Behind the Scenes with Jon Sadler, COO of Cloudality

I recently sat down with Jon Sadler, Cloudality’s COO and co-founder, for a conversation that turned out to be as insightful as it was human.

Jon admitted that stepping into the COO role has been full of surprises. As a founder, he’s worn countless hats, but what stood out most wasn’t the workload, it was the unexpected generosity of the community. “People are willing to share advice without asking for anything in return,” he said with genuine appreciation.

When we got into lessons learned, Jon’s advice was refreshingly candid: mistakes are unavoidable, and that’s okay. What matters is how you recover and move forward. “Don’t let errors paralyze you,” he explained. “Trust your instincts, make the call, and keep going.”

We also talked shop. While many COOs live and die by standard metrics, Jon confessed his real obsession is efficiency at the crossroads of technology and operations. He lights up when describing small, often invisible gains that make teams faster and workflows smoother.

Of course, not everything was serious. When I asked Jon to imagine Cloudality as a restaurant, he pictured a family-style dining experience: communal, warm, and focused on connection. He even shared a story about eating with his hands in a Nigerian restaurant, where the act of sharing food made the experience unforgettable.

What struck me most in our chat was Jon’s balance. He can dive deep into the technical details, switch to big-picture business strategy, and still stay calm through it all: a calmness he credits to meditation and yoga.

Behind the title of COO, Jon comes across as someone who is equal parts strategist, operator, and connector. Our conversation left me not only with leadership lessons, but also a stronger sense of the values shaping Cloudality’s culture.