{"id":2300,"date":"2025-03-12T06:00:00","date_gmt":"2025-03-12T06:00:00","guid":{"rendered":"https:\/\/cybersecurityinfocus.com\/?p=2300"},"modified":"2025-03-12T06:00:00","modified_gmt":"2025-03-12T06:00:00","slug":"the-cybersecurity-product-sales-process-is-broken-but-it-doesnt-have-to-be","status":"publish","type":"post","link":"https:\/\/cybersecurityinfocus.com\/?p=2300","title":{"rendered":"The cybersecurity product sales process is broken, but it doesn\u2019t have to be"},"content":{"rendered":"
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If you\u2019re 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\u2019re a vendor, you know the challenges of getting through to CISOs, the gatekeepers of security and risk management.<\/p>\n

It\u2019s 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.<\/p>\n

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>, a sales leader at Island.io<\/a>, to get his perspective. Kiel highlighted a critical element that encapsulates why this process feels so dysfunctional: it\u2019s a dilemma wrapped in a double bind, layered with paradox.<\/p>\n

At its core, the vendor-buyer engagement is caught in a practical dilemma, a conflict between two legitimate needs. On one hand, buyers \u2014 CISOs like me \u2014 want vendors to deliver a tailored solution to their specific problems upfront. We don\u2019t have time for generic pitches or irrelevant products.<\/p>\n

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.<\/p>\n

Vendors and cyber leaders face double-binds and paradoxes<\/h2>\n

Then there\u2019s the double-bind component of this relationship<\/a>. 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\u2019s interest. However, if they attempt to present a tailored solution without truly understanding the buyer\u2019s needs, they often come off as generic or disconnected. It\u2019s a lose-lose scenario that perpetuates frustration on both sides.<\/p>\n

Finally, there\u2019s the paradoxical element, which feels like a Catch-22: vendors need to engage deeply to understand buyers\u2019 problems, but buyers expect that understanding to be demonstrated before engagement. It\u2019s a circular dependency that makes breaking the cycle inherently difficult. Kiel\u2019s framing of this challenge put into words what many of us \u2014 CISOs and vendors alike \u2014 have felt for years but struggled to articulate.<\/p>\n

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 \u2014 an SDR or ADR \u2014 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.<\/p>\n

Meanwhile, the CISO is grappling with high-stakes responsibilities like mitigating risks, ensuring compliance, and aligning security strategies with business goals. It\u2019s 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?<\/p>\n

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.<\/p>\n

Breaking the cycle of poor vendor-CISO relationships<\/h2>\n

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\u2019s time, while engaging with CISOs may represent 90% of a seller\u2019s focus.<\/p>\n

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.<\/p>\n

Likewise, buyers need to appreciate that sellers are not just \u201cpushing products\u201d 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\u2019s a two-way street, and the more both sides approach each other as partners rather than adversaries, the more productive the engagement becomes.<\/p>\n

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\u2019ve had as a security leader are those where both parties cut to the chase. For example, a CISO might say, \u201cWe like your product and see value in XYZ areas. If we can agree on $XXX, I\u2019ll push for a December purchase.\u201d<\/p>\n

Similarly, sellers should be upfront about their priorities, whether it\u2019s pricing, timing, or implementation details. This level of transparency eliminates guesswork and sets the stage for a much smoother process.<\/p>\n

Creating a cybersecurity-specific marketplace would help<\/h2>\n

One potential enabler of these principles is to create a marketplace specifically designed for the cybersecurity world \u2014 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.<\/p>\n

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\u2019t have to gamble on cold emails, and CISOs wouldn\u2019t have to wade through irrelevant pitches. Instead, both sides could engage in a way that feels intentional and mutually beneficial.<\/p>\n

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\u2019t serving anyone well, but it\u2019s not beyond repair. By addressing the root causes of frustration \u2014 the mismatched priorities, misaligned incentives, and lack of trust \u2014 we can create a system that works for everyone.<\/p>\n

In an industry built on principles of efficiency and security, our approach to sales and engagement should reflect those same values. It\u2019s time for a refresh, and I\u2019m optimistic that by working together, vendors and CISOs can create a better way forward.<\/p>\n<\/div>\n<\/div>\n<\/div>\n<\/div>","protected":false},"excerpt":{"rendered":"

If you\u2019re 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\u2019re a vendor, you know the challenges of getting through to CISOs, the gatekeepers of security and risk management. It\u2019s not that the intentions on either side are bad; CISOs […]<\/p>\n","protected":false},"author":0,"featured_media":2280,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[3],"tags":[],"class_list":["post-2300","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-education"],"_links":{"self":[{"href":"https:\/\/cybersecurityinfocus.com\/index.php?rest_route=\/wp\/v2\/posts\/2300"}],"collection":[{"href":"https:\/\/cybersecurityinfocus.com\/index.php?rest_route=\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/cybersecurityinfocus.com\/index.php?rest_route=\/wp\/v2\/types\/post"}],"replies":[{"embeddable":true,"href":"https:\/\/cybersecurityinfocus.com\/index.php?rest_route=%2Fwp%2Fv2%2Fcomments&post=2300"}],"version-history":[{"count":0,"href":"https:\/\/cybersecurityinfocus.com\/index.php?rest_route=\/wp\/v2\/posts\/2300\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/cybersecurityinfocus.com\/index.php?rest_route=\/wp\/v2\/media\/2280"}],"wp:attachment":[{"href":"https:\/\/cybersecurityinfocus.com\/index.php?rest_route=%2Fwp%2Fv2%2Fmedia&parent=2300"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/cybersecurityinfocus.com\/index.php?rest_route=%2Fwp%2Fv2%2Fcategories&post=2300"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/cybersecurityinfocus.com\/index.php?rest_route=%2Fwp%2Fv2%2Ftags&post=2300"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}