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 being able to say: “Here are our options. Here is what each one means. Here is how we can move forward.”

Yonesy also shares lessons from six stints as a CISO on becoming the kind of leader who removes roadblocks instead of creating them, gives people room to grow, communicates difficult decisions clearly, and keeps reassessing whether they are still learning, contributing and moving in the right direction.

🎯 In this episode, we explore:

🚧 Why simply shutting an idea down creates friction and why strong leaders bring alternatives.

🧠 How the job of a CISO is to untie knots, remove roadblocks and help people succeed while still protecting the organization.

🤝 What kind of environment you should create for your people as a leader.

📈 Why your job title should never become your identity.

🔄 How leadership sometimes requires you to rethink your next move

💬 How to communicate with executives and boards

This one is for those already leading a team, preparing for their first leadership role, moving toward cybersecurity leadership, or wondering what separates a title-holder from someone people genuinely trust to lead.

Watch the full conversation and ask yourself:

When someone brings you a problem, are you the person who creates another roadblock, or the person who helps find the way through?

🎧 Listen to the full episode

Know someone stepping into leadership, managing a team or preparing for a bigger role? Send this episode to them.

Remember to subscribe to Root To CISO for more conversations on cybersecurity leadership, CISO careers, executive decision-making, hiring, career growth and what it actually takes to lead in cybersecurity.

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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 university, and eventually found himself in cybersecurity after a SANS conference gave him the skills to start testing what he had learned.

And if you’re wondering whether your current experience, first job or career detour actually matters, this conversation gives you plenty to think about.

🎯 In this episode, we explore:

💼Why practical cybersecurity experience can sometimes teach you what a degree or certification cannot.

📚 Why pursuing training and hands-on experience before certifications can be a good alternative

🙋 Why putting your hand up, taking ownership and actually delivering can shape your career long before you have a leadership title.

🤝 How leadership is about building an ecosystem where other people can grow, contribute and succeed

If you’re starting out in cybersecurity, trying to break into the industry, wondering whether experience matters more than another certification, or thinking about your eventual path into cybersecurity leadership, there’s something in this conversation that may change how you look at your next career move.

Watch/listen to the full conversation and then tell us: what’s one opportunity you almost overlooked that ended up changing your career?

Know someone trying to break into cybersecurity or figure out their next career move? Send this episode their way.

And if you’re building a career in cybersecurity, subscribe to Root To CISO for more real career journeys, cybersecurity leadership lessons, hiring insights and conversations with the people behind the titles.

#RootToCISO #CybersecurityCareers #Cybersecurity #CISO #CybersecurityLeadership #CybersecurityCareer #CareerAdvice

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 wanted.

In this conversation, we explore:

• Why having advocates inside your company can strengthen your ideas and accelerate your growth
• Why chasing meaningful work and development can matter more than chasing the next paycheck
• How staying too loyal to the wrong situation can hold your career back
• Why early exposure to executives can change how you communicate, think and lead
• How trying roles you think you won’t enjoy can reveal career paths you never considered
• Why being open to unexpected opportunities can make you more skilled, adaptable and marketable
• How relationships, reputation and consistently good work often create the “luck” people credit for career success

If you’re early in your cybersecurity career, considering your next move, or trying to work out what direction you want to take, these are the lessons worth hearing before experience teaches them the hard way.

Have a listen, share and subscribe for more cybersecurity career advice, hiring insights and lessons from people who have built successful careers in the industry.

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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 conversation also explores what this shift means for leadership.

As AI introduces new security risks and new operational questions, AJ believes the future of cybersecurity will need more than one type of CISO. Technical expertise matters, strategy matters, compliance matters but so do different backgrounds, different ways of thinking and people who can approach unfamiliar problems from new perspectives.

In this episode, we explore:

• How AI is changing cybersecurity leadership
• How AI could change attack and the way organizations prioritize security risks
• Why disrupting attacks may become as important as preventing and recovering from them
• How CISOs can prepare organizations for increased demands
• What new AI security risks mean for security teams
• Why the modern CISO may need a broader mix of skills and perspectives
• Why cybersecurity teams will increasingly need people from different professional backgrounds
• How AI continues to reshape cybersecurity careers and leadership

As cybersecurity changes, the leaders who succeed may be the ones who can combine strong fundamentals with adaptability, broader perspectives and the ability to solve problems the industry does not yet have perfect answers for.

Subscribe to Root to CISO for more conversations with cybersecurity leaders about the realities of security leadership, career growth and the future of the industry.

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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. Cybersecurity was not part of the original plan and her interest began much later, through cryptocurrency, Ethereum and cryptography, before an opportunity within the military introduced her to cyber more directly.

From there, the transition was anything but immediate.

Her story raises an interesting question for anyone thinking about where their own career could go next: how much of the experience you already have might become valuable in ways you cannot see yet?

In this conversation, we explore:

• What moving across different industries can teach you about building a career in cybersecurity
• How experience gained in one field can become relevant when you move into another
• The ways curiosity can pull your career in directions you never originally planned for
• Why the path people are advised to follow is not always the path that actually shapes successful careers
• What preparation looks like when the right opportunity finally appears
• How the experience you are building now could become more valuable later than you realize

If you’re trying to enter cybersecurity, considering a career change or simply unsure how the experience you already have fits into where you want to go next, this episode offers a useful reminder: careers often make more sense looking backwards than they do while you are building them.

Subscribe to Root to CISO for more conversations with cybersecurity leaders about the experiences, decisions and moments that shaped their careers.

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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 to staying curious, being intentional about your priorities and understanding that no single career decision has to define your future, these CISOs share what they wish they had understood sooner.
In this episode, we explore:

🔐 Why learning to say no can be just as important as saying yes to opportunities
🔐 Why fear of failure can hold you back early in your cybersecurity career
🔐 How to think about career risks, failures and decisions that can be changed versus those that cannot
🔐 Why your first job or career decision does not have to determine the rest of your career
🔐 Why constantly chasing the next role can stop you from appreciating and learning from where you are now
🔐 How staying curious and continuing to ask “why?” can help you build deeper cybersecurity expertise and create more career opportunities
🔐 Why younger professionals should have the confidence to ask difficult questions about salary, expectations, reporting structures and opportunities before accepting a role

There is no perfect roadmap to becoming a CISO, and many of the lessons that shape successful cybersecurity careers only become obvious in hindsight.

Whether you are trying to break into cybersecurity, starting your first security role, considering your next career move or working toward cybersecurity leadership, this episode brings together practical advice from experienced CISOs for the professionals following behind them.

🎙️ Watch the latest episode of Root to CISO and hear the career advice these cybersecurity leaders would give their younger selves and comment what you wish you knew in your earlier career.

#RootToCISO #Podcast #Cybersecurity #CybersecurityCareers #CISO #CareerAdvice #Leadership  #CyberecurityRecruiter

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 

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.

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