Cybersecurity risk is changing quickly, but many organizations are still trying to defend themselves using the same assumptions, habits, and checklists they have relied on for years.

Attackers do not think in checklists.

They look for weak access points, exposed systems, distracted employees, unclear processes, and small gaps that can turn into serious business disruption. For business leaders, IT teams, and decision-makers, one of the most useful ways to improve security is to step back and ask a different question: how would someone actually try to break in?

In this month’s PizzaCast, All In Technology will be joined by Jeff Hathcote, CISO and cybersecurity practitioner, for a practical discussion built around his Think Like a Bad Guy® program. Jeff will walk through how attackers evaluate organizations, where businesses are commonly exposed, and what leaders should understand as they plan cybersecurity priorities for 2026.

Jeff brings decades of experience across technology leadership, information security, infrastructure, risk management, and real-world threat awareness. This session will focus on practical insight, not scare tactics, helping attendees better understand how attackers think and how organizations can become harder targets.

What We’ll Cover

During this session, we will walk through both the strategic and practical considerations surrounding cybersecurity risk, including:

• Why cybersecurity risk looks different heading into 2026
• How attackers think when they evaluate a business
• Common gaps that make organizations easier to target
• Why identity, access, vulnerabilities, backups, and user behavior all matter
• How phishing, credential theft, ransomware, vendor risk, and network exposure continue to create business risk
• What leaders should be asking their IT and security teams before there is a problem
• How a Think Like a Bad Guy® mindset can help organizations make better cybersecurity decisions

This conversation will balance technical insight with practical guidance, making it useful for hands-on IT professionals as well as executive leaders responsible for operations, risk, compliance, finance, and business continuity.

Who Should Attend

This PizzaCast is ideal for:

• Business Owners and Executive Leaders
• IT Directors and IT Managers
• Security and Compliance Decision-Makers
• Operations and Finance Leaders
• Teams reviewing cybersecurity priorities for 2026
• Organizations concerned about ransomware, phishing, credential theft, vendor risk, or cyber insurance readiness

If your organization is trying to better understand cybersecurity exposure, improve internal awareness, or make smarter security decisions, this session will help provide a more grounded starting point.

Why This Topic Matters

A lot of cybersecurity messaging focuses on tools, alerts, and technical controls. Those things matter, but they only tell part of the story.

Real security improvement starts with understanding risk in context. What systems matter most? Where are users most exposed? Which vendors have access? Are backups tested? Are privileged accounts reviewed? Would your team know what to do if something suspicious happened?

The Think Like a Bad Guy® approach helps make those questions more practical. Instead of only asking what security tools are in place, this session looks at what an attacker would notice first. That shift can help leaders ask better questions, prioritize the right improvements, and build a stronger security posture heading into 2026.

June PizzaCast Event Details

Date: Thursday, June 18, 2026
Time: 11:30 AM MT / 12:30 PM CT
Location: Virtual Webinar via Microsoft Teams

This is a live, interactive session where you’ll gain practical insight into cybersecurity risk, attacker behavior, and the questions organizations should be asking as they prepare for 2026.

Qualified attendees who register by Tuesday, June 16th will receive complimentary pizza delivered for the session.

Registration will remain open after that date for webinar attendance, but pizza delivery closes two days prior.

Sign Up Below

Register for the June 2026 AIT PizzaCast below.