From IC to Executive: Guidance From A Self-Taught Expert
Critical Stats
LinkedIn: Check out his profile!
Started their cybersecurity journey in: 1999
Most passionate about (in cybersecurity): Cyber defense, cyber offense, and cyber education
Favorite zero-day: One that I don’t have to defend against! LOL
Favorite song: “Good Riddance” by Green Day
Introduction
Kaustubh Kubde (also known as “KK” to his friends) brings over two decades of deep expertise to the cybersecurity landscape, having built his career from the ground up as a self-taught penetration tester. His journey in information security began with hands-on technical skills and has evolved into comprehensive executive leadership across multiple domains of cybersecurity.
We selected KK because he’s a cyber vanguard! Throughout his distinguished career, KK has demonstrated exceptional ability in establishing and scaling security operations, developing robust governance programs, and delivering strategic security evaluations and advisory services. His practical approach to cybersecurity, rooted in his technical origins, enables him to bridge the gap between complex security challenges and business outcomes. I have personally witnessed this in all my professional interactions with him; he is rather skilled.
Without further ado, we asked KK our standard set of 5 questions to rule them all, and here are his responses:
Five questions to rule them all!
1. What is the biggest problem we are dealing with in cybersecurity?
In business, the biggest challenge is not knowing what to protect. With threats that are constantly evolving, expanding technical debt, as well as digital sprawl, the attack surface continues to grow. However, many organizations lack a clear understanding of what’s critical, what's exposed, and what's quietly eroding under the radar. You can't defend what you don't see.
For society, the challenge is context. We are aware of cyber threats, but we often fail to understand their impact on us fully. Will a breach shut down my city's power grid or drain my bank account? Until we can connect the threat to a personal, tangible consequence, it remains abstract and easy to ignore. Without that context, it's challenging for people to feel the urgency or understand why cybersecurity matters beyond the realm of IT.
2. How can we effectively prioritize and implement cybersecurity practices?
Start with the fundamentals. It is essential to know where your data lives, what systems support it, and who has access. Then, focus on hygiene. Keep your systems patched, your endpoints secure, and your controls (such as network protection systems, identity management and access controls) properly configured. Most breaches don’t happen because of exotic threats; they happen because the basics were missed. Cybersecurity doesn’t need to be complex to be effective. It just needs to be intentional. And it’s not just IT’s job, it is everyone’s.
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3. What are three actions a CEO can take to protect their company from cyberattacks?
Create a culture that encourages security - A CEO must set the tone and make security part of the company’s DNA, from strategy to delivery, and include security at every step of the way.
Fund it like you mean it - Hire the right security leader who’ll drive security that works lock step with the business, give them real authority, and make sure they have a seat at the decision-making table.
Build for resilience - You can’t promise perfection, but you can prepare to recover fast. Ensure your business can withstand a setback and continue operating with minimal disruption.
4. What are the three best resources for learning more about cybersecurity?
If you are starting out, there are excellent resources, such as CISA.gov, Cybrary, and SANS, that cover the essentials in plain language. Additionally, numerous valuable videos and resources for self-paced learning are available from platforms such as Google, Microsoft, and Amazon Web Services.
For folks further along in the journey, there are podcasts like Risky Business and Darknet Diaries that you can lean on.
More importantly, engage in conversations with other practitioners. Exchanging real-world challenges and solutions is where real learning happens. Plan to attend conferences such as BSides, DEFCON, Black Hat, CCC, or their local chapters. Pro Tip: Most of the local chapters (linked to larger groups) are free, and local events are reasonably priced. It’s a great way to stay current and connected.
5. What is one piece of advice for those wanting to pursue a cybersecurity career?
I would say, “Stay curious.” That’s your superpower. And don't worry if you didn’t come from a traditional cybersecurity background. You will find your lane, and your past experience might just give you an edge.
I will add one more thing: Build your network. That’s one thing no one says enough. The people you meet will open doors, share their lived experiences, and help you grow and develop. Something no course or certification can teach you.
With great power comes great responsibility, like sharing this article. LOL
