Craig Bowman’s resume has a gap he couldn’t fill in for years. What reads as an early career in defense contracting was, in reality, a recruitment into the clandestine service.
That background — learning to map influence networks, reduce risk and move in zero-fail environments — turned out to be surprisingly good preparation for enterprise sales.
Now SVP of global public sector at Trellix, Bowman has spent his career arguing that the tradecraft of intelligence gathering and the work of building government technology partnerships aren’t so different. He wrote a book about it. He co-founded an organization after the Snowden leaks to help repair the fractured trust between government and the private sector.
In this Q&A, Bowman discusses how intelligence tradecraft shapes his approach to cybersecurity sales, why he sends his teams into the field rather than onto Zoom and what it actually takes to cut through the vendor noise in an AI-saturated market.
Can you provide a brief overview of your professional background and career progression?
On paper, my early resume says I started as a software engineer and technical lead for the Department of Defense. In reality, that DoD role was actually recruited into the clandestine service of the intelligence community. Following my time there, I built and sold my own government contracting firm, which eventually led to executive leadership roles at companies like Adobe, VMware, Verizon and now as a SVP at Trellix.
What landed me in my current role is a career-long focus on “mission-first” thinking. Whether you are gathering critical intelligence or leading teams that support government, healthcare, and education systems, you are fundamentally solving high-stakes human puzzles. My advantage has been knowing how to navigate those complex, zero-fail environments our partners operate in daily.
Why was this the path you chose, and how influential was it to your career?
I chose this path because I realized early on that the principles of elite intelligence gathering and building high-stakes partnerships are remarkably similar. In the intelligence community, asking someone to hand over classified information requires immense preparation, influence mapping, and risk reduction.
When I saw that those exact same tradecraft principles could be applied to solving complex problems across federal agencies, hospital systems, and university networks, it changed my entire approach. That realization became the foundation for my book, CRAFT, and it remains the operational engine for the teams I lead today.
Do you have a personal connection to the current mission you support?
To me, “the mission” is a very real thing—it’s the safety of our national digital infrastructure. Having served on the front lines of national security, I’ve seen the adversaries and the threats up close.
This isn’t just about pushing technology; it’s about arming frontline operators so patient care isn’t compromised, student data isn’t exposed, and critical infrastructure stays online. That passion is also why I co-founded the Redwood Project after the Snowden leaks. I saw that trust between the government and the private sector was fracturing, and I wanted to help build a unified, resilient cyber defense posture that protects everyone.
What are your current top priorities and responsibilities? How do these relate to your company’s overall mission/growth strategy?
My priority is scaling our cybersecurity solutions, but my actual responsibility as a leader is making sure my team gets deeply involved with our partners’ realities.
I don’t want my teams trapped on Zoom. I want them out there understanding the environment—whether that’s walking a sprawling university campus, navigating a clinical healthcare setting, or traveling to the southern border with CBP to see the physical and digital realities they face. You can’t align technology to a frontline mission if you don’t understand the ground it’s built on.
Where do you and your team see growth opportunities in your current field or portfolio you support, or what do you anticipate to be your customers’ top pain points?
The biggest growth opportunity right now is the AI inflection point. Organizations across the public sector, healthcare, and education are eager to move from reactive defense to proactive, predictive security.
However, the top pain point is tool fatigue and vendor noise. Our partners are managing incredibly complex environments with limited resources, and they are constantly pitched shiny AI technology by vendors who don’t understand their actual mission. If you can’t show exactly how your technology reduces the risk of systemic failure for their specific organization, the initiative won’t survive.
How are you and your team planning to address/prepare for these opportunities?
We address this by stepping away from traditional feature-pitching and executing tradecraft instead. We use the CRAFT framework: Conduct Research, Refine & Target, Activate, Find the Value, and Tailor & Validate.
Internally, I spend a lot of my time using AI agents as a personal “Chief of Staff” to automate deep mission research and map influence networks. We do this so our teams can lead with ideas that matter to the mission. When we meet with a partner, we don’t walk them through a 60-slide deck; we show up with a heavily researched hypothesis of value. We propose a solution that directly impacts their operational challenges, turning a standard vendor meeting into a highly productive working session.
How important is mentorship & networking in GovCon? Were they influential to your career?
In government, healthcare, and education, trust is the only currency that matters. True networking in this space isn’t about collecting business cards; it’s about understanding people. Often, the real power in a room sits with the clinical directors or the frontline operators who actually execute the mission, not just the executive at the head of the table.
Mentorship has been huge for me here. Leaders in the intelligence community and mentors like Ken Karsten and Barry Leffew taught me that people skills are a superpower and you don’t have to be the smartest person in the room. We actually ran an experiment once showing that simple “humility emails” sent by interns asking for guidance vastly outperformed the polished outreach of seasoned professionals that claimed to be in the “Leader Quadrant”.
What is something most people don’t know about you personally?
Most people who know my professional background don’t realize that halfway through writing CRAFT, I actually scrapped a significant portion of the manuscript. Right in the middle of the process, the AI revolution hit, and I realized it fundamentally changed the rules of elite engagement. Then, it happened again. Interns at Trellix proved that some of my hypotheses I outlined in the book were wrong; or rather ‘old’. I had to pivot the entire book to integrate AI and the lessons learned from students, still in college, as a core component of modern sales tradecraft.
Also, my entry into the intelligence community wasn’t exactly a standard interview process. It involved mysterious hotel lobbies, underground parking garages, and rooms filled with VCRs before I finally landed my first role. It was a bizarre experience, but it was the best training ground I could have asked for.