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The hardest part of security leadership isn't building better detection systems; it's staying connected enough to the daily work that you can still recognize when something doesn't make sense. William Glazier, Director of Engineering - Threat Research & Machine Learning at Cequence Security, refuses to detach from the operational reality his team faces. He's still in the on-call rotation, still debugging production issues, still analyzing customer data to understand how real investigations unfold.
William discusses why mental agility matters more than formal credentials when building security teams and how protecting space for people to follow their curiosity creates culture that outlasts any individual leader. He shares his framework for building trust through selective transparency about decision-making, why writing everything down during incidents prevents repeating the same mistakes, and how to recognize when you're letting emotions rather than data drive your responses.
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[33:30-33:56] “If you have a relationship with someone that's generally based on not being afraid to trade ideas and “Actually I disagree with you here. I disagree with this. What about this? What about that?” And then that stops. That's another red flag. And how do you build it? It's relying on you, again, having some North star that you've got to keep. People have to know some goal they're working towards, some broad vision.” 40:51-51:22
Speaker
William Glazier, Director of Engineering - Threat Research & Machine Learning, Cequence Security
William Glazier has built, scaled, and managed security operations while developing machine learning models for bot detection. His background includes everything from early threat intelligence work on residential proxy services to current challenges distinguishing good AI agents from malicious ones.
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Lindsay Kaye's career turned on a single decision: someone taught her reverse engineering despite her lack of experience, shaping her leadership philosophy around giving others similar opportunities. As VP of Threat Intelligence at HUMAN Security, she maintains hands-on technical work not as a compromise but as a strategic choice that builds credibility, prevents over-promising on timelines, and ensures she understands what her distributed team confronts daily tackling sophisticated ad fraud campaigns.
Lindsay also discusses her evolution from firm-deadline enforcement to empathy-driven management, her trust bucket framework that evaluates patterns rather than individual mistakes, and how she actively prevents hub-and-spoke isolation by encouraging peer-to-peer collaboration across six time zones.
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[17:12-17:22] “I think that making sure that they get to do work that they enjoy that benefits the company and then helping them understand how the things that they do actually benefit the company is really important.”
Speaker
Lindsay Kaye, VP of Threat Intelligence, HUMAN Security
Lindsay Kaye is an expert malware analyst and reverse engineer who loves taking on technical challenges of all kinds. She speaks regularly at international conferences such as REcon, Disobey, SEC-T, FIRST, and numerous BSides events. In addition to speaking, she leads training sessions and workshops that help others develop skills in the technical aspects of cybersecurity. Lindsay currently leads the Threat Intelligence team at HUMAN, building on her career from software engineer to reverse engineer to technical team leadership. A New York City native, Lindsay obtained her BS in Engineering from Olin College of Engineering before receiving her MBA from Babson College. She is also the author of Dissecting the Dark Web.
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The best security leaders don't pretend to know everything; they build teams where admitting knowledge gaps becomes a competitive advantage. Alex Cox, Lead of Artificial Intelligence Working Group at LastPass, has spent two decades proving that vulnerability creates stronger security organizations than technical heroics ever could. His approach to leadership, forged through military service and high-stakes security incidents, prioritizes trust and psychological safety over individual expertise.
Ben and Alex discuss how commander's intent from military planning translates to empowering security teams, why hiring for stress management capabilities matters more than technical credentials, and how AI is blurring the lines between individual contributor and management skills. Alex also shares his framework for spot feedback, his philosophy on when to lean on others' expertise, and why the transition from IC to manager remains one of the hardest career shifts in security.
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[14.47-15:07] “That's another favorite part of the job is to have a task and have one of my posts come back and go, “Hey, look at this!” And I'm like, “Man, I never thought of it that way. Or that's a really unique approach.” And showing it off to some of the other managers, seeing if you can apply the approaches in different places. That's a really fun part of managing a security team in general, because, like I said, it tends to produce people that think outside the box.”
