Every year, CloudNY brings together 150 CEOs from the cloud ecosystem to learn from Founders & CEOs who have built and scaled billion-dollar technology companies from the private and public ecosystem.

This year, we heard from the iconic entrepreneurs behind Cloudflare, Shopify, Upwork, ZoomInfo, and Wix, and it quickly became clear that the best companies don’t just scale — they rethink how scaling should happen. They evolve faster than the world around them. And they make bold calls long before the market gives them permission.

Since off-the-record conversations are generally the most valuable, we have kept Chatham House Rules in place for CloudNY and the specific information shared during the summit. That said, we have summarized a few select company-building lessons from CloudNY below, in the hopes that they will be helpful for Founders who could not attend but are looking to learn from those who have been where they are before.

Reinvention Isn’t Optional. It’s Survival.

Every leader at CloudNY hammered home the same truth: reinvention isn’t a pivot — it’s a permanent muscle. Matthew Prince, CEO of Cloudflare, put it bluntly: “Culture isn’t something you preserve. It’s something you evolve.” It was a sentiment echoed across the board. Hayden Brown described how she led Upwork through a full re-founding—both product and cultural—in response to the rise of AI, refusing to let the company wait for permission to change. Meanwhile, Avishai Abrahami of Wix warned that because of AI, companies need to assume their tech stack will be obsolete in five years and start rebuilding now. These leaders weren’t just talking about incremental updates; they’re operating with a sense of urgency that treats reinvention as the default, not the exception.

Builders Win. Bureaucrats Lose.

One of the clearest throughlines of the event was the primacy of builders. Shopify’s Harley Finkelstein emphasized the importance of “spiky” talent — people who are exceptionally good at one thing rather than generalists polished by corporate conformity. Avishai Abrahami shared how at Wix, developers are empowered to think like builders, not just task-takers: “Velocity and quality improve when engineers think like builders, not task-takers.” Hayden Brown reinforced the theme, explaining that Upwork aggressively screens for builder mentalities when hiring new executives, specifically avoiding candidates who only know how to operate existing systems. Across every conversation, the message was clear: you can’t outsource creativity. You have to hire for it, nurture it, and empower it relentlessly.

Culture Can Be a Weapon Or A Weakness.

Culture isn’t a luxury—it’s the operating system of a company. Henry Schuck of ZoomInfo made that clear when he told his team after their IPO, “We’re building a Yankees or Red Sox. Not a Pittsburgh Pirates.” Championship culture, he explained, demands full discretionary effort and self-selection. Matthew Prince described how Cloudflare achieves radical transparency by sharing full board decks with the entire company, no redactions, no exceptions. And Hayden Brown made a stark point: “A tech reset without a culture reset fails.” Culture was framed not as a perk but as a necessity for execution, velocity, and resilience. Companies either weaponize it or get dragged down by it.

Scale Without Discipline is a Mirage.

Finally, we heard a lot (in strikingly honest fashion) about the dark side of growth. Scaling introduces complexity, misalignment, and technical debt—and it punishes companies that lose discipline. Henry Schuck described how ZoomInfo overhauled their executive operating practices with a radical change: one-hour ELT meetings every single day..no side meetings, no politics. Harley Finkelstein shared how Shopify built “Shopify OS” to track resourcing, drift, and alignment in real time, treating the company itself like a codebase. Avishai Abrahami warned that technical debt doesn’t just slow you down—“It kills your ability to compete when you finally have product-market fit.” Scaling up isn’t the goal. Scaling smart is. And that sentiment echoed across every single session at CloudNY.

Reflecting On An Incredible Day.

This year’s CloudNY summit was particularly powerful, not only because of the caliber of the speakers, but because we are at such a critical inflection point as AI reshapes the entire world around us. Within that paradigm, the CEOs we heard from are not only continuing to scale their companies, they’re building movements. They’re playing the long game — betting on reinvention, on spiky talent, on ruthless culture, and on operational excellence. And if CloudNY 2025 made anything clear, it’s this: The companies that endure don’t adapt when they have to. They adapt before they have to.

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CloudNY 2025 was a truly incredible day, and we’re grateful to our partners at Battery Ventures, to our sponsors at Golub Capital, Cooley, AWS, Comerica Bank, and Qatalyst, and to the 150 CEOs who spent the day learning with us.