When it comes to the cybersecurity field, one question I’m continually asked isn’t how companies should prepare a cyber defence or what threats are most likely to disrupt organisations and society within the region—it’s how to break into and land a job in cybersecurity, specifically in the Caribbean.
The answer is both simple and more complex than it appears. Sure, I could tell you to earn core networking and basic cybersecurity certifications—and that wouldn’t be wrong—but it would be pedestrian at best. Yet, pedestrian has its place.
Breaking into cybersecurity isn’t easy or straightforward, especially for beginners. Like every challenge in life, you’ll need a strategy. These three steps are what I recommend to get started.
The field can feel both exciting and overwhelming with its mix of technical complexity and ever-evolving threats. Knowing where to start is half the battle.
The best advice I can offer upfront is this: be patient. The cybersecurity job market—especially in the Caribbean—is still maturing, and the demand for specialist skills is growing but uneven. Don’t let that discourage you; it just means that timing, strategy, and persistence are key.
That said, here’s a practical, three-step roadmap for entering the cybersecurity space—even with little or no prior experience.
Build a Solid Foundation
A cybersecurity career begins with mastering the core building blocks of information technology. A solid grasp of networking concepts, operating systems (particularly Linux and Windows), and system administration is essential to understanding how digital environments function—and how to secure them.
Hands-on experience is just as important. Setting up a home lab using virtual machines (VMs) allows you to simulate cyberattacks, test tools, and learn detection techniques. Free and open-source platforms like Wireshark, Metasploit, and Wazuh offer practical learning opportunities.
Online platforms like TryHackMe, Cybrary, and Hack The Box provide guided labs and gamified challenges that blend theory with applied skill. Capture the Flag (CTF) competitions or volunteering with small businesses for basic assessments can also build confidence and credibility.
To round out your foundation, consider certifications like CompTIA Security+ or ISC2’s Certified in Cybersecurity (CC). These are globally recognised and demonstrate your commitment to learning—an asset when applying for your first role.
Personal Brand and Industry Knowledge
Let’s face it—most business leaders can’t clearly distinguish the roles of a network administrator, a CTO, or a cybersecurity analyst. To many, they all sound the same. That’s why it’s often difficult for newcomers to articulate their value.
Breaking into the field requires more than just technical skills—it demands a clear understanding of the industry you intend to protect. While it’s natural to be eager to apply your newly acquired cybersecurity skills, the real question is: How can you effectively defend an industry you don’t fully understand? To be successful, you must be able to apply your cybersecurity knowledge within the context of that specific sector.
Take healthcare, for example. If you’re applying for a role in a hospital’s IT department but lack familiarity with healthcare terminology, systems, or compliance requirements, you’ll struggle to connect with their real-world needs. In such cases, an additional certification like the Certified Health Data Analyst (CHDA®) can set you apart.
The CHDA credential demonstrates your ability to analyse and interpret health data and align cybersecurity practices with both strategic goals and operational realities—something hiring managers value in specialised sectors.
For those already working in an industry, consider pivoting internally. Existing institutional knowledge often makes it easier to transition into a cybersecurity role within the same sector.
Thought Leadership: Share Your Voice, Shape Your Brand
Skills and certifications matter—but they don’t tell your full story. I’ve met many bright, ambitious professionals with identical credentials and similar hobbies. What sets people apart is how they share their journey and communicate their perspective.
Employers aren’t just hiring skills; they’re aligning with individuals whose values and vision match their own. Just as consumers are drawn to brands they identify with, businesses connect with professionals who are visible, intentional, and authentic.
This is where thought leadership becomes your edge.
Whether you’re blogging, posting insights on LinkedIn, sharing videos on YouTube, or maintaining a GitHub repository, documenting your journey publicly shows curiosity, growth, and commitment. It helps people understand not just what you know, but how you think.
Thought leadership isn’t about being an expert—it’s about being consistent, reflective, and willing to share. That’s how you build credibility and stand out in a field full of people with similar qualifications.
Charting your path in cybersecurity
Breaking into cybersecurity—especially within the regional context—isn’t about following a rigid formula. It’s about crafting a strategy that aligns technical growth with industry understanding and personal storytelling.
By building a solid foundation, developing sector-relevant knowledge, and using thought leadership to make your journey visible, you become more than a job seeker. You become someone who brings value, vision, and voice to the organisations you hope to serve.
The field is evolving, and so should you. Whether you’re starting from scratch or pivoting from another role, remember that in cybersecurity, your journey is part of your value. Own it, share it, and use it to unlock doors others don’t even see.
Steven Williams is the executive director of Sunisle Technology Solutions and the principal consultant at Data Privacy and Management Advisory Services. He is a former IT advisor to the Government’s Law Review Commission, focusing on the draft Cybercrime bill. He holds an MBA from the University of Durham and is certified as a chief information security officer by the EC Council and as a data protection officer by the Professional Evaluation and Certification Board (PECB). Steven can be reached at Mobile: 246-233-0090; Email: steven@dataprivacy.bb
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