Charles Henderson, who leads the cybersecurity services division at Coalfire, shares how the company is reimagining offensive and defensive operations through a programmatic lens that prioritizes outcomes over checkboxes. His team, made up of practitioners with deep experience and creative drive, brings offensive testing and exposure management together with defensive services and managed offerings to address full-spectrum cybersecurity needs. The focus isn’t on commoditized services—it’s on what actually makes a difference.
At the heart of the conversation is the idea that cybersecurity is a team sport. Henderson draws parallels between the improvisation of music and the tactics of both attackers and defenders. Both require rhythm, creativity, and cohesion. The myth of the lone hero doesn’t hold up anymore—effective cybersecurity programs are driven by collaboration across specialties and by combining services in ways that amplify their value.
Coalfire’s evolution reflects this shift. It’s not just about running a penetration test or red team operation in isolation. It’s about integrating those efforts into a broader mission-focused program, tailored to real threats and measured against what matters most. Henderson emphasizes that CISOs are no longer content with piecemeal assessments; they’re seeking simplified, strategic programs with measurable outcomes.
The conversation also touches on the importance of storytelling in cybersecurity reporting. Henderson underscores the need for findings to be communicated in ways that resonate with technical teams, security leaders, and the board. It’s about enabling CISOs to own the narrative, armed with context, clarity, and confidence.
Henderson’s reflections on the early days of hacker culture—when gatherings like HoCon and early Def Cons were more about curiosity and camaraderie than business—bring a human dimension to the discussion. That same passion still fuels many practitioners today, and Coalfire is committed to nurturing it through talent development and internships, helping the next generation find their voice, their challenge, and yes, even their hacker handle.
This episode offers a look at how to build programs, teams, and mindsets that are ready to lead—not follow—on the cybersecurity front.
Learn more about Coalfire: https://itspm.ag/coalfire-yj4w
Guest: Charles Henderson, Executive Vice President of Cyber Security Services, Coalfire | https://www.linkedin.com/in/angustx/
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