Root To CISO

17:31

Cybersecurity Comes With Pressure. Here's How You...

Root To CISO ·

2026/10/06

Cybersecurity comes with pressure. So how do you manage it without letting it take over? In this Root To CISO Bite Size episode, we bring together perspectives from experienced cybersecurity leaders on managing stress, knowing when to switch off, and finding ways to stay grounded through demanding periods in your career. You’ll hear conversations about: 🔹 Why lean security teams can create additional pressure, and why cyber professionals sometimes make it harder on themselves by always

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38:51

Leadership Is More Than a Title. This is What...

Root To CISO ·

2026/09/29

Getting the leadership title is one thing. Knowing how to lead when the decisions get harder is another. In Part 2 of our conversation with Yonesy Nunez, Kris Rides digs into what leadership actually looks like once you are responsible for people, risk, business decisions and the problems you inherit. Strong leadership is not about being the person who always says yes, it is not about being the person who always says no either. It is about understanding the problem, knowing the risk, and bein...

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37:09

How The Experience You Dismiss Could Shape Your...

Root To CISO ·

2026/09/22

What if the job you think is “just a job” is actually the experience that changes your entire career? In this episode of the Root To CISO Podcast, Kris Rides sits down with Yonesy Nunez, to unpack the unconventional career path that took him from folding mail and teaching himself a programming language over one weekend to becoming a cybersecurity executive. Yonesy Nunez didn’t start out planning to become a CISO. He started in accounting, discovered computing, worked multiple jobs while at un...

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10:58

If I Could Start My Career Again, I’d Do These Things...

Root To CISO ·

2026/09/15

What career advice only makes sense once you’ve lived through it? In Part 2 of our “advice to your younger self” series, experienced cybersecurity leaders shares these career lessons they wish they had understood earlier, so you can make more informed decisions. From building relationships with people who can advocate for you, to getting comfortable around senior executives, knowing when loyalty is keeping you in the wrong place, and staying open to opportunities you never thought you w...

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33:24

As AI Changes Cybersecurity, What Will Set You Apart?...

Root To CISO ·

2026/09/08

How is AI changing cybersecurity, and what does that mean for the modern CISO? In Part 2 of this Root to CISO conversation, Kris Rides and AJ Debole look at how artificial intelligence is changing the pressure, priorities and expectations facing cybersecurity leaders. AJ argues that while much of AI security still comes back to first principles, access control, segmentation, patching and strong security fundamentals, the scale and speed of the challenge are changing dramatically. The conversa...

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31:44

Breaking Into Cybersecurity By Starting With What You...

Root To CISO ·

2026/09/01

What happens when the experience you already have starts to make sense in a completely different career? In this episode of Root to CISO, Kris Rides sits down with AJ Debole, Field CISO at Oracle Cloud, to talk through a career journey shaped by curiosity, unexpected decisions, persistence and experience gained far beyond cybersecurity. AJ started out studying political science before going to law school, joining the Army Reserve and later working in telecom, procurement and logistics. Cybers...

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12:15

Career Advice These CISOs Wish They Had Earlier In...

Root To CISO ·

2026/08/25

What do experienced CISOs wish they had known at the beginning of their cybersecurity careers? In this bite-sized episode, Kris Rides looks back at conversations with cybersecurity leaders over the years and brings together one question we ask every guest: What advice would you give your younger self? and their answers reveal lessons that often take years of experience, career changes, mistakes and leadership to fully understand. From learning to take more risks and ask harder questions...

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39:30

Building A Cybersecurity Career That Adapts To Change...

Root To CISO ·

2026/08/18

How do you build a cybersecurity career that can adapt when the industry around you keeps changing? In this episode of Root to CISO, Kris Rides continues his conversation with John Masserini, cybersecurity consultant and experienced security leader, to explore what decades of change in cybersecurity can teach us about building a career that lasts. Throughout his career, John has had to adapt to different industries, technologies, regulations and responsibilities. From the early days of cybers...

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32:00

You Have The Cybersecurity Certification But What Can...

Root To CISO ·

2026/08/11

What does it actually take to build a successful career in cybersecurity? In this episode of Root to CISO, Kris Rides sits down with John Masserini, cybersecurity consultant and experienced security leader, to unpack the real-world skills, experiences, and career decisions that shaped his journey into cybersecurity. He talks about how his career did not begin with a cybersecurity degree or a perfectly defined career path and how he worked in programming and banking, worked across application ...

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10:04

The Number #1 Skill Every Successful CISO Has Than No...

Root To CISO ·

2026/08/04

Cybersecurity professionals are taught to focus on tools, threats, and technical expertise. While it's important to have technical skill, the reality is that for you to advance you need this In this week's episode we recap a cybersecurity skill that has come up almost in all our chats with successful CISO and one thing is clear. The most successful security leaders aren’t just technical experts, they understand the business inside and out and know how to align their work to business objective...

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33:06

How To Identify What Is For You And Move On From One...

