Heroes of IT – Sleeping Easier: Milton Webster’s Story of Risk Reduction with Automox, E18
Download MP3In 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
• 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.
Creators and Guests

Host
Ashley Smith
Ashley Smith isn't just the voice behind the Heroes of IT podcast, she's a beacon for customer satisfaction and engagement. With her roots deeply planted in customer marketing, Ashley brings an unparalleled passion for nurturing strong, impactful relationships. At Automox, she ensures IT heroes are equipped, supported, and celebrated. Her episodes are treasure troves of insight, packed with real-world successes and solutions to the toughest challenges in IT. Ashley has a knack for getting IT practitioners to open up, making her interviews a gold mine for anyone wanting to grasp the intricacies of IT.
