CISOs don’t want your sales emails. They don’t care about your buzzwords. And they can sniff out polished nonsense faster than you can say “zero trust.”

In Episode 6 of Chocolate Pill, we sit down with Den Jones, Founder of 909Cyber (and former CISO at Adobe and Cisco), to ask the questions every cybersecurity marketer should be asking:

• How do CISOs actually want to be approached?
• What gets your message ignored—or gets you a meeting?
• How do you build trust with one of the hardest audiences in B2B?

Spoiler: It’s not about leading with AI. It’s not about adding more jargon. And it’s definitely not about sending them a 54-bullet list of features.

Highlights from the episode:

• Why CISOs ignore 95% of outreach—and what makes the 5% stand out
• Why zero trust, reduce risk, and ransomware don’t mean what you think they mean
• What CISOs want from marketing: authenticity, trust, and human connection
• How B2B marketers are shooting themselves in the foot by over-polishing their messaging
• The rise of physical mail and other creative ways to get a CISO’s attention
• Why engineers make up most CISOs—and why that changes how you market to them
• Why AI in security products triggers skepticism, not interest
• The #1 mistake startups make when trying to pitch CISOs
• Why a pragmatic approach to marketing (not perfect messaging) builds credibility and trust

One big takeaway:
If you want to market to CISOs, stop trying to sound impressive. Start trying to be useful. Build trust first, then sell. And remember: a little raw honesty beats a polished pitch every time.

👉 Listen in as Chris, Erin, Sandi, and Den break it all down.

‍

Lines We Couldn’t Stop Quoting

Den:

"If everything is perfect and polished, there’s no trust there. There’s no trust in being perfect and polished."

‍

Sandi:

"The CISO origin story is the engineer personality—just more money, a better suit, and more responsibility."

‍

Erin:

"Marketing and SEO are the dark arts. So is security. And in both cases, trust is everything."

‍

Chris:

"I view the CISO audience as the double black diamond of marketing. If you can market to CISOs and succeed, you’ve probably got something."

‍

Bonus:

"Don’t tell me how you made the sausage. Just tell me if it solves my problem." —Den, on why marketing doesn’t need to lead with AI.

‍

So what?

Marketing to CISOs isn’t about clever subject lines or shiny messaging. It’s about relevance, trust, and respect for their time and expertise. If your marketing playbook is full of buzzwords and feature dumps, it’s time to rethink it. Start with what they care about. Speak their language. And never forget: engineers can smell marketing BS from a mile away—and so can CISOs.

‍