How to Start a Conversation with a CISO

Insights and Key Takeaways

The Challenges of Connecting with CISOs

Insight: One of the biggest challenges for sales teams is simply starting a conversation with CISOs. The conversation is often met with skepticism and resistance due to the sheer volume of inbound messages CISOs receive daily. CISOs often mention feeling bombarded, which leads to frustration and disengagement from initial outreach attempts.

Sales teams often overlook the reality of a CISO’s workload and environment.

With constant security threats, resource constraints, and the pressure to protect their organization, CISOs have little time for generic sales pitches.

Instead, they look for meaningful conversations, which involve genuine interest, deep research, and authentic relationship-building.

The traditional approach of relentless email sequences, mass outreach, and cold calls is perceived as disruptive rather than helpful, making it vital for salespeople to adopt a more nuanced, relationship-centric approach.

Building Trust Through Community Engagement

Insight: Successful engagement with CISOs starts with building authentic relationships and becoming part of the cybersecurity community. CISOs appreciate sellers who genuinely contribute to the industry by sharing insights, supporting educational initiatives, and participating in community events, rather than just pushing products.

Instead of a transactional approach, successful sellers immerse themselves in the community.

This includes contributing to discussions, attending industry events, and engaging meaningfully on platforms like LinkedIn.

By demonstrating industry knowledge and empathy for the challenges CISOs face, salespeople can gradually earn trust and credibility, laying the foundation for future sales conversations.

It’s not just about getting the sale—it’s about creating long-term advocates and partners within the community.

The Power of Progress Over Product Pitches

Insight: CISOs are more interested in how a product will help them achieve specific goals and progress in their security program than in the product itself. The most valued conversations are those that center around solving problems and achieving business outcomes.

Sales teams need to pivot from product-centric conversations to ones focused on helping CISOs progress in their cybersecurity strategy.

It’s about identifying the CISO’s current maturity level, understanding their key objectives, and tailoring conversations to demonstrate how the solution aligns with their progress needs.

Sellers should position themselves as partners in achieving the CISO’s strategic goals, rather than simply pushing product features.

Integrity is Non-Negotiable in Sales Interactions

Insight: Integrity is a critical factor for CISOs when evaluating whether to engage further with a salesperson. CISOs want transparent, honest, and straightforward conversations that avoid exaggerated claims and focus on realistic outcomes.

Sellers must approach CISOs with honesty, even when discussing the limitations of their solutions.

Being upfront about potential gaps or challenges not only demonstrates integrity but also fosters trust.

Conversely, overstated claims and aggressive sales tactics erode credibility and can permanently damage relationships.

To maintain integrity, salespeople should personalize outreach based on genuine research and align discussions with the CISO’s priorities and constraints.

The Importance of Patience and Long-Term Engagement

Insight: Sales in the cybersecurity space require patience. Immediate transactions are rare, as CISOs typically have long buying cycles and are often in the process of evaluating multiple solutions over extended periods.

Sales teams must adapt to the longer sales cycles in cybersecurity by investing in consistent, long-term relationship-building.

This involves understanding the CISO’s current needs, providing ongoing support, and engaging regularly without pressuring for immediate decisions.

Building a "ground game" by maintaining presence and relevance over time ensures that sellers remain top-of-mind when CISOs are ready to make a purchase.

TL;DR

The reality is, connecting with CISOs isn’t about spamming their inbox or bombarding them with cold calls.

It’s about meaningful, long-term engagement rooted in trust, authenticity, and community.

If you want to win in cybersecurity, you need to shift from transactional thinking to relationship-driven growth.

The CISOs I spoke with were clear—if you’re not adding real value or showing genuine interest, you’ll be left in the spam folder.

So, take the time to do your homework, personalize your approach, and be ready to play the long game. Y

our success will come from patience, persistence, and positioning yourself as a trusted partner—not just another vendor.

Until next time,
Dani