May 6, 2025 • 48 mins
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
29:50 - Accidental CEO Journey
31:25 - Effective Leadership and Team Retention
34:16 - Rigid Systems vs. Creative Context
38:11 - Breaking Creative Blocks
43:45 - "Evolving Perceptions and Reality"
45:25 - "Meeting People Where They Are"
47:26 - Outro
Key Takeaways:
Championing Cybersecurity Compliance
Empowering IT Operations
Creating Value with Technology
Culture and Innovation Go Hand in Hand
The Power of Listening
Quotes:
"Turning compliance into a value driver can revolutionize organizations and the entire industry."- Scott Shagory
"Solving the real problem unlocks true innovation and value."- Jason Young
Connect with Jason Young:
LinkedIn: https://www.linkedin.com/in/jason-paul-young/
Website: https://pylonsecure.com
Connect with the Host Scott Shagory:
http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:scott@purplefinchgroup.com
Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/
Powered by: http://heartcastmedia.com/
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
29:50 - Accidental CEO Journey
31:25 - Effective Leadership and Team Retention
34:16 - Rigid Systems vs. Creative Context
38:11 - Breaking Creative Blocks
43:45 - "Evolving Perceptions and Reality"
45:25 - "Meeting People Where They Are"
47:26 - Outro
Key Takeaways:
Championing Cybersecurity Compliance
Empowering IT Operations
Creating Value with Technology
Culture and Innovation Go Hand in Hand
The Power of Listening
Quotes:
"Turning compliance into a value driver can revolutionize organizations and the entire industry."- Scott Shagory
"Solving the real problem unlocks true innovation and value."- Jason Young
Connect with Jason Young:
LinkedIn: https://www.linkedin.com/in/jason-paul-young/
Website: https://pylonsecure.com
Connect with the Host Scott Shagory:
http://purplefinchgroup.com
http://linkedin.com/in/scottshagory
Email: mailto:scott@purplefinchgroup.com
Sponsor: Purple Flinch Group
https://www.purplefinchgroup.com/
Powered by: http://heartcastmedia.com/
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