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 development and data center operations, and eventually found himself responsible for securing an early online stock-trading platform. 

John also challenges the idea that a cybersecurity degree, certification, or a long list of credentials automatically makes someone job-ready. He explains why hands-on experience matters, why cybersecurity professionals need to keep learning as the threat landscape changes, and why CISOs should invest in structured internship programs to develop the next generation of cybersecurity talent.

In this conversation, we explore:

🔐 How and why cybersecurity education and real-world experience can be very different
🔐 Why hands-on practice can matter more than credentials alone
🔐 How internships can help develop stronger cybersecurity talent
🔐 How working across different roles helps shape careers
🔐 Why continuous learning matters in a rapidly changing cybersecurity industry
🔐 How cybersecurity professionals can become more valuable beyond certifications

Whether you are starting your cybersecurity career, considering a move into cybersecurity, hiring cybersecurity professionals, building an internship program, or already working as a security leader, this episode offers a practical look at what actually helps people succeed in the field.

🎙️ Listen to Part 1 of our conversation with John Masserini on Root to CISO and look out for part 2!

 #RootToCISO #Podcast #Cybersecurity #CybersecurityCareers #CISO #CyberSecurityJobs #CybersecurityLeadership 

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 objectives.

In this episode the conversation goes beyond technical skills and dives into  learning how organizations make money, understanding executive priorities, incentives, and objectives, and aligning with business operations and teams outside cybersecurity. 

The episode explores how cybersecurity professionals can align their work with what actually drives a company forward, because security doesn’t operate in isolation. Every control, every decision, and every risk has a direct impact on business performance.

You’ll also learn why strong communication and listening skills are critical, how to build trust across departments like HR, marketing, and sales, and how aligning with executive goals can help you deliver both security outcomes and business value.

Here is what stands out in the episode:

• Why cybersecurity professionals must understand the business extensively
• How CISOs align security with executive objectives
• The importance of communication and stakeholder management
• Turning cybersecurity into a business enabler
• Translating technical risk into business impact
• Building trust across teams and departments

If you want to move beyond being seen as “just technical” and start influencing real decisions, this episode gives you a clear perspective on how to do it. Whether you’re early in your cybersecurity career or aiming for a leadership role, understanding the business is not optional. It’s the foundation for long-term success.

Listen to the full episode and follow for more insights from cybersecurity leaders and hiring managers on how to grow your career and stand out in the industry.

#RootToCISO #Podcast #Cybersecurity #Leadership #CareerGrowth #BusinessUnderstanding

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 what it really means to recognize when something isn’t working and make a move.

They get into:

📌 The red flags you should be looking for before accepting a role
 📌 Why some environments make it impossible to succeed, no matter how good you are
 📌 The hiring dysfunction that leaves teams stuck and overworked 
 📌 Why staying out of loyalty can do more harm than leaving
 📌 How to think about short tenures and explain them without damaging your career

This episode also dives into real-world leadership challenges, from rebuilding teams during uncertainty to navigating rapid change, including scaling infrastructure during COVID and responding to a ransomware incident.

If you’re in a role that doesn’t feel right, or you’re evaluating your next move, this episode will help you ask better questions, spot problems earlier, and make decisions that actually move your career forward.

🎧 Share this with someone who’s trying to figure out whether to stay or leave.

#RootToCISO #Podcast #CyberSecurity #CyberSecurityCareers #CISO #CareerDecisions #CyberSecurityJobs #Leadership

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 before even graduating, took on extra roles just to learn, and worked night shifts while building his experience. None of it was part of a perfect plan, but it all compounded.

If you’re trying to break into cybersecurity, IT, or level up in your career, this episode shows what actually makes the difference. It’s not just skills or certifications, it’s what you do when no one is asking you to step up.

They also chat about:

•  How to create opportunities instead of waiting for them 
•  Why early initiative matters more than experience 
•  The real reason some people progress faster than others 
•  How taking on “extra” work can accelerate your career 
•  Building momentum before you feel ready 

This is for anyone stuck waiting, applying, or unsure what their next move should be.

#RootToCISO #Podcast #CareerAdvice #CybersecurityUSA #Leadership #Hiring #CybersecurityPodcast

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 moves can accelerate your career
 📌 How to evaluate opportunities beyond salary and title
 📌 The importance of learning vs. optics in career decisions
 📌 Why trusting your gut matters more than external validation
 📌 How to think about trade-offs: what you gain vs. what you give and how to make a decision

Successful career journeys aren’t about perfect plans or climbing a straight ladder. They are about making intentional decisions, staying curious, and putting yourself in environments where you can grow, even if it doesn’t make sense to everyone else and looks like a step backward.

