Sentry Technology Solutions

11/02/2026

A good IT partner brings the tools, the monitoring, and the expertise. What they can't do is decide who in your company should have access to payroll. They can't stop someone from approving a convincing fake invoice at 4:45 on a Friday.

The 2026 Verizon Data Breach Investigations Report found that 62% of breaches involved a human element, and third parties were involved in 48%.¹ Both numbers point to the same place: protection lives in the handoffs between people, policies, and partners.

So the better question isn't "Is our provider handling security?" It's "Do we know who owns what?"

Three ways to find out this week:
- Ask your provider for a written responsibility matrix: what they own, what you own, and what's shared
- Confirm who approves access changes when someone joins, changes roles, or leaves
- Check when your team last had security awareness training, and whether it stuck

In Sentry's Technology Maturity Model (TMM), this is the heart of the Secure stage. Clear ownership matters more than another tool.
Not sure where the lines are drawn in your business? Schedule a TMM audit today!

11/02/2026

How Retailers Vet PCI Security Providers Before the Holiday Rush

Retailers vet PCI security providers by checking their Attestation of Compliance, responsibility matrix, holiday coverage, and incident response plan.

10/22/2026

Phishing Drills: How to Run One That Actually Trains Your Team

A phishing drill should build reporting habits, not just catch clicks. Here's how to plan, run, and measure a simulation that changes behavior.

10/19/2026

Thursday night, a room full of Orlando business leaders got hacked.
Everyone survived. 🎃

Thank you to every owner, CEO, and leader who spent their evening at The Abbey working through a live breach with us. You asked the hard questions, made the tough calls at your tables, and proved that the best time to face a cyber nightmare is before it’s real.

A huge thank you to our co-hosts who made the night possible:

🛡️ Hylant, for bringing the cyber insurance perspective every leader needs before the 2 a.m. phone call
🤝 HR Soul, for reminding us that every incident is a people moment, too
💡 nPerspective, for helping turn a scary scenario into real, practical takeaways

To everyone who joined us: we hope you left with sharper answers, a few new questions for your leadership team, and some great new connections. If your table sparked a conversation you want to keep going, our door is always open.
See you next October. Bring your bravest face. 👻

10/14/2026

🚨 A few tickets are still available! 🚨
Tomorrow night, the breach happens in a room full of Orlando business leaders.

Cyber Nightmares is not a presentation. It is a live ransomware simulation where you sit at a table of 8 to 10 executives, a facilitator puts the incident in front of you one stage at a time, and your table has to make the calls. Who do you notify? Do you pay? What do you tell customers? Score is kept.

You will leave with a clear picture of how your business would hold up, and the questions worth asking your team on Friday morning.

A few seats remain. Thursday, October 15 · The Abbey, Orlando ·

Register here: https://bit.ly/4hDPbll

10/08/2026

Cybersecurity Awareness Month: A Field Guide for Business Leaders - Cybersecurity Awareness Month is a leadership moment. Use this four-week field guide to move your business forward one TMM stage at a time.

Cybersecurity Awareness Month is a leadership moment. Use this four-week field guide to move your business forward one TMM stage at a time.

10/05/2026

Selling in 2027? The IT Cleanup You Should Start Today

Planning to sell your business in 2027? Start your IT cleanup 12 to 18 months out: document systems, fix security gaps, and clean up contracts first.

10/02/2026

Your Team Is Already Using AI. Here's Why Shadow AI is a Leadership Problem

Your team is already using AI. Learn why shadow AI is a leadership and adoption problem first, and the steps leaders can take to turn it into an advantage.

10/01/2026

Cyber Nightmares 2026 — our live, tabletop cyber incident simulation for Central Florida business leaders — is coming to The Abbey on October 15. And we're proud to be sharing the room with three partners who are making this event happen.

nPerspective brings executive advisory expertise that helps business leaders think clearly about strategy under pressure. That's exactly what Cyber Nightmares puts to the test.

HR Soul understands the human side of a cyberattack — disrupted operations, exposed employee data, people looking to their leaders for answers. The decisions made in that room aren't just IT decisions. They're people decisions.

Hylant handles the other side of the equation: when the incident happens, what does financial recovery actually look like? What really happens with a cyber insurance policy? That's a question every business owner in the room will be thinking about. Hylant has the answers.

Together, we're giving business owners, CEOs, COOs, and directors a realistic look at what a cyberattack demands from them — before the real one arrives.

Seats are limited. Cybersecurity Awareness Month starts today. Don't wait.

👉 Register now: https://bit.ly/4ArnBza

📅 Thursday, October 15, 2026 📍 The Abbey | Orlando, FL

09/29/2026

On October 15, Sentry Technology Solutions is hosting Cyber Nightmares 2026 at The Abbey in Orlando — an immersive, hands-on event designed to put business leaders through a simulated cyber incident before the real one arrives.

This event is built for owners, CEOs, COOs, directors, and anyone who would be fielding calls when things go sideways.

Registration is open. Seats are limited.

If you've ever wondered how your business would actually hold up under a cyberattack, October 15 is how you find out.

👉 Reserve your spot: [Eventbrite link]

📅 Thursday, October 15, 2026 📍 The Abbey | Orlando, FL