of putting on the mask.”
It was a very strange moment when I was able to say, ‘...People want to know what I think about this new initiative, this risk assessment, or this new technology.’ When people come to you and ask you a question, they're there for a reason - it's because you know your stuff.
Winning over stakeholders and colleagues
“The easiest way is probably going to be really informal - just take somebody out to lunch. Go for a walk. Ask them, ‘Hey, what's on your mind? What are you trying to get done in 2025? What projects excite you? What’s the status on those?’ Because you can really serve as an unblocker.”
Really understand where you want to go. A lot of people don't know the doors that are presented to them once they get through. Network a ton, as best you can. Talk to somebody on your team at a different office or something, just to get a different perspective.
His top three leadership principles - assuming positive intent, recognition, candor
“They’ve served me so well. I’ve always received a better boon from building strong relationships and assuming positive intent. Rarely have I found anybody was actively trying to do something malicious, or avoid doing something. I don't think that’s truly what most of us are trying to do in our day-to-day jobs. What helped me was being able to sit down with somebody and understand what they're trying to do. Our goals are the same. It’s not you versus me - it's you and me versus the problem. So let's find a way through.”
Understanding is what gets everybody moving forward. And how I got there was just trial and error. I can try and kick in doors, but it has never worked in the long term. The tenure of people who do that is usually pretty limited.
Navigating salary conversations: tips for practitioners
“There’s no harm in negotiating upfront, especially if you've built the rapport through the interview process. And if you've really understood what the company needs, you can transparently discuss what your needs are, as an individual and a contributor to the organization. You might say something like, 'Here's the value I can bring to you. I believe we can reach an agreement. I appreciate your initial offer. Is there any room for discussion here? Could we take a closer look at the numbers?'"
It’s drastically important to value yourself and understand what your worth is. Be realistic, too. I think there are two extremes - we either way overvalue, or way undervalue. I found myself undervaluing myself for a long time, and I think a lot of that comes from imposter syndrome.
Navigating salary conversations: tips for managers
“I try to share a little bit of the math. I can't peel back the entire curtain, because I am not the payroll team, nor am I an accountant, nor am I even good at math in the first place. My job, honestly, is very easy when conveying the value the organization reflects to its people. We have an amazing package. So I try to explain the levers that we have at our disposal, which are base salary and equity. It’s not an option at every company, but it's worth knowing if it is an option.”
You should be able to answer this question for all your direct reports, and their direct reports: ‘What do I need to do to get to the next level?’ As you grow and scale, you need to look at them every year.
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