Heroes of IT – Sleeping Easier: Milton Webster’s Story of Risk Reduction with Automox, E18

Autonomous IT

In this episode of Heroes of IT, Ashley sit down with Milton Webster to explore how his team transformed their IT operations using Automox. From reducing endpoint risk scores in record time to implementing automated Windows 11 upgrades with Worklets, Milton shares real-world wins and challenges from the frontlines of IT. Learn how a culture of proactive patching helped his organization boost security and sleep easier at night. If you're navigating risk management, remote device updates, or end-user satisfaction, this conversation is packed with practical insight.

🔧 Topics Covered:
• Endpoint security & patch automation
• Risk score reduction with Rapid7 & Automox
• Worklet-powered upgrades & scripts
• Reboot strategies that actually work
• Culture change in IT and user communications

🎧 Whether you're an IT leader, sysadmin, or tech strategist, this episode delivers actionable advice from someone who's been there.