Security | Threat Detection | Cyberattacks | DevSecOps | Compliance

Technical skill opens doors, but communication is what gets ideas accepted by leadership. In cybersecurity, the real challenge is often turning complex risk into clear business language that a CEO, CTO or CFO understands straight away.

Bad sales habits often come from low effort, low curiosity and people who stop learning once they land the role. When sales becomes lazy, every decent salesperson has to fight twice as hard to rebuild trust with buyers who are already tired of being spammed.

The biggest mistake is assuming persistence alone will win the deal. Repeating the same message and listing product features without understanding the real pain points makes the whole approach feel tone deaf from the start.

Nothing kills trust faster than pitching services to someone who already does that work for a living. If your outreach is auto generated, poorly targeted and built on zero research, most CISOs will write you off before you ever get a second chance.

Desperate sales outreach rarely works because it feels generic and self serving from the first line. A better approach starts with real research, a relevant human detail and a message that proves you paid attention before trying to earn the conversation.

Why do so many vendors still get it wrong when selling to security leaders? Welcome to Razorwire, the podcast where we share our take on the world of cybersecurity with direct, practical advice for professionals and business owners alike. I’m Jim and in this episode, I’m joined by Marius Poskus, CISO at a fintech organisation and host of the Cyber Diaries podcast, and Simon Woods, co-founder of One Compliance and a salesperson who’s been working in cybersecurity sales for over 15 years.

This episode breaks down why so many sales approaches fail with CISOs, from lazy research and scripted persistence to tone deaf messaging and zero trust building. It also shows what works better, active listening, free value, real relationships and outreach that respects how security leaders think and buy.

Not every undisclosed bug is undiscovered; some are quietly sold through brokers to whoever pays the most. Governments, criminal groups and private buyers all compete in a shadow market where valuable software flaws become products long before the public ever hears about them.

The deepest threat is not that AI finds one clever bug, it is that it can do offensive work at a scale humans never could. Tasks that once demanded time, money and elite skill can now be accelerated, repeated and widened far beyond the limits of a traditional red team.

The next phase of cyber conflict may not be human against human, but attacking agents against defending agents at machine speed. Offensive models will probe, adapt and retry, while defensive models learn to counter them, leaving humans to supervise a battle fought mostly by software.