From Senior Penetration Tester to Product Manager: Evolving from Breaking Systems to Building Them Securely


Introduction

For most of my career, I lived in a world of exploits, payloads, and red-team reports. I spent countless hours trying to break systems, uncover vulnerabilities, and simulate real-world attacks to help organizations strengthen their defenses.

Today, I found myself on the other side — building the very products that I used to test.

Transitioning from a Senior Security Consultant and Senior Penetration Tester to a Product Manager in the cybersecurity domain has been both exciting and humbling. It’s a shift from attacker mindset to builder, defensive mindset — and it has reshaped how I think about technology, people, and impact.

The Why: Moving Beyond Finding Flaws

Pen testing and consulting gave me a deep understanding of how systems fail — but after years in that role, I started asking myself a different question:

“What if I could influence how we design security from the very beginning?”

As a Product Manager, I now have that opportunity. Instead of identifying gaps after a product ships, I help shape security requirements before a single line of code is written. It’s not just about fixing vulnerabilities anymore; it’s about building secure, usable, and scalable products by design.

That shift in perspective has been one of the most rewarding parts of this journey.

The Mindset Shift: From Depth to Breadth

One of the biggest challenges in this transition was realizing that product management is not just technical — it’s multidisciplinary.

As a penetration tester, I lived deep in the details: network layers, exploit chains, encryption flaws, and patch management. As a Product Manager, my scope expanded to include:

  • Customer needs and user experience
  • Business strategy and market positioning
  • Engineering priorities and timelines
  • Compliance and certification requirements (like FIPS, FedRAMP, SOC 2)
  • And also advanced and innovative security protections

The challenge was learning to zoom out without losing depth — to translate complex technical risks into product decisions that make sense for the business and the customer.

Communication Is the New Superpower

In cybersecurity, precision is everything — a single misconfigured rule or unpatched system can have catastrophic consequences. But in product management, communication becomes just as critical as technical precision. The product manager sits at the intersection of customer discovery, company strategy, and R&D capabilities, translating complex security and performance considerations into meaningful product choices.

Every decision carries trade-offs — stronger security often comes with performance costs, compliance requirements can slow innovation, and customer demands may challenge technical limits. A great PM communicates these realities with context and clarity, turning complexity into understanding.

Ultimately, great cybersecurity product management is about storytelling grounded in strategy — explaining not just how something works, but why it matters, who it impacts, and how the team can move forward together.

Testing AI Systems: Lessons for Product Thinking

Before moving into product management, I had the opportunity to work closely with AI-driven applications — testing, evaluating, and identifying vulnerabilities in models and systems powered by machine learning.

That experience taught me an important lesson: AI systems are not magic — they’re code, data, and logic like any other system. They can be attacked, manipulated, or misunderstood if not designed securely.

Understanding the attack surface of AI applications gave me a broader appreciation for how modern products must be built — securely, transparently, and with resilience in mind.

Experience in AI-driven penetration testing guides my thinking around risk, data integrity, and product design, my experience in AI-driven penetration testing shapes how I approach risk, data integrity, and product design. These lessons help build the next generation of cybersecurity solutions — not just for protection, but also for smarter management, enhanced visibility, and real-time observability.

Lessons Learned (So Far)

  1. Your technical foundation is your biggest asset. It helps you make smarter product decisions and earn credibility with engineering teams.
  2. Security is never “done.” It must be embedded into every phase — from ideation to deployment.
  3. Empathy is essential. Understanding customer challenges and developer constraints is what turns security from a blocker into a value proposition.
  4. Stay curious. The security landscape evolves fast — AI, Kubernetes security, cloud compliance — and you must evolve with it.

Looking Ahead

Moving from penetration testing to product management has been a true transformation — from identifying individual risks to designing systems that reduce them at scale. The challenge is different, but no less exciting; in fact, it’s infinitely more impactful.

I chose Radware because of its unique position in the application security market. Radware combines AI-driven threat detection, automated mitigation, and deep expertise in application and network security, enabling organizations to protect their applications proactively without sacrificing performance. Being a PM here allows me to translate frontline security insights into products that deliver both resilience and innovation.

At Radware, we’re not just building defenses — we’re shaping the future of secure, high-performance digital experiences. Every decision, every feature, and every innovation is an opportunity to help organizations operate confidently, innovate faster, and stay ahead of evolving threats. This journey is about turning security expertise into products that empower and protect, at every layer.

Jitesh Sharma

Jitesh Sharma

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