If you’re early in your career, feeling stuck, or questioning your next move, this episode will help you reframe how you think about progress.

🎧 Share with someone who might need to hear this!

#RootToCISO #Podcast #CyberSecurity #CyberSecurityCareers #CISO  #CareerGrowth #CyberSecurityJobs #Leadership 

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 biggest opportunities didn’t come from what was on his CV, they came from being in the right environments, building relationships, and putting himself in positions where things could happen.

We get into:

•  Why certifications help you get started, but won’t move your career on their own 
•  How the “learn, certify, apply” model is becoming less effective 
•  The role networking and proximity play in unlocking real opportunities 
•  The value of broad experience across cybersecurity domains 
•  Why specializing too early can limit your long-term growth 
•  Why fundamentals matter more than chasing the next certification or trend 

If you’re trying to break into cybersecurity or figure out why your progress feels slower than expected, this episode offers a more honest perspective on what actually makes the difference.

Certifications aren’t the problem, but they’re not the solution either.

🎧 If you haven’t watched Part 1 yet, go back and start there, it sets the foundation for everything discussed in this episode.

#RootToCISO #CyberSecurity #CISO #CareerGrowth #CybersecurityCertifications  #Leadership #Hiring #CyberSecurityTips 

 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 crash… to breaking into cybersecurity through certifications, landing a SOC role, moving across industries, and eventually stepping into executive leadership — Adam’s journey is anything but linear.

They get into:

• How he broke into cybersecurity without a degree
• How certifications opened doors for him early on
• The real role networking plays in landing leadership opportunities
• Why “luck” sometimes matters, and how to create your own
• What consulting teaches you that full-time roles don’t
• Why mastering the basics matters more than chasing trends

If you’re trying to get into cybersecurity, grow into leadership, or eventually become a CISO, this episode gives you a real-world perspective on what it actually takes.

No shortcuts. No perfect plans. Just consistent learning, smart moves, and putting yourself in the right rooms.

🎧 Part 2 drops next week — make sure you’re subscribed so you don’t miss it.

#RootToCISO #CyberSecurity #CISO #CyberSecurityCareer #InfoSec #CareerGrowth #TechCareers #CyberSecurityJobs #Leadership #CyberSecurityTips 

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 actually started their careers (it’s rarely cyber first)
* How sideways and backwards career moves are shape your career
* Learning by doing, figuring things out before feeling “ready”
*  Taking opportunities others would hesitate to take (even without full experience)
* Treating every role like ownership, not just a job

Whether you're starting out in cybersecurity or aiming for leadership, this episode breaks down the mindset, decisions, and experiences that shape top CISOs.

Subscribe for more insights from real cybersecurity leaders.

#CISO #CyberSecurityCareer #InfoSec #CyberSecurityLeadership #GRC #TechCareers

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 looking to step into leadership roles like CISO.

💡 One of the biggest takeaways:
 Great leaders aren’t given opportunities, they create them.

🔑 In this episode, you’ll learn:

•  How to stand out in a highly competitive cybersecurity job market 
•  Why side projects are critical for leadership growth 
•  The mindset shift required to move into leadership roles 
•  How to lead even when you don’t have the title 
•  Why networking and visibility matter more than your CV 
•  The real impact of AI on cybersecurity careers and entry-level roles 

🎯 Who this is for:

•  Aspiring CISOs 
•  Cybersecurity professionals looking to level up 
•  Anyone looking to level up in their career and climb up the ladder
•  Leaders wanting practical, real-world advice 

📢 Call to Action:

If you’re serious about growing your career in cybersecurity, make sure to subscribe and follow the Root to CISO podcast for more real conversations with top industry leaders.

#RootToCISO #Podcast #CISO #CareerAdvise #Leadership

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 architecture to investigations, leadership, and eventually CISO-level responsibility.

We dive into:

•  How to transition from individual contributor → team lead → manager → director
•  The biggest mistakes leaders make (and what it actually takes to grow) 
•  Why understanding the business matters more than technical skills
•  The challenge of letting go and leading through others
•  Why linear career paths can limit your growth

If you're trying to break into cybersecurity, move into leadership, or become a CISO, this episode gives you a real, unfiltered look at the journey.

🎧 Part 1 of 2 — Part 2 coming next week

#RootToCISO #Cybersecurity #Leadership #CareerSuccess