HeyJaredCISO Tradecraft® Newsletter
Welcome to the CISO Tradecraft® newsletter, We believe that you are not years away from accomplishing your career goals, you are skills away. Learn the Cybersecurity Tradecraft to accomplish your career ambitions!
- Indexed issues, last 90 days
- 11
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- Sep 25, 2026
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- Jul 7, 2026
Latest issues
Why Your 2026 Security Training is Already Obsolete (opens the original)
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The Fatigue of the Familiar: Why We “Buzz Through”For anyone who has spent time in the orbit of the federal government, the imagery is burned into the collective consciousness: the same animated video, year after year, depicting the “dangers” of overseas travel. We all know the script, the same rental car at the airport, the same suspicious cardboard box tucked behind the rear wheel, and the same shadowy sedan tailing the protagonist to their hotel.As cybersecurity leaders, we see the result of
How to Create a Leadership Culture (opens the original)
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1. Introduction: The Invisible Force FieldIn the high-stakes world of cybersecurity, many organizations mistake “security theater”, the endless checklists, mandatory slide decks, and annual compliance box-checking, for actual security. But security isn’t a checklist; it’s a force field. And that force field is generated by your organizational culture.As a CISO, you cannot afford to be a passive observer of the environment you work in. You must be an intentional architect. While the tech stack ch
Why You’re Still Coding Like It’s 2022: Surprising Lessons from the AI DevOps Frontlines (opens the original)
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The era of hunting for missing semicolons and troubleshooting syntax for hours is not just fading, it is effectively dead. For decades, the software development paradigm was defined by manual labor: computer science majors pulling all-nighters to find a single misplaced colon. Today, that world has been replaced by “loop engineering” and autonomous tools like Claude Code.As we look toward the immediate 2026–2027 horizon, the cybersecurity DevOps landscape is undergoing a tectonic shift. Based on
Why Your CRM is a Better Security Tool Than Your Firewall (opens the original)
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1. The Enterprise Playbook is BrokenFor most small-to-medium business (SMB) leaders, the standard cybersecurity manual is a work of fiction. The “enterprise-grade” expectations, bloated frameworks, seven-figure hardware refreshes, and massive dedicated teams, simply do not scale down to a 50-person startup or a 13-person development boutique. When you try to force a mega-corp playbook onto a lean shop, you don’t just fail to secure the company; you alienate the very people you’re trying to prote
Why Your AI Strategy is Only as Good as Your Network Governance (opens the original)
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In the modern enterprise, developers can build and deploy a new application in a single afternoon. AI agents can modify infrastructure in a matter of seconds. Yet, in many organizations, opening the necessary network path for those applications still requires a manual ticket, three meetings, four approvals, and a specific engineer named “Bob” who happens to be on vacation.This is the “Bob on Vacation” Paradox: the chasm between the velocity of development and the sluggishness of traditional secu
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