Hyperproof’s Playbook: How to Build Trust with Enterprise CISOs When You’re the New Kid on the Block

Breaking into enterprise sales is challenging enough. Breaking in as a startup in the hyper-competitive security and compliance space? That’s a whole different game. Yet Hyperproof managed to do exactly that, growing “at least two x a year for a number of years” while building a customer base of “hundreds of customers, dozens of partners.”

In a recent Category Visionaries episode, Hyperproof CEO Craig Unger shared the unconventional strategies that helped them gain traction with enterprise CISOs. Here’s their playbook for building credibility in a crowded market.

Reframe the Problem While most compliance vendors focused on passing audits, Hyperproof identified a deeper problem. As Craig explains, “The way you really need to ensure your compliance is by having all hands on deck and making sure that everybody can play a role and that the software itself supports the contribution of anybody who has something to contribute.”

This insight came from Craig’s own experience at Microsoft, where he faced potential fines of “a million dollars user a day” with “100 million unique users” during a critical FTC audit. The experience showed him that traditional approaches to compliance weren’t working.

Target the Right Decision Maker Rather than selling to traditional compliance or legal teams, Hyperproof deliberately targeted CISOs. “About 75, 80% of the time we sell into the CISO,” Craig notes. “We might start with the CISO and they’ll route to the compliance manager or chief compliance officer or somebody with a compliance title.”

This wasn’t just a random choice. Craig recognized that “a lot of compliance used to be done out of legal. We have some customers that are also in the legal department, but a lot of the tech compliance has migrated away over to the CISO team.”

Rethink Analyst Relations Instead of pursuing expensive relationships with major analyst firms, Hyperproof took a more targeted approach. Craig explains, “When you’re a smaller company, it’s more beneficial to build relationships with smaller analysts, folks who work individually, they tend to have more unique viewpoints and they can kind of bring you into more unique situations.”

They focused their analyst budget on high-impact events: “What we tend to do with our analyst dollars instead is go to events because some of the events for B2B could be super helpful. I mean, I’ll call out the Gartner Conference, we go there, it’s actually real helpful.”

Position Against Market Evolution Hyperproof positioned itself as part of a broader evolution in how organizations handle compliance. Craig draws parallels to security’s evolution: “Compliance is following the historical track of security where it started. Also as a small group of people, they may do penetration tests and send reports to the board and then you think your organization is secure.”

This positioning resonated with CISOs who had lived through security’s transformation from a specialized function to an organization-wide responsibility.

Build Trust Through Transparency Perhaps most importantly, Hyperproof challenged traditional assumptions about trust. “The compliance and security world hasn’t really adjusted to that. In other words, they’re still laboring under the belief that in order to do well in the market, everybody that they serve needs to be convinced that they’re perfect and they don’t make mistakes.”

Instead, they advocated for “the normalization of and now is the likelihood of human error that’s going to happen, but it allows them to kind of build trust in those situations where it’s kind of most tense because a mistake might have been made.”

For B2B founders trying to break into enterprise sales, Hyperproof’s experience offers valuable lessons. Success isn’t just about having the right product—it’s about fundamentally reframing the problem, targeting the right decision makers, and building credibility through unconventional channels. Sometimes, being the new kid on the block can be an advantage—if you’re willing to challenge established assumptions and offer a fresh perspective on old problems.