What happens when cyber risk leaders stop speaking in acronyms and start telling stories? In this episode, host Jason Bradwell sits down with Jeffrey Wheatman, SVP of Cyber Risk Strategy at Black Kite and longtime cybersecurity evangelist, to talk about how to lead with problems, not products.

From decades advising CISOs at Gartner to launching the panel show Third Party, Jeff shares what he's learned about building trust, breaking down "terminal uniqueness," and why vendors need to collaborate on educating the market instead of competing. If you care about cutting through noise in a saturated market, this conversation is packed with insights you can actually use.

Jason and Jeff dive into why so many cybersecurity vendors fall into the trap of "terminal uniqueness" believing they're so different that they can't learn from anyone else. Jeff explains why this mindset kills effective marketing and how leading with the problem, not your product features, is the only way to break through.

They explore why CISOs won't talk to sales teams (hint: it's not personal, it's about trust) and why the cybersecurity industry desperately needs more collaboration. Jeff makes a compelling case that we're at war with ransomware networks, yet vendors refuse to talk to each other about how to educate buyers.

The conversation shifts to buyer awareness stages and where most marketing completely misses the mark. Jeff shares his framework for thinking about audiences beyond just problem-aware buyers, and why "hallway therapy" at conferences builds more trust than any keynote ever will.

Jason asks Jeff how he'd spend $100K to build an audience (not a campaign), and Jeff's answer revolves around creating spaces for real conversation, which is exactly what led him to launch Third Party, a panel show tackling cybersecurity topics with both strategic and tactical depth.

They wrap with Jeff's shoutouts to creators doing cyber content right and key takeaways for B2B marketers trying to build trust in technical markets.

Whether you're a security vendor struggling to differentiate, a CISO trying to communicate risk to the board, or a B2B marketer in any technical space, Jeff's insights on problem-first storytelling and building genuine community will transform how you think about reaching your audience. This isn't about more content, it's about better conversations.

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00:00 - Introduction: Cutting through cyber noise

01:30 - Jeff's journey from Gartner to Black Kite

04:00 - Terminal uniqueness: the "we're different" trap

07:00 - Lead with problems, not product features

09:30 - Why CISOs avoid sales conversations

13:00 - We're at war: Why vendors need to collaborate

17:30 - Buyer awareness stages marketers miss

20:00 - Why competitors won't talk (and should)

24:00 - Hallway therapy beats keynotes

27:00 - The $100K audience-building question

30:00 - Launching Third Party panel show

35:00 - Strategic + tactical content together

38:00 - Cybersecurity creators doing it right

42:00 - Key takeaways for B2B marketers

Connect with Jason Bradwell on LinkedIn

Connect with Jeffrey Wheatman on LinkedIn

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How to Talk Cyber Risk So People Actually Listen | Jeffrey Wheatman, Cybersecurity Strategist at Black Kite

Pipe Dream | A B2B Marketing Podcast