From Satellite Dishes to a $26 Billion Valuation: The Unlikely Rise of Damien Singh
The former Canva CFO's path from dropping out of university to leading one of the world's most valuable private technology companies is anything but conventional.
There are careers that follow a plan, and then there are careers that follow something harder to name. For Damien Singh, the former CFO of Canva, the journey began not in a boardroom but on a rooftop, installing satellite TV dishes after dropping out of university at nineteen.
That chapter didn't last long. Staring at the gap between where he was and where he believed he could be, Singh asked himself a question that would redirect the course of his life: "What are you doing with your life?" The answer, it turned out, was accountancy.
He landed a role at a small firm in Bristol, qualified as a Chartered Accountant in four years — a process that typically takes six — and built a career in audit. By his mid-twenties he was a Senior Manager at a mid-tier Sydney firm, on a clear path to partnership. He turned it down.
The Pivot That Changed Everything
Instead of the partnership track, Singh took a pay cut to join an eight-person technology startup. The experience was a crash course in what it actually takes to build a business: finance, operations, fundraising, and the kind of problem-solving that no professional qualification fully prepares you for. When that startup wound down after about a year, he found his next role on a jobs board: Assistant Financial Controller at Canva.
He joined in June 2016. Within months, the CFO departed. Singh stepped into the finance lead role and eventually became CFO — a title he would hold for eight years during one of the most remarkable growth stories in Australian corporate history.
Eight Years Inside Hypergrowth
The numbers are genuinely striking. Under Singh's tenure as CFO, Canva grew from roughly US$10 million in annual revenue to more than US$2 billion, while maintaining free cash flow profitability throughout. The workforce expanded from around 50 employees to more than 4,000 globally. The company's valuation climbed from US$100 million when he joined to US$1 billion in 2018, and ultimately reached US$26 billion following a US$1 billion-plus capital raise in late 2023 — a process Singh led, involving a US investor roadshow and collaboration with major global investment banks.
"That kind of exposure to hypergrowth — across finance, operations, investor relations and strategy — is something very few people experience, particularly in Australia," Singh has said. The experience earned him the Australian CFO of the Year Award in 2023 and a speaking slot at the Morgan Stanley Annual Spark Conference.
What Comes After the Defining Chapter
For eight years, Singh's identity was closely tied to being the CFO of Canva. Stepping away from that role meant letting go of more than a title — it meant rediscovering who he was without it. That process, he says, ultimately pushed him toward something more grounded than the conventional next step.
Today, through his work as an early-stage investor and strategic advisor, Singh is focused on helping build and support organisations that create enduring value for the people and communities they serve. He has already started deploying capital into pre-seed and seed-stage technology companies, including an early investment in Adora — an AI-native product mapping platform founded by former Canva operators — which has since raised a US$7 million Seed round led by Blackbird Ventures.
He has also become the owner of Gwalia United FC, formerly Cardiff City Ladies, applying the same long-term thinking to women's football — a sector he sees as still in the early stages of professionalisation.
The arc from satellite dishes to a $26 billion valuation is not a story about luck. It is a story about the compounding effect of disciplined decisions, made consistently, over a very long time — and about what becomes possible when someone refuses to accept that the path they're on is the only one available to them.
