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

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:

Why soft skills, communication, and adaptability are now just as critical as technical expertise
How AI is reshaping job searches, resumes, and candidate evaluation
The shift between employer-driven and candidate-driven markets
What separates standout candidates in today’s competitive landscape
How startups think about hiring - and what they won’t compromise on
Practical steps to future-proof your cybersecurity career starting now

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: