Most people who spend eight years at the centre of a hypergrowth technology company leave with stories about the pace. The decisions made at speed, the teams assembled overnight, the systems scrambled together to keep up with a business doubling year after year.
Damien Singh has those stories. But the ones that seem to stick most are the ones about what almost didn’t hold together — and what it took to make sure it did.
Singh served as CFO of Canva from 2016 to 2024, during a period when the company’s annual revenue grew from roughly US$10 million to more than US$2 billion and its workforce expanded from around 50 employees to more than 4,000 across multiple international markets. He oversaw the company’s financial strategy, led multiple international acquisitions, managed investor relations with some of the world’s leading venture and growth funds, and ultimately guided a US$1 billion-plus capital raise at a US$26 billion valuation — a process that involved a US investor roadshow and collaboration with major global investment banks.
The Infrastructure Problem
The challenge that defined most of Singh’s tenure wasn’t finding growth — Canva had product-market fit and a compounding user base. The challenge was building the infrastructure to sustain it.
“Building systems that survive pressure, making disciplined financial decisions, and adapting the company as it becomes far larger than its early form” — those were the operational priorities that occupied most of his attention. Teams that worked at one scale stopped working at the next. Processes that served fifty people became bottlenecks at five hundred.
The companies that successfully navigate those transitions, Singh argues, are the ones that invest early in operational foundations rather than treating infrastructure as something to be solved later. “The most resilient businesses are the ones that maintain strong financial discipline and focus on building products that genuinely solve problems for customers,” he says.
Free Cash Flow as a Discipline
One of the most often-cited facts about Canva’s growth is that it maintained free cash flow profitability throughout its hypergrowth phase — a genuinely unusual achievement for a software company scaling at that rate. Singh regards that discipline not as a constraint but as a strategic advantage.
Companies that grow without financial discipline tend to become dependent on external capital to fund their operations. That dependency creates fragility. When market conditions shift or funding rounds become harder to close, businesses without strong fundamentals struggle. Businesses with them tend to endure.
The Next Chapter
Since stepping away from the CFO role, Singh has been applying those lessons at the earliest stages of a founder’s journey. Through early-stage investing and advisory work, he is focused on helping build and support organisations that create enduring value for the people and communities they serve.
His portfolio already includes Adora — an AI-native product mapping platform backed by Blackbird Ventures — and participation in the Athletic Ventures Champions Fund. He also owns Gwalia United FC, where he is testing the same financial discipline and long-term thinking in the context of women’s professional football.
“What I’m trying to do now is help bridge the gap between the very early bootstrapped phase of a company and the point where venture capital becomes available,” Singh says. “That gap can be particularly challenging, and many founders simply don’t have access to that kind of experience or guidance.”
He is not interested in offering theoretical frameworks. What he is offering is something harder to come by: the direct experience of having navigated a company through the full arc of hypergrowth — and having kept it together in the process.
