The Team Is the Moat

At our inaugural AGM in San Francisco in September 2026, Amiram Shachar, Upwind's co-founder and CEO, told a story. A journalist visiting Upwind’s HQ heard cheering from a nearby room and asked, “Who’s leaving?”

“No one,” Amiram said. The cheering was for dozens of employees marking ten years of working together, across two companies.

The first was Spot.io, which cut companies’ cloud computing bills by running their workloads on spare capacity. Amiram co-founded it and sold it to NetApp for $450 million in 2020. When he started Upwind four years ago, he went straight back to that team. Fifty of them had rejoined him by the end of the first week, and Upwind has grown to more than 600 people since.

Today they’re building a cloud security platform around runtime, covering posture, vulnerability management, and real-time threat detection. Rehiring a whole team at once is contrarian, but it’s working. Upwind has raised more than $430 million, revenue grew 4x in 2025, and it’s on track to more than triple in 2026. Penny Jar has been with Amiram since the seed.

On stage at the AGM, he sat down with Jonathan Davidson, former EVP and GM of Cisco Networking, to talk about scaling in the AI era. Jonathan is a member of the Penny Jar Collective, the senior operators and executives who support our founders. The takeaways:

Hire for endurance. Find people ready to run with you for two decades. Short stints won’t cut it, no matter how impressive. Look for curiosity and judgment that show up as tenure, like multiple promotions at one company. Jonathan would know: he joined Cisco as a support engineer in 1995 and, two stints later, left in 2024 running its $30 billion networking business.

Find your 10 percent. AI widens the gap between average and exceptional. Company-wide adoption is nice, but the outsized returns come from the top ten percent of your product and engineering team pushing it hardest.

Make it viral. When your power users crack something, replicate it and scale it. Find the best people using AI the best way, then repeat, repeat, repeat.

Upwind’s edge isn’t the tools. It’s the people who stuck around to build them.