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Patrick Gilman, Lawyer, Partner, & Co-Head of National Security Practice at Eversheds Sutherland, points to a disconnect between how professional services firms measure success and what actually drives sustainable team performance. Instead of P&L and billable hours, Patrick focuses on whether his team receives diverse, challenging work that develops broad problem-solving capabilities across multiple legal domains rather than creating narrow subject matter experts.
Patrick discusses the structural reasons lawyers fail at leadership. They transition from team member to team leader without formal training, law schools provide no leadership curriculum, and revenue pressure makes team development secondary to billing. He also explains his framework for difficult decisions through second- and third-order effects analysis, why he stopped reactive management behaviors after recognizing they produced no useful outcomes, and how he empowers junior associates to screen and approve hiring candidates before they join the team.
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[4:15-4:40] “But the difference between the two is lawyers, when they're operating, they're not brought up to operate a team. They're brought up to be a part, as a junior lawyer, to be part of a team. And as you grow through the ranks, you go from being a part of a team to leading a team without really understanding the transition and the roles and responsibilities of doing that.”
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Bryson Medlock's path to Threat Intelligence Evangelism Director, CW Research Unit at ConnectWise positioned him to address what actually creates high-performing security teams: treating people as individuals, maintaining psychological safety during crises, and building systems that eliminate months of manual work. Bryson shares how his leadership philosophy draws from a bit of nerdiness, including nearly two decades of running D&D campaigns where managing group dynamics requires constant attention to who's speaking and who needs encouragement to contribute. These frameworks translate directly into security team management, where recognizing that a fresh graduate needs hands-on guidance while a 15-year veteran needs autonomy and trust determines whether teams thrive or fracture.
The conversation explores how Bryson transformed ConnectWise's threat intelligence operations from months of manual spreadsheet work into automated systems that generate insights instantly. He also touches on conducting difficult conversations by focusing on observable facts rather than assumed intentions, building trust through recognizing individual needs rather than applying uniform management styles, and why panic accomplishes nothing in security operations where most situations aren't actually life-or-death.
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[13:44-13:58] “You have got to be able to know when to trust, and when to delegate. I think a lot of it comes down to just recognizing that what it means to be a human, everybody is an individual. Everybody's got individual needs and wants and desires”
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The biggest security failures don't happen because teams miss warning signs in the data; they happen because no one reported the warning signs in the first place. Jameson Ritter, Director of Behavioral Threat Assessment and Management at CPPS, discovered this truth after years responding to terrorism events and workplace violence as a law enforcement officer. His transition from the Joint Terrorism Task Force to corporate security revealed a consistent pattern: in nearly every tragedy, people knew something was wrong but never reported it. The gap wasn't in security infrastructure or threat assessment capabilities, it was in organizational culture and human behavior.
Jameson’s background also shaped his approach to building violence prevention programs that actually work. He discusses why 98% of effective prevention happens in the human sphere rather than through physical security measures, how to create multidisciplinary teams that leverage diverse perspectives, and why leaders need to embrace the "80% solution" when dealing with imperfect information about human behavior. He also explores the challenges of maintaining team mental health in a field that deals with tragedy and the importance of building trusted professional networks.
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[24:44-25:07] “I think they use the word passionate and that's not patting myself on the back, but I wear it on my sleeve. When I talked about the common thread line for me is this thread line of service. And now I've settled into this role of violence prevention and threat assessment. If you can speak authentically to things that you're passionate about and be knowledgeable on it, but also passionate, and that comes through in how you talk and engage with other people.”
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Kevin O’Connor's decade at the NSA taught him that the path to effective security leadership runs counter to most instincts: hire people smarter than yourself, let experts drive decisions in their domains, and focus on empowering careers beyond your team rather than confirming what you already believe. As Director of Threat Research at N-able, Kevin now applies this bottom-up approach to protecting small and medium businesses.
