The Future of Cybersecurity Careers: Human Skills, AI Disruption & How to Stand Out Now

Episode 82 November 24, 2025 00:56:24
The Future of Cybersecurity Careers: Human Skills, AI Disruption & How to Stand Out Now
PrOTect It All
The Future of Cybersecurity Careers: Human Skills, AI Disruption & How to Stand Out Now

Nov 24 2025 | 00:56:24

/

Hosted By

Aaron Crow

Show Notes

The cybersecurity job market is changing faster than ever - and the skills that mattered five years ago won’t carry you into the future.

In this episode of Protect It All, host Aaron Crow sits down with Mark Sasson, Managing Partner at Pinpoint Search Group, to break down what the future of cybersecurity careers really looks like. From the rise of AI and automation to the growing importance of human skills, they uncover the new realities facing candidates, hiring managers, and leaders across IT and OT security.

You’ll learn:

Whether you’re entering cybersecurity, leveling up your role, or hiring your next team member, this episode delivers real-world, actionable insights to help you stay relevant  - and competitive in an evolving industry.

Tune in to learn how to stay ahead in the cybersecurity job market of today and tomorrow  only on Protect It All.



Key Moments: 

04:14 Recruitment Growth and Funding Trends

06:42 Tangible Value in AI Age

12:18 "Stepping Outside the Comfort Zone"

15:16 "Growth Through Embracing Discomfort"

19:23 "Embracing Growth and New Challenges"

21:01 Balancing Growth and Bold Moves

25:14 "Breaking Into Tech: Sacrifice & Strategy"

27:40 Experience Beats Book Knowledge

32:13 Human Insight Beats AI in Hiring

34:45 AI Recruitment: Potential, Limits, Distinctions

39:37 "Reluctant Growth through Opportunity"

42:47 "AI Tools: Benefits and Downsides"

44:29 "Human-Centered Hiring Over AI"

50:12 "Human Connection Over Technology"

53:23 "Planning Your Next Step"

About the guest: 

Mark Sasson is the Managing Partner of Pinpoint Search Group, a recruitment firm specializing in helping innovators in emerging markets attract the talent needed to drive maturation, scale, and successful outcomes. In 2014, Mark launched Pinpoint’s Cybersecurity practice, where he and his team have successfully completed hundreds of executive and senior-level individual contributor searches for leading Cybersecurity vendors. Building on that success, Mark is now guiding Pinpoint’s expansion into the rapidly evolving Space sector.

Connect Mark: 

Website: https://pinpointsearchgroup.com/

LinkedIn: linkedin.com/in/markjsasson/
Learn more about Cybersecurity Vendor M&A + Funding Roundups here : https://pinpointsearchgroup.com/cybersecurity-industry-reports/

Connect With Aaron Crow:

Learn more about PrOTect IT All:

To be a guest or suggest a guest/episode, please email us at [email protected]

Please leave us a review on Apple/Spotify Podcasts:

Apple   - https://podcasts.apple.com/us/podcast/protect-it-all/id1727211124

Spotify - https://open.spotify.com/show/1Vvi0euj3rE8xObK0yvYi4

Other Episodes

Episode 70

August 11, 2025 00:14:35
Episode Cover

Reflections from Black Hat and DEFCON: Trends, Community Energy, and the Future of OT Cybersecurity

In this episode, Aaron returns from an action-packed week at Black Hat and DEFCON in the sweltering heat of Las Vegas. He shares his...

Listen

Episode 40

January 10, 2025 00:41:48
Episode Cover

Why Small Events Like Staccato Ranch Outshine Big Conferences in Cybersecurity

In this episode, hosts Aaron Crow and Neal Conlon are joined by cybersecurity executive Ken Foster to discuss why smaller, focused events like the...

Listen

Episode 74

September 15, 2025 00:56:08
Episode Cover

Bridging Military and Civilian Cybersecurity: Leadership, Skills, and Lifelong Learning with Christopher Ross

In this episode, host Aaron Crow sits down with cybersecurity leader and National Guard threat hunt team lead Christopher Ross, diving into the real-world...

Listen