Blog by Shawn Skillman

Behind Every Software Update Is A Security Story
Insights Today for July 1st, 2026 - Hundreds of security fixes included in a recent Chrome update highlight the continuous effort required to protect modern software, reinforcing why routine updates remain an important cybersecurity habit for small businesses.
AI Growth Is Reshaping The Infrastructure Behind Business
Insights Today for June 29th, 2026 - A recent industry whitepaper suggests AI is increasing the importance of the digital infrastructure behind business, reminding small businesses that reliable connectivity and modern networks will play a growing role as AI adoption expands.
The Meaning We Bring To Compliance
Worth Noting for June 18th, 2026 - Compliance conversations can become confusing when frameworks, certifications, audits, and requirements start to blend together, but taking time to understand what is actually being asked can help small businesses avoid working toward the wrong outcome.
A Security Tool Is Not A Security Strategy
Insights Today for June 17th, 2026 - Recent attacks targeting accounting firms highlight how cybercriminals continue looking for ways around security controls, reinforcing the importance of multiple layers of protection rather than relying on a single tool.
AI Is Creating Dependencies Small Businesses May Not See
Insights Monthly for June 2026 looks at how AI features can create hidden dependencies across business tools, vendors, and information, and why understanding what those features rely on can help small businesses prepare for changes, outages, or loss of access.
Why Recovery Matters More Than Prosecution
Insights Today for June 11th, 2026 - A growing prosecution gap in cybercrime highlights why small businesses should focus on resilience and recovery rather than expecting criminals to be caught.
What Leaders Should Know Before Cyber Risk Becomes A Business Problem
Leader Guide | Cyber Risk - Cyber risk is often viewed as a technology issue, but its impact is usually felt through business operations, decision-making, communication, and disruption, making it important for small business leaders to understand how cyber risk becomes a business problem.
Recent Identity Report Highlights The Human Side Of Small Business Security
Insights Today for June 10th, 2026 - A recent identity report highlights how employee identity theft can extend beyond personal accounts and create exposure for the businesses where they work.
Ransomware Decisions Are Shaped Before Disruption Begins
Advisory Notice for June 8th, 2026 - Ransomware recovery can expose assumptions around systems, vendors, responsibilities, and business continuity before small businesses fully understand how disruption may affect daily operations.
The Hidden Risk Of Shared Platforms And Concentrated Data
Insights Today for June 4th, 2026 - A DentaQuest data breach affecting approximately 2.6 million accounts highlights how cyber exposure can extend through shared platforms, third-party vendors, and concentrated data environments.
Microsoft’s AI Agents Signal A Shift From Assistance To Action
Insights Today for June 3rd, 2026 - Microsoft’s expanding Copilot agent capabilities signal a shift from AI assistance to AI task execution, raising new questions about oversight, data access, approvals, and accountability for business leaders.
What Leaders Should Know Before Technology Projects Stall
Leader Guide | Project Readiness - Technology projects often lose momentum after implementation begins, making it important for small business leaders to establish ownership, communication, operational expectations, and follow-through before important work begins to drift.
Reading The 2026 Verizon DBIR Through A Small Business Lens
Advisory Notice for May 26th, 2026 - A small business interpretation of the 2026 Verizon DBIR, focusing on operational exposure, account protection, vendor dependence, employee awareness, and why security fundamentals continue to matter.
Cyber Insurance Is Becoming More Operational For Small Businesses
Advisory Notice for May 18th, 2026 - Cyber insurance conversations are increasingly becoming tied to operational readiness, security practices, response planning, and business preparedness as small businesses continue facing growing exposure to cyber and operational disruption.
What Leaders Should Know Before AI Becomes Everyday Work
Leader Guide | AI Awareness - AI tools are becoming part of everyday work in small businesses, making it important for leaders to understand where they are being used, what information may be involved, and how simple expectations can support responsible use.
The Digital Transformation Hiding In Plain Sight
Worth Noting for May 11th, 2026 - Small businesses may already have useful technology sitting inside the tools they use every day, but the greater opportunity is turning those overlooked features into everyday value through expertise, process, and follow-through.
Phishing Simulations Remain Important Despite Employee Fear And Distrust
Advisory Notice for May 10th, 2026 - Phishing simulations continue to play an important role in organizational security, though businesses are increasingly balancing employee readiness with concerns around fear, distrust, and punitive testing culture.
AI Voice Cloning Scams Are Expanding Into Business Fraud
Advisory Notice for May 9th, 2026 - AI voice cloning scams are becoming more convincing and more relevant to small businesses as fraud attempts increasingly target trust, communication, and verification.
A Bad Day For Your Tools Shouldn’t Stop Your Business
Insights Monthly for May 2026 looks at how ransomware downtime, customer data responsibility, and cloud tool disruption can affect daily operations, and why a simple backup plan can help small businesses keep customers served, information accessible, and the day moving.
Small Business Security Keeps Popping Up Everywhere
Insights Monthly for April 2026 looks at how phishing, cyber insurance, and software risk are showing up in everyday business decisions, and why clearer ownership can help small businesses know what to check, who should respond, what needs proof, and what to handle next.