Ben and Kevin explore how mission-driven environments shape leadership styles that prioritize purpose over compensation, why mistakes become valuable only when you own the outcome and manage the recovery process, and how the transition from individual contributor to team leader represents the most challenging shift in any security career. Kevin also shares his framework for turning organizational roadblocks into opportunities, why project management skills separate effective leaders from those who struggle under competing priorities, and how to build team cultures where people actually want to spend time together beyond work obligations.
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[2:51-3:15] “And then I think also just being around that top talent, the people who were just so smart, I'm not the smartest guy in the room, but I'm pretty quick. But some of the guys I worked with, the guys and girls, they were just next level, next tier. And that always just drove me to make sure that I was never the smartest person in the room. That's the way you grow. If you're hiring to confirm what you're thinking or your mindset, you're never going to get anywhere.”
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The transition from individual contributor to manager destroys more promising security leaders than any technical challenge they'll face. Tom Cross, Head of Threat Research at GetReal, learned this while managing IBM's X-Force Research team, where his instinct to achieve goals directly conflicted with his responsibility to develop people until he harnessed that perspective.
Tom reflects on why vulnerability researchers need dedicated time for self-directed projects independent of business priorities, and how that balance creates environments where people give 120% because they're doing what they love. Tom and Ben also explore how Dunning-Kruger effects create friction between security teams and IT organizations, and how professional networks built over 25 years become almost everything about senior leadership opportunities.
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[37:58-38:27] “You end up in this management role, but you still have this goal orientation where you want to see the work get done and you have these people that you delegate the work to who may not be as good as you are at achieving those goals. And it's really hard to shift your mindset from focusing on achieving the goal to focusing on coaching the person that's there to the point where they achieve the goal.”
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The transition from technical excellence to leadership excellence often requires unlearning the habits that made you successful. T.J. Ramsey, Sr. Director of Threat Operations at Fortified Health Security, learned this lesson first in Iraq when incomplete analysis nearly endangered troops, then climbing from vulnerability analyst to director by mastering every service line he now oversees. His approach to building security teams reveals why some organizations maintain elite performance with lean resources while others struggle despite heavy investment.
T.J. discusses his framework for making rapid decisions under incomplete information, why he screens for personality traits before technical skills, and why the hardest career transition isn't learning new skills but learning when to stop using old ones. He also offers his approach to differentiating mentorship for CISO tracks versus business leadership paths, and why monthly one-on-ones with every team member reveal what annual reviews never will.
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[13:02-13:16] “They present themselves like a rock star, but when the rubber meets the road, they turn tail and run. Literally. It's incredibly disappointing. So I learned to really understand what it means to take a resume with a grain of salt.”
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Managing threat intelligence for 20,000 companies reveals patterns invisible to most security leaders. Alex Bovicelli, Senior Director of Threat Intelligence at Tokio Marine HCC, sees hundreds of ransomware events monthly, giving him a perspective that challenges industry assumptions about modern threats. The sophisticated attacks making headlines aren't what's devastating smaller organizations. It's groups like Akira Ransomware perfecting SSL VPN brute forcing over years, targeting predictable gaps in authentication controls.
Alex and Ben discuss how cyber insurance shifted from paper applications to technical risk assessment as ransomware as a service exploded, why Alex’s team focuses on native tools and simple configurations rather than threat feeds with obsolete IoCs, and what happens when you alert thousands of companies simultaneously about the same vulnerability. Alex shares his framework for extracting expertise from team members as you lose technical depth in leadership, and emphasizes that emotional intelligence matters more than maintaining hands-on skills.
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[32:39-33:15] I think it is critical for leadership to be very clear in the overall path of the program and the company so that those individual contributors can actually feel like they're participating in a strategic manner. I think the other thing that I find to be an issue that I've noticed is that as an industry we are expecting these kids to get out of school and just have 17 certifications, a master's in whatever, you know, and, we've actually lost touch with the fact that maybe, like, older generations, we understood it was a craft”
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