The cybersecurity product sales process is broken, but it doesn’t have to be – Source: www.csoonline.com

If you’re a CISO, chances are your inbox is filled with pitches from vendors claiming to have developed the latest game-changer in cybersecurity. And if you’re a vendor, you know the challenges of getting through to CISOs, the gatekeepers of security and risk management.

It’s not that the intentions on either side are bad; CISOs need effective solutions and vendors genuinely want to help solve those challenges. But somewhere along the way, the process of connecting vendors and CISOs has become inefficient, awkward, and, at times, downright frustrating.

Having experienced these challenges firsthand, I wanted to dig deeper, to really understand the nuances of this broken process, I reached out to Kiel Hogan, a sales leader at Island.io, to get his perspective. Kiel highlighted a critical element that encapsulates why this process feels so dysfunctional: it’s a dilemma wrapped in a double bind, layered with paradox.

At its core, the vendor-buyer engagement is caught in a practical dilemma, a conflict between two legitimate needs. On one hand, buyers — CISOs like me — want vendors to deliver a tailored solution to their specific problems upfront. We don’t have time for generic pitches or irrelevant products.

On the other hand, vendors need meaningful engagement with buyers to understand those specific problems well enough to offer tailored solutions. This creates a natural tension: one party wants answers, and the other needs questions.

Vendors and cyber leaders face double-binds and paradoxes

Then there’s the double-bind component of this relationship. Both parties feel stuck in a situation where neither option is ideal. If vendors engage without presenting something immediately relevant, they risk losing the buyer’s interest. However, if they attempt to present a tailored solution without truly understanding the buyer’s needs, they often come off as generic or disconnected. It’s a lose-lose scenario that perpetuates frustration on both sides.

Finally, there’s the paradoxical element, which feels like a Catch-22: vendors need to engage deeply to understand buyers’ problems, but buyers expect that understanding to be demonstrated before engagement. It’s a circular dependency that makes breaking the cycle inherently difficult. Kiel’s framing of this challenge put into words what many of us — CISOs and vendors alike — have felt for years but struggled to articulate.

The problem goes even deeper when you consider how vendors and CISOs are typically matched. Too often, the first point of contact is a junior sales representative — an SDR or ADR — tasked with initiating conversations with senior executives. These reps are often armed with talking points but lack the depth of understanding to connect meaningfully with someone operating at a strategic level.

Meanwhile, the CISO is grappling with high-stakes responsibilities like mitigating risks, ensuring compliance, and aligning security strategies with business goals. It’s a mismatch in both experience and priorities, and it sets the tone for a relationship that feels misaligned from the start. Why is the most junior salesperson tasked with engaging the most senior security leader?

So how do we fix this? How do we break out of the cycle of generic pitches, missed connections, and mutual frustration? Kiel and I agree that the solution lies in rethinking the way vendors and CISOs connect.

Breaking the cycle of poor vendor-CISO relationships

First and foremost, both sides need to embrace empathy and candor as foundational principles. Vendors must approach every conversation with empathy, recognizing that engaging with sellers is often just 10 to 20% of a CISO’s time, while engaging with CISOs may represent 90% of a seller’s focus.

Sellers need to understand that CISOs juggle immense responsibilities and need conversations that are as value-packed and efficient as possible. Sellers who embed themselves in the security community take the time to understand nuanced challenges, and approach CISOs with genuine intent to help will stand out in the crowded marketplace.

Likewise, buyers need to appreciate that sellers are not just “pushing products” but are trying to do their job. Sellers play a critical role in keeping their organizations afloat, which directly ties to budgets and the sustainability of the products CISOs rely on. When approached with sincerity and candor, sellers will often go to great lengths to build business cases, fight for discounts, or secure additional resources for buyers. It’s a two-way street, and the more both sides approach each other as partners rather than adversaries, the more productive the engagement becomes.

Candor also has a critical role in improving vendor-buyer dynamics. Far too much posturing exists in these engagements, often creating unnecessary friction. While the origins of this dynamic are complex and rooted in cultural and structural issues, the best engagements I’ve had as a security leader are those where both parties cut to the chase. For example, a CISO might say, “We like your product and see value in XYZ areas. If we can agree on $XXX, I’ll push for a December purchase.”

Similarly, sellers should be upfront about their priorities, whether it’s pricing, timing, or implementation details. This level of transparency eliminates guesswork and sets the stage for a much smoother process.

Creating a cybersecurity-specific marketplace would help

One potential enabler of these principles is to create a marketplace specifically designed for the cybersecurity world — a neutral platform where vendors and buyers can find each other based on real compatibility. Imagine a space where CISOs could explore solutions on their own terms, guided by peer reviews, detailed use cases, and industry-specific contexts. Vendors, in turn, could showcase their offerings in a way that aligns with what CISOs are actively seeking, rather than guessing or relying on cold outreach.

This marketplace would go beyond just matchmaking. It could streamline the entire engagement process, from initial introductions to final agreements. For instance, it could incorporate tools for managing NDAs, proofs of concept, and master service agreements, making the path from discovery to decision as frictionless as possible. Vendors wouldn’t have to gamble on cold emails, and CISOs wouldn’t have to wade through irrelevant pitches. Instead, both sides could engage in a way that feels intentional and mutually beneficial.

Ultimately, the goal is to move from a fragmented, often adversarial process to one that feels collaborative and aligned. The current model of cyber sales isn’t serving anyone well, but it’s not beyond repair. By addressing the root causes of frustration — the mismatched priorities, misaligned incentives, and lack of trust — we can create a system that works for everyone.

In an industry built on principles of efficiency and security, our approach to sales and engagement should reflect those same values. It’s time for a refresh, and I’m optimistic that by working together, vendors and CISOs can create a better way forward.