Root To CISO ·

2026/07/28

In today’s part 2 episode of our chat with Zachary Lewis, CIO & CISO at the University of Health Sciences and Pharmacy in St. Louis, we go deeper into the side of cybersecurity careers most people avoid talking about: what happens when the role you took turns out to be the wrong one. From walking into an understaffed team that couldn’t hire, to navigating internal politics, leadership misalignment, and roles that look good on paper but fall apart in practice, this conversation breaks down...

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33:27

Stop Waiting For Opportunities And Start Taking...

Root To CISO ·

2026/07/21

Most people are waiting for the "right opportunity” but most times, you have to create the opportunity yourself. In this week's episode of the Root to CISO podcast, Zachary Lewis breaks down how taking initiative early completely changed the trajectory of his career. From fixing computers in high school to stepping into leadership roles across IT and cybersecurity, he had never been one to just wait for the opportunities he wanted. He approached companies directly, started a side business bef...

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15:53

Why Taking a “Step Back” Might Be A Smart...

Root To CISO ·

2026/07/14

In today's episode, we take a look into the stories of senior cybersecurity leaders we've had the privilege of talking. We unpack a reality most people don’t talk about: the best career moves often look like steps backward. From turning down higher-paying roles and CISO titles… to choosing opportunities that offer more learning, impact, and long-term growth, this conversation breaks down what it really means to think long-term in cybersecurity. They get into: 📌 Why “backward” or sideways

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36:11

You Don’t Need Another Cybersecurity Certification…Do...

Root To CISO ·

2026/07/07

Certifications feel like progress… but this episode shows why they’re often not what actually moves your career forward. In part 2 of our conversation with Adam Robertson, VP of Enterprise Technology & Information Security at Virgin Galactic, he unpacks what really creates momentum in a cybersecurity career and why relying on certifications alone can leave people feeling stuck. As he reflects on his own journey, from early roles through to leadership, it becomes obvious that the big...

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33:09

The Cybersecurity Advice That Seems Obvious But Most...

Root To CISO ·

2026/06/30

If you want to grow fast in cybersecurity, put yourself in situations where you’re forced to learn. In this episode of Root to CISO, Kris sits down with Adam Robertson, VP of Enterprise Technology & Information Security at Virgin Galactic, to break down what his cybersecurity career journey looks like. He had no perfect roadmap, no textbook progression, just real decisions, real risks, and real growth. From starting out as an apprentice and getting made redundant during the dot-com ...

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14:02

Unconventional Journeys to Cybersecurity Leadership |...

Root To CISO ·

2026/06/23

Want to become a CISO? Sometimes things don't go as planned and it's oka In this bite-sized episode of Root to CISO Byte Size, we recap the career journeys of some cybersecurity leaders. They share their real career journeys, from finance, helpdesk, government, and consulting into senior security leadership roles. You’ll learn why there’s no single path into cybersecurity leadership, and what actually matters if you want to stand out and progress. The episode covers: * How these CISOs act...

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35:57

The Leadership Lessons No One Teaches You in...

Root To CISO ·

2026/06/16

What does it really take to become a great leader in cybersecurity? In this episode of the Root to CISO Podcast, Kris Rides sits down for part 2 with Jenai Marinkovic to break down more of her career and the real traits, habits, and mindset that separate average professionals from exceptional leaders in cybersecurity. From building side projects and leading without authority to thinking differently and creating your own opportunities, this episode is packed with practical advice for anyone lo...

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31:35

This Career Mistake Slows Many Cybersecurity...

Root To CISO ·

2026/06/09

What does it really take to become a CISO? In this episode of the Root to CISO Podcast (Season 3), we sit down with Jenai Marinkovic, a cybersecurity leader with over 25 years of experience, vCISO at our company, Tiro Security & CEO, GRCIE. Jenai, breaks down the reality behind building a career in cybersecurity leadership. She shares how she entered cybersecurity in the early days of the internet and worked her way through nearly every role in the industry, from engineering and architect...

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18:44

How To Become A CISO & What Top CISOs Actually Look...

Root To CISO ·

2026/06/02

In this episode, we speak to leading Chief Information Security Officers and we ask them to break down the real skills, mindset, and strategies behind successful cybersecurity careers from their personal experience. If you're aiming for a CISO role or growing in cybersecurity, this episode covers: The top skills every CISO needs (beyond technical knowledge) Why communication, curiosity, and likability matter more than you think How to build trust and influence stak...

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7:57

How To Advance And Get Promoted In Cybersecurity |...

Root To CISO ·

2026/05/26

Relying solely on technical skills and certifications is no longer enough to scale your career. In this episode of Root to CISO, top security executives break down the mindset, attitude, and connections needed to advance into cybersecurity leadership. Melina Scotto shares her personal journey, explaining why saying "yes" to unexpected opportunities is a major career catalyst. She narrates how a close professional connection opened the door to a major job opportunity—proving that relationships...

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