Interview with Mr. Jackson Walker
Cybersecurity Architect for Valor Cybersecurity
November 18th, 2025
Interviewed by: Alexander Berrios
Since I began at Valor, I have worked almost exclusively with Jackson Walker. The CEO, Greg Tomchick, assigned Jackson as one of my primary points of contact for guidance and mentorship, in addition to himself. Jackson works virtually, so most of our conversations take place through Teams, phone calls, or text messages; however, despite never meeting him face-to-face, his mentorship has already left a lasting impression on me. I’ve chosen to interview him because he’s an intelligent, personable, and engaging colleague who leaves me inspired and motivated after each conversation we share. He displays wisdom well beyond his years, and I consider myself fortunate to work alongside him.
Entry Into Cybersecurity
A large theme throughout the interview was Jackson’s intentional journey into cybersecurity. His early interest in computers began in middle school, where he taught himself how to build PCs by watching YouTube videos and experimenting with hardware. This ultimately led him to study computer science at Christopher Newport University (CNU), where he later discovered that a new cybersecurity major was being offered. Noting the similarities between both programs, he chose to pursue a double major during his junior year.
While pursuing his double major, he managed to continue working in software engineering during his internship with NASA. He admitted that he lacked networking knowledge and broader technical theory exposure, however, studying cybersecurity helped fill that gap. He also noted that his computer science background has given him a competitive edge during his search for cybersecurity opportunities.
Reflections
When asked if he would have done anything differently entering cybersecurity, Jackson expressed overall satisfaction with his path. He believes that his foundation in programming, operating systems, and fundamental computing made advanced security coursework significantly easier. His advice to individuals entering the field was to master the “hard, technical skills first,” as these skills later develop into problem-solving abilities and provide fundamental expertise that remains valuable throughout a career.
He added that if he were to change anything, he would have pursued additional certifications earlier, specifically cloud or beginner penetration testing certifications.
Skill Development
Jackson emphasized the difficulty of time management and learning to work effectively under strict time constraints. In a professional environment, ensuring productivity within defined timeframes is essential, especially while attempting to maintain a healthy work-life balance. He explained that “anyone can get something done if they work 40 or 50 hours,” but learning to achieve the same levels of productivity in 20 hours is a challenge. Developing this efficiency was one of the most difficult skills he has been continuously learning to improve.
He also highlighted the importance of mastering the fundamentals: networking concepts and core computing knowledge that “hasn’t changed since the 70s.” He stated that these foundations are timeless and remain relevant no matter how the field evolves.
Roles, Responsibilities, & Growing at Valor
Jackson’s role at Valor shifted slightly after another team member, Derek, left the company soon after I onboarded. Initially, Jackson shared client responsibilities and shadowed Mr. Tomchick, Valor Cybersecurity CEO, learning about operations and the business model. With time, Jackson took on tasks and additional responsibilities such as:
- Leading client calls
- Developing CMMC documentation (SSPs, WISPs, IRPs)
- Building internal processes
- Managing all clients previously handled by Derek
The turnover with Derek doubled his workload, giving him ownership of 8 clients overnight. This transition demonstrated Jackson’s adaptability, organizational discipline, and enhanced understanding of Valor’s operations and services.
At Valor, the most challenging skill Jackson described as needing to develop was maintaining organizational discipline: keeping track of every client, their documentation status, and their unique CMMC needs. Without a standardized tracking system, the Valor team builds some internal processes “on the go,” making organization, collaboration, and communication critical.
He manages these challenges through note-taking, organizing emails into client-specific folders, and utilizing LLM scripts to automate and speed up repetitive tasks. His inclination towards standardization and maximizing efficiency helps him balance his various roles and responsibilities smoothly.
Technical Skills & Daily Tools
Jackson leans heavily on this strong programming experience working at Valor, noting that he uses personally customized scripts and artificial intelligence (AI) to streamline tasks. When dealing with high-volume work, such as preparing multiple WISP documents, he utilizes scripts in conjunction with LLMs to analyze documents, extract and organize specific sections, and identify discrepancies. His utilization of AI as a tool to assist with completing the work, rather than relying on it entirely to complete the work, reflects a uniquely intentional approach that enhances his efficiency while ensuring he maintains full control over the quality and accuracy of all his products.
He also uses tools like Mermaid, a script-based diagramming program, to generate visual flowcharts for clients during meetings. These visual aids help bridge the gap between technical concepts and clients who may not entirely understand. These diagrams proved especially useful in simply explaining how Controlled Unclassified Information (CUI) moves through an organization.
Present & Future Skills
Jackson emphasized the need for constant learning within the cybersecurity field. He’s determined to continue improving his core technical expertise, with cloud certifications being his priority. He expressed interest specifically in the AWS Cloud Practitioner certification to complement his Microsoft Azure experience. He’s also considering certifications related to CMMC auditing. Overall, Jackson makes it clear that he values technical skill growth significantly more, since many soft skills come naturally to him.
New Hires & Measuring Performance
Jackson highlighted two main qualities he looks for when evaluating new hires:
- Self-Starters – Being able to take ownership of tasks and solve problems without handholding.
- Personability & Professionalism – Especially important when communicating with CEOs and business leadership
While technical knowledge matters, he emphasized that those skills can be taught, while initiative and professionalism cannot. Valor is a small business without formal evaluations established to measure performance; in place of this, Jackson believes employee performance should be measured directly by how they support CMMC documentation, client readiness, and mutual endeavors.
Career Aspirations
Looking ahead, Jackson sees himself continuing to help Valor grow, gaining deeper experience with running small business operations. Eventually, he would like to start his own company or work in more advanced infrastructure or low-level engineering positions. Ultimately, he aspires to “build things and have a big impact”, regardless of where his career leads.
Conclusion
The interview with Jackson reveals a cybersecurity professional who blends technical expertise, self-driven initiative, and commitment to continuous learning. Reflecting on his journey, he reiterates the value of developing foundational skills in cybersecurity and encourages embracing unconventional career paths. His insights from our conversation provided meaningful guidance for aspiring cybersecurity professionals at any stage of their career. Echoing the words of the book he recommends to anyone navigating their career: “Be so good they can’t ignore you.”