Root To CISO

Kris Rides
  • 5.0 (2)
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Do you aspire to become a Chief Information Security Officer?The Root to CISO podcast provides firsthand career stories from experienced CISOs on their journey to success in the cybersecurity industry.  Offering valuable guidance for aspiring professionals in the field through personal experiences and practical advice. 

  1. 1d ago

    Building A Cybersecurity Career That Adapts To Change | Root To CISO Podcast

    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 cybersecurity consulting to protecting Dow Jones and The Wall Street Journal, building the security program for a new stock exchange, and leading security across multiple countries, each move required him to understand a new environment and respond to a different set of challenges. His experience shows why succeeding in cybersecurity is not simply about what you know today. Professionals need to remain curious, get hands-on with technology, understand how different businesses operate, build relationships within the industry and be willing to keep learning as their responsibilities change. In this conversation, we explore: 🔐 Why adaptability becomes increasingly important as cybersecurity changes 🔐 How working across different industries can make you a stronger security professional 🔐 Why curiosity and hands-on experience matter when starting a cybersecurity career 🔐 Why networking and participating in the cybersecurity community can create career opportunities 🔐 How mentorship can shape your career and why giving back matters as you become more experienced 🔐 How to navigate major career transitions and find new ways to use your experience Whether you are trying to break into cybersecurity, looking for your next opportunity, moving into leadership, or figuring out what the next stage of your career looks like, this episode offers practical lessons on building a career that can evolve with you and the industry. 🎙️ Listen to Part 2 of our conversation with John Masserini on Root to CISO. #RootToCISO #Podcast #Cybersecurity #CybersecurityCareers #CISO #CybersecurityLeadership #CareerAdvice

  2. Aug 11

    You Have The Cybersecurity Certification But What Can You Do With It? | Root To CISO Podcast

    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

  3. Aug 4

    The Number #1 Skill Every Successful CISO Has Than No One Teaches You | Root To CISO Podcast

    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 extensivelyHow CISOs align security with executive objectivesThe importance of communication and stakeholder managementTurning cybersecurity into a business enablerTranslating technical risk into business impactBuilding trust across teams and departmentsIf 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

  4. Jul 28

    How To Identify What Is For You And Move On From One That Isn’t | Root To CISO Podcast

    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

  5. Jul 21

    Stop Waiting For Opportunities And Start Taking Initiative | Root To CISO Podcast

    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

  6. Jul 14

    Why Taking a “Step Back” Might Be A Smart Cybersecurity Career Move | Root To CISO Podcast

    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

  7. Jul 7

    You Don’t Need Another Cybersecurity Certification…Do This Instead | Root To CISO Podcast

    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

  8. Jun 30

    The Cybersecurity Advice That Seems Obvious But Most People Ignore | Root To CISO Podcast

    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 degreeHow certifications opened doors for him early onThe real role networking plays in landing leadership opportunitiesWhy “luck” sometimes matters, and how to create your ownWhat consulting teaches you that full-time roles don’tWhy mastering the basics matters more than chasing trendsIf 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

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About

Do you aspire to become a Chief Information Security Officer?The Root to CISO podcast provides firsthand career stories from experienced CISOs on their journey to success in the cybersecurity industry.  Offering valuable guidance for aspiring professionals in the field through personal experiences and practical advice. 

Information

  • Creator
    Kris Rides
  • Years Active
    2024 - 2026
  • Episodes
    88
  • Rating
    Clean
  • Copyright
    © 2026 Root To CISO
  • Show Website
    Root To CISO