Inside the hacker's mind: Where they'll strike in 2027
See through the attacker’s eyes and learn how to close the gaps they’ll go after next

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Session 1: How a hacker sees your business in 2027
Attackers go for the easiest way in, and it’s rarely where you’re looking. Jamie Woodruff and Dave Baggett show where attackers will look first next year, which everyday weaknesses they count on you to miss, and how faster, smarter tactics are changing what a break-in looks like. You’ll leave seeing your environment the way an attacker does.
Session 2: Close the gaps hackers find: Compliance that fixes itself
Only 27.6% of small businesses employ a dedicated IT compliance officer, yet leaders, auditors and cyber insurers want proof, not good intentions. Sam Duckett shows how Automated Endpoint Compliance Remediation, built into Datto RMM and Kaseya 365 Endpoint, flags drift as it happens, fixes affected Windows devices in bulk with technician approval, and verifies every fix on the next scan
What you’ll take away:
- The first doors attackers try in 2027, and the everyday weaknesses they count on you to leave open
- Which gaps to close first, once you see your environment through an attacker’s eyes
- Drift flagged the moment it happens, then fixed across every affected Windows device with one technician approval
- Proof on demand: every fix verified and logged for leaders, auditors and cyber insurers
Attackers are already planning their 2027. Join us to see what they see and leave with the plan to stay ahead of it. You can’t close a gap you never saw.