From the outside, Upwind Security looks like it’s had a smooth journey so far. Just four years in, the cloud security startup is now worth $1.5 billion, and boasts the likes of Siemens, Peloton, Roku, Wix, Nextdoor and Nubank among its clientele. But if you ask the company’s co-founder and CEO Amiram Shachar, the journey to get here was anything but certain.

β€œThree years ago, we would spend hours asking ourselves if we were heading in the right direction, and 80% of the time, it felt like we weren’t,” a candid Shachar told TechCrunch in an interview following the startup’s recent $250 million Series B.

β€œAt the beginning, we constantly questioned whether the market needed our solution, whether it would be too hard to integrate into larger systems, or if customers would adopt it,” he recalled.

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