
← The Disciplined Troublemakers6 May 2025 · 48 min
Turning Cybersecurity Compliance into a Catalyst with Jason Young
Welcome to the Disciplined Troublemakers podcast. In today’s episode, we speak with Jason Young, founder and CEO of Pylon Cybersecurity. Jason Young is the founder and CEO of Pylon Cybersecurity, a firm he started in 2011. Pylon helps security managers automate network compliance through real-time services which ensures data accuracy and a definitive chain of custody.
In 2024 Jason and the team saved the Defense Health Agency, a Combat Support Agency w/in the U.S. DoD that supports medical services readiness for the Army, Navy, and Air Force, $25 million dollars by optimizing their cyber compliance workflows.
Chapters:
00:00 - Introduction
00:09 - Scaling Cybersecurity with Jason Young
03:48 - "From Systems Admin to Auditor"
08:01 - Cybersecurity: Cost Center or Strategic Asset?
12:35 - Transforming Conversations for Meaningful Outcomes
15:48 - Understanding Team-Specific Problems
19:37 - User-Centric Strategy for Agility
20:45 - Listening to Junior Insights
26:42 - Exploring Orchestration Layers in DOD