Why to Use the Compliance Framework in Your Messaging & Positioning

Who is Gary Hayslip?

Gary Hayslip is a seasoned cybersecurity executive with over 25 years of experience in information technology, security leadership, and risk management.

He currently serves as the Chief Information Security Officer (CISO) for SoftBank Investment Advisers, where he oversees enterprise cyber-security strategy and advises executive leadership on protecting critical information resources.

Throughout his career, Gary has held multiple high-level positions, including CISO, CIO, Deputy Director of IT, and Chief Privacy Officer roles for organizations such as the U.S. Navy, the City of San Diego, and Webroot Software.

His expertise spans architecting security programs, auditing large networks, and consolidating legacy infrastructures into virtualized datacenters.

A prolific author and thought leader, Hayslip has co-authored several influential books in the cybersecurity field, including "The CISO Desk Reference Guide" and "The Essential Guide to Cybersecurity for SMBs."

He is also an active member of professional organizations like ISC2, ISSA, ISACA, and Infragard, and serves on advisory boards for companies such as Cybereason, Box, and ProofPoint.

Gary holds several professional certifications, including CISSP, CISA, and CRISC.

He earned his BS in Information Systems Management from the University of Maryland University College and an MBA from San Diego State University.

Known for his ability to communicate complex security concepts to diverse audiences, Gary is a frequent speaker at industry conferences and contributes to the Forbes Technology Council.

Pro Tip for Connecting with Gary

If you want to connect with Gary, be honest and clear about how your solution aligns with compliance needs and business value.

And skip the buzzwords—Gary’s all about practical, tangible outcomes.

Oh, and be sure not to show up drunk or high to meetings with you.

(Yes, you read that right!)

Insights and Key Takeaways

Compliance Matters More Than You Think

Insight: CISOs are bound by compliance frameworks as much as they are by offensive security measures. For many, compliance is non-negotiable.

When marketing to CISOs, positioning your product as part of a compliance framework is crucial. Many vendors focus solely on offensive capabilities—AI, ML, blockchain—while overlooking compliance.

But for CISOs like Gary Hayslip, compliance isn’t just an add-on; it’s the reality they live in daily.

This means your messaging should prioritize how your solution aligns with specific regulatory requirements and provides seamless compliance integration.

Business Value Over Buzzwords

Insight: Buzzwords like "AI" and "blockchain" have become background noise to CISOs. What they want is practical solutions.

Gary is clear about his frustration:

For CISOs, it's not about which tech stack has more bells and whistles; it’s about tangible outcomes.

Marketers should focus on specific use cases, showing how their solutions directly impact business processes, reduce risks, and generate value.

Dropping jargon won’t resonate—solving problems will.

Integration is Key to a CISO’s Stack

Insight: When evaluating a new security tool, CISOs like Gary prioritize seamless integration into their existing tech stack.

Gary outlined a clear decision criterion:

The ease of integration determines the likelihood of adoption, not just for CISOs but for their teams.

A smooth integration path can make or break a deal. Emphasizing how your product fits into their ecosystem can be a major differentiator.

Avoid overcomplicating integration details and focus on how your solution adds to the existing infrastructure without disruption.

Transparency in Pricing Wins Trust

Insight: Overcomplicated pricing models create friction in the buying process. Simple, predictable pricing helps build trust.

Gary’s perspective is straightforward:

CISOs need to budget confidently, and pricing surprises can break deals.

Vendors need to be upfront about costs early in discussions to establish trust and set realistic expectations.

If your product is likely to cause unexpected costs, address them clearly instead of hiding them.

Personal Relationships Still Matter

Insight: Building trust through honest, personal conversations can lead to lasting relationships—even if a deal isn’t immediately closed.

Gary described his best vendor experience as one where the sales rep was honest about limitations, which led to Gary referring the vendor to three other CISOs.

Authentic conversations—focused on business problems, not just features—lay the groundwork for long-term relationships.

Tl;DR

As CISOs like Gary have made clear, the path to their approval is paved with trust, transparency, and relevance.

It’s not about throwing the most features at them but understanding their specific business contexts, compliance needs, and tech stack challenges.

Too many marketers get caught up in flashy features, complicated pricing, and aggressive tactics that leave CISOs skeptical.

If you really want to earn their trust, shift from selling to solving.

Until next time,
Dani