Damien Singh’s path from CFO of Canva to early-stage investor is built on a simple premise: most founders don’t have access to the kind of experience that actually helps.
The gap between raising a first round of capital and building a company that actually works is larger than most investors acknowledge. Damien Singh is trying to help founders close it.
Singh served as CFO of Canva for eight years, during a period when the company grew from roughly US$10 million in annual revenue to more than US$2 billion. He scaled teams from 50 to more than 4,000 people, managed operations across multiple international markets, led the financial and operational oversight of multiple strategic global acquisitions, and built relationships with many of the world’s leading venture and growth investors.
Now, through early-stage investing and strategic advisory work, he is bringing that experience to bear at the earliest stages of a founder’s journey.
The Gap He’s Trying to Bridge
“What I realised after stepping away from that role is that many founders — especially those building early-stage companies — simply don’t have access to that kind of experience or guidance,” Singh says. “The gap between the very early bootstrapped phase of a company and the point where venture capital becomes available can be particularly challenging.”
The companies Singh focuses on are typically at the pre-seed or seed stage. They are often led by technical or product-oriented founders with strong ideas but limited experience navigating the operational realities of scaling: building scalable financial systems, structuring early teams, preparing for fundraising, balancing product development with commercial growth.
Those are precisely the problems Singh spent nearly a decade solving at Canva. His support comes not from theoretical frameworks but from having lived through the journey himself — including the decisions that turned out to be wrong.
A Portfolio With Early Signal
Singh has already started deploying capital. One of his early investments was in Adora, an AI-native product mapping platform founded by former Canva operators. The company has since raised a US$7 million Seed round led by Blackbird Ventures at a valuation of approximately US$35 million, with participation from Skip Capital, Designer Fund and other investors.
He has also participated in the Athletic Ventures Champions Fund, connecting him to a global network of professional athletes actively involved in backing technology companies. Beyond technology investing, Singh owns Gwalia United FC — formerly Cardiff City Ladies — which he is building as a commercially sustainable football organisation, applying the same long-term financial discipline that characterised Canva’s growth.
What He Is Looking For
Singh’s criteria for the founders he chooses to support reflect both his professional experience and his personal values. “The founders I work with tend to be ambitious, thoughtful and focused on building something meaningful over the long term,” he says. “Those qualities are far more important than credentials alone.”
The best teams, in his view, are built around people who combine strong capability with humility, curiosity, and a willingness to keep learning. That standard applies as much to the founders he backs as to the teams those founders assemble.
“The goal is to support a small number of ambitious companies over time and help them grow into organisations that create lasting value,” Singh says. “Not just provide advice, but help founders build organisations that are financially sustainable and designed to endure.”
In an investing landscape full of capital competing for the same deals, the differentiator Singh is offering is something harder to manufacture: direct experience, applied early, from someone who has actually been through the journey.
