Root To CISO

You can spend years building a successful career, gaining experience, earning promotions, and doing work you love, only to find yourself unemployed because of circumstances completely outside your control. What happens when the career you've worked so hard to build suddenly takes an unexpected turn?In this episode of Root to CISO, Kris Rides sits down with Dennis Dayman, a seasoned cybersecurity leader who has spent decades working in internet security, policy, and the startup world.Dennis shares how his career began with a background in criminal justice and a personal interest in technology, eventually leading him to AT&T, where he rose to a senior leadership position. He later left to join Mail Abuse Prevention Systems (MAPS), working alongside some of the pioneers of the early internet on projects that helped shape online security.But just two years into that opportunity, the dot-com bubble burst. Dennis was laid off the day before his twins were born, and what followed was nearly a year away from his cybersecurity career, including working at Walgreens to make ends meet.Looking back, Dennis sees that difficult period differently, and his experience raises an important question: How do you navigate career setbacks when your experience and accomplishments aren't enough to protect you from them?In Part 1, Kris and Dennis discuss:Why building a successful career doesn't necessarily guarantee job security, The risks and rewards of stepping away from an established career to pursue new opportunitiesHow curiosity, continuous learning, and a willingness to take on unfamiliar challenges can prepare you for opportunities you never anticipated.Why career setbacks aren't always a reflection of your abilities, performance, or the decisions you've made.How difficult career experiences can change your perspective on success, professional fulfilment, and what really matters.Why navigating uncertainty and adapting to change are important at every stage of a cybersecurity career.This conversation is a reminder that even the most accomplished professionals experience career setbacks. Sometimes, the hardest part isn't losing a job but figuring out what comes next when the future you had planned suddenly looks different.Share this episode with someone who's struggling with uncertainty in their career and subscribe to Root to CISO for more honest conversations with cybersecurity leaders about the experiences, decisions, and challenges that shaped their careers.#RoottoCISO #CybersecurityCareers #CybersecurityLeadership #CareerSetbacks #CISO

What does it really take to move from an individual contributor to a cybersecurity leader, and is management actually the right next step for you?In this Root to CISO Bite Size episode, Kris Rides speaks with experienced cybersecurity leaders about the shift from doing the work yourself to leading people, influencing decisions and taking accountability for outcomes. The conversation makes one thing clear: leadership is not simply a title, a promotion or telling people what to do. It asks for a different kind of responsibility.Before pursuing a management role, it helps to understand what you are moving toward. Great leaders need self-awareness: knowing what they are good at, where they need support, what work gives them energy, and whether they genuinely want the pressure that comes with being responsible for a team. Sometimes the right path is leadership; other times, remaining an individual contributor can be equally rewarding.The episode also explores how leadership can begin long before your first manager title. Building trusted relationships, learning to influence people who do not report to you, taking on difficult work, giving others space to contribute, and staying accountable when something goes wrong are all signals that you are ready for more responsibility.In this episode, we explore:What changes when you move from cybersecurity practitioner to people leaderWhy self-awareness should come before the pursuit of a management titleHow to build leadership skills while you are still an individual contributorThe role of trust, relationships and influence in cybersecurity leadershipWhy leaders must take accountability instead of passing blame to their teamsHow to give feedback while creating an environment where people can growWhy taking on difficult, complex work can build experience and credibilityHow industry groups, committees and cross-functional work can create leadership opportunitiesWhether you are aiming for your first leadership role or deciding whether management fits the career you want, this conversation offers a more honest view of what leadership requires—and what you can start practicing now.Subscribe to Root to CISO for more conversations about cybersecurity careers, security leadership and the decisions that shape the people behind the work.#RootToCISO #Cybersecurity #CybersecurityLeadership #CISO #SecurityLeadership #CyberSecurityCareers #CareerGrowth #Leadership

