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From Excel to Excellence: Transforming Cybersecurity Workforce Management | A Brand Story with Deidre Diamond, Founder and CEO of CyberSN, and Carraig Stanwyck, CEO and Former Fortune 200 CISO | A Black Hat USA 2025 Conference On Location Brand Story
Episode 2474
Marco Ciappelli of ITSPmagazine explores cybersecurity workforce transformation with CyberSN's Deidre Diamond and Fortune 200 CISO-turned-CEO Carraig Stanwyck
The corridors of Black Hat 2025 in Las Vegas buzzed with conversations about AI and emerging threats, but one of the most compelling discussions centered on something decidedly human: how we actually manage our cybersecurity teams. Marco Ciappelli, Co-Founder and CMO of ITSPmagazine, connected with longtime industry colleague Deidre Diamond, who brought along Carraig Stanwyck—a seasoned cybersecurity leader who recently transitioned from Fortune 200 CISO to CEO.
"It's been great running into people I know here at Black Hat," Ciappelli noted, "but finding Deidre after 11 years—and meeting the people she's been working with—that's what these events are really about. Finding out what's happening in the industry and reconnecting."
Diamond, who has spent 11 years in cybersecurity with eight years focused on talent matching and three years developing workforce risk management practices at CyberSN, brought a unique perspective to the conversation. Her journey from building a cyber taxonomy and job matching solution to addressing the industry's critical workforce challenges—retention, burnout, capability gaps, and career planning—set the stage for understanding how one Fortune 200 CISO discovered the limitations of traditional workforce management.
The Excel Trap: When Good Intentions Meet Reality
When Stanwyck thought he had workforce management figured out, he was using Excel spreadsheets and conducting regular happiness surveys with his cybersecurity team. As someone who started his career in human intelligence and carried that people-focused approach through government, startups, and enterprise organizations, he believed he was ahead of the curve.
"I thought I already had a solution," Stanwyck reflects. "I was already meeting with my people, doing specific surveys to track happiness and belonging because I wanted to catch issues early. You get your team right, and you can do anything."
But when he met Deidre Diamond from CyberSN at RSA two years ago, his confidence was quickly shaken. "She was talking about workforce risk management, and I was like, 'Well, yeah, I do that. I'm all set. I'm covered.'" Diamond's response was simple: "Show me how you visualize the data you use."
That's when Stanwyck discovered the limitations of his Excel-based approach—old data, time-intensive processes, and a fundamental lack of real-time visibility into how his team actually functioned.
Beyond Job Titles: The Hidden Workforce Reality
What CyberSN's platform revealed transformed Stanwyck's understanding of his own team. "You can re-interview your people like a recorder," he explains. "You can see that someone you hired as an analyst is doing all this engineering work—maybe they're better on the engineering team."
The platform provided something Stanwyck had never experienced: quantitative visibility into how his team's time was actually being spent. "It gave me a level of visibility in the team, what they were doing, and how their time was being spent at a quantitative level that there's no way for me to replicate manually."
Even more revealing was the discovery that job descriptions become obsolete almost immediately. "The job description of our talent is old within weeks and within months from the day it's created—if it was even created correctly at all," Diamond noted during the conversation.
The Fulfillment Factor: Beyond Happiness to Purpose
While Stanwyck's happiness surveys captured surface-level satisfaction, CyberSN's approach dug into something more fundamental. "HappinessHappy is important, but one that feels fulfilled—that they have a purpose—that's the key," Stanwyck emphasizes.
The platform's approach to understanding team members went beyond traditional metrics. "When you know wh
Published on 4 months ago