Startups must show rapid, low-effort value to eliminate enterprise buyer risk
Dean Sysman · They failed every POC—then grew their cybersecurity platform to $100M ARR in 5 years. | Dean Sysm... · PMF Show · Oct 16, 2025 · at 21:03
Dean Sysman, co-founder and CEO of cybersecurity company Axonius, explains enterprise buyer psychology and why fast time-to-value eliminates personal career risk for corporate decision-makers.
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“The thing that people don't understand, this is even truer, the bigger enterprise sales you go, the more this is true, is that companies have budgets, they have resources, and they will put those into buying products But only if they can trust the outcome. This is, again, like, the word trust here is the most important because when an organization buys, this is what we talked about before, it's people betting their careers on that decision being successful for them. There's this saying, ah, nobody got fired for buying from IBM, now that's not true anymore, right? What that saying means, and it's that trust factor, like, when you're talking to a VP or C-level person, you want them to put budget Into your product. What you need to make them feel is that there's a minimum of risk of them ending up looking like they made a mistake, right? And the more you can guarantee to them that will make them look good. That will make them see the value for their organization. They're going to bet heavily on you, right? People want to buy products. People want to create value for their company. They just don't want to waste or make mistakes, right? And if you can show value very quickly with very little effort, you've already done that, right?”
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