What does it take to move from being good at cybersecurity to becoming the kind of leader trusted to shape the business?In Part 2 of our conversation with Rick Scott, Kris Rides continues the talk about what changes when your responsibility extends beyond security. It is no longer only about knowing what needs to be protected. It is about understanding how the business works, where it is trying to go, what risks it is willing to take, and how technology can genuinely help it get there.Rick shares what it has been like to hold both the Chief Information Security Officer and Chief Information Officer roles, from thinking differently about budgets and technology decisions to learning the importance of asking questions before trying to change a team or a process.The conversation also gets into the leadership skills that matter once you move beyond being an individual contributorIn this episode, we explore:What changes when a CISO takes on CIO responsibilities too.Why cybersecurity leadership has to be connected to business outcomesThe importance of understanding processes across the whole organizationWhy leaders should ask questions before making changesHow mentoring helps prepare professionals for leadershipWhat it means to support your team, even when their next opportunity is elsewhereWhy continuous learning, curiosity and listening matter throughout a cybersecurity careerIf you want to lead cybersecurity at a higher level, technical expertise is part of the foundation, but it is not the whole job. This conversation is a reminder that leadership means learning how to think more broadly, bring people with you, and help the business move forward securely.Subscribe to Root to CISO for more conversations about cybersecurity leadership, career growth and the future of the industry.#RootToCISO #Cybersecurity #CISO #CIO #CybersecurityLeadership #CyberSecurityCareers #Leadership

How much of what you say no to is based on what is actually in front of you, and how much is based on what you have experienced before?Sometimes an opportunity looks familiar enough that you think you already know what comes with it: the pressure, the responsibility, the environment and everything you have watched other people go through. But the same role in a different company, with different people and under different circumstances, can be a completely different experience.In Part 1 of this Root To CISO conversation, Kris Rides sits down with Rick Scott, Global CIO and CISO at Elevate Textiles, to talk about the career experiences that shaped the way he looked at leadership, why he once thought becoming a CISO was not for him, and what made him reconsider when the right opportunity came along.In this conversation, we explore:🔐 How past experiences can shape the opportunities you say yes or no to🔐 Why the same role can feel completely different depending on the company and environment🔐 How to assess an opportunity based on what is actually in front of you, not just what you have seen before🔐 Knowing when to take the leap and when saying no is still the right decision🔐 Why career growth sometimes means challenging the assumptions you have already made about yourselfWhether you are considering a new role, moving into leadership, or trying to work out what your next career step should be, this episode is a reminder not to limit yourself before you have properly understood the opportunity in front of you.🎧 Watch Part 1 of Rick Scott’s Root To CISO story and subscribe for more conversations about cybersecurity careers, leadership and the decisions that shape them.#RootToCISO #Cybersecurity #CybersecurityCareers #CISO #CybersecurityLeadership #CareerGrowth #InfoSec

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 trying to solve the next problem🔹 What pressure looks like from a leadership and founder perspective, especially when your team is depending on you🔹 Why stepping away and completely disconnecting can sometimes give you the reset you need🔹 The importance of exercise, routines and healthy outlets for managing stress🔹 Why having trusted people you can be honest and vulnerable with matters🔹 Learning to focus on what you can control and accepting that you can’t solve everythingPressure will look different depending on your role, responsibilities and stage of your career. The goal isn’t to eliminate it completely, but to find healthier ways to manage it while building a career that you can sustain for the long term.🎧 Watch the full episode for perspectives from cybersecurity leaders who have had to figure this out for themselves.Subscribe to Root To CISO for more honest conversations about cybersecurity careers, leadership, career growth and what it really takes to build a lasting career in the industry.#RootToCISO #Cybersecurity #CybersecurityCareers #CISO #CybersecurityLeadership

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 boardsThis 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 episodeKnow 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.#RootToCISO #CybersecurityLeadership #Leadership #CISO #CybersecurityCareers #CareerAdvice

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 succeedIf 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 successIf 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.#RootToCISO #Podcast #CybersecurityCareers #CareerAdvice #CISO #CybersecurityLeadership

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 leadershipHow AI could change attack and the way organizations prioritize security risksWhy disrupting attacks may become as important as preventing and recovering from themHow CISOs can prepare organizations for increased demandsWhat new AI security risks mean for security teamsWhy the modern CISO may need a broader mix of skills and perspectivesWhy cybersecurity teams will increasingly need people from different professional backgroundsHow AI continues to reshape cybersecurity careers and leadershipAs 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.#RootToCISO #Cybersecurity #CISO #AISecurity #CybersecurityLeadership #CyberSecurityCareers #AI 

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 realizeIf 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.#RootToCISO #Cybersecurity #CybersecurityCareer #CISO #CareerChange #CyberSecurityJobs