Roy Katmor | Crain's San Francisco

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Roy Katmor


Roy Katmor is co-founder and CEO of enSilo, a San Francisco–based cybersecurity startup that protects companies after a breach, which typically involves data consequences such as disruption or theft. enSilo employs 80 people and has offices in Israel and Singapore. Katmor has more than 15 years’ experience working with companies such as Akamai, where he ran security strategy, and Imperva, as the head of product management.

The Mistake:

I underestimated the nature of culture.

I used to let people run [with a project], but once they made a mistake I would look into the mistake, and if it happened again and again, I lost trust. In a losing trust situation, I would get more involved. If something didn’t work, I’d take over. That is not a good culture, and it does not empower people. It doesn’t define what is success and what is failure.

If somebody isn’t meeting expectations, it’s either because you hired the wrong person — [though] let’s assume you tried not to — or that you weren’t clear enough about the product you’re trying to build.

The definition of culture is that everyone understands the goal. That means everybody needs to know what problem you are solving. Everybody in the company, from the first developer to inside sales to support, needs to know what kind of a problem we are solving and how our product solves it. It all starts with the culture.

If you define a culture that’s not vague, and if you empower your employees, you’re on the way to success.

The Lesson:

If you define a culture that’s not vague, and if you empower your employees, you’re on the way to success.

Of course, the goal is to succeed, but on the way to success, you’re going to fail. Let people fail; just know how to measure it. Measurements need to be something you define upfront when you start a project. If an employee comes up with an idea that’s great, and you let them run with it, that’s part of empowering people. But you don’t want to get the middle of the process and [discover] no one’s sure whether it was a success or a failure because nobody defined it well enough.

Plan and manage with milestones to see whether goals were met or not in a way that’s visible so you can track it together and reach the decision: Are we succeeding? You need to make the call on whether you are or not. People [typically] don’t see failure as a way to succeed. But it’s not about failing; it’s about failing fast in order to succeed.

Roy Katmor is on Twitter: @RoyKatmor.

Photo courtesy of enSilo

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