Hello to Canada’s SaaS Community,
At SAAS NORTH, one of the most talked-about sessions didn’t come from a notable name from the global tech and SaaS community. It came from a costumed figure in a SaaSquatch suit. The “Masked Investor,” disguised to preserve anonymity but empowered to speak with honesty, peeled back the curtain on what VCs really think about founders, funding, and the future of SaaS.
It was candid, occasionally brutal insight from someone who’s seen hundreds of founders’ pitch, scale, stumble, and pivot.
The session captured a feeling many in SaaS have sensed: the game has changed, and it’s time to get real.
Key takeaways:
- VC funding comes with tradeoffs. Founders often overlook the power shift and governance implications that follow a raise.
- SaaS models are being redefined by AI and economic pressure. Long-term contracts are out; outcome-based pricing is in.
- Communication is a differentiator. Regular updates—even to investors who passed—build trust, traction, and future opportunity.
Co-Founder/Producer, SAAS NORTH Conference Editor, SAAS NORTH NOW
Founders are often told to “think big,” “move fast,” and “raise money.” But what if the real challenge isn’t getting capital—it’s what comes after? In an industry shaped by hype cycles and funding headlines, it’s rare to hear the honest, hard truths about how venture capital actually works.
That’s what made “The Masked Investor” session at SAAS NORTH so refreshing (or was it the SaaSquatch outfit). Beneath the costume was a seasoned VC who’s spent a decade deploying hundreds of millions—and who was finally free to speak plainly about what founders are getting wrong.
Today, we unpack the essential lessons from that conversation—from how Canadian VC dynamics shape founder outcomes to why traditional SaaS models are giving way to a new era of pricing, and what it really means when a VC says “no.”
Keep reading for a rare, insider’s look at what venture capital looks like behind the mask.
Understanding the Canadian Capital Landscape
Canadian founders operate in a very different venture ecosystem than their U.S. counterparts. In Canada, many funds raised capital through government-backed programs like VCAP and VCCI . These funds come with mandates that extend beyond pure profit—like job creation and economic development.
This dynamic can lead to misalignment between what VCs want, what LPs need, and what founders expect.
For founders, this means knowing who you’re raising from and what drives their decision-making. It also means adjusting expectations—Canadian VC’s may move slower or favor different types of growth than Valley investors.
SaaS Isn’t Dead—But the Model Is Evolving
While some fear AI will cannibalize SaaS, the Masked Investor sees something more nuanced: evolution. Traditional SaaS models—particularly those locked into rigid pricing and long-term contracts—are losing favor. Buyers want outcomes, not subscriptions.
The investor predicted a shift toward “results-as-a-service” models, where companies charge based on what gets delivered—not what gets promised.
Founders need to rethink not just what they build, but how they deliver and monetize value. Chasing trends isn’t enough—building for depth and utility will separate winners from hype machines.
Raising Capital? Understand the Tradeoffs
One of the starkest realities the Masked Investor shared is how little founders often understand about the strings attached to venture capital. Taking VC money isn’t just a cash injection—it’s a shift in governance, accountability, and control.
VC-backed founders often face pressure from boards, audit committees, and investor expectations that don’t always align with long-term thinking. Bootstrapped founders, on the other hand, maintain autonomy—and in many cases, greater personal wealth.
The key is knowing what you want from your business and being brutally honest about whether venture funding supports that vision.
Communication Builds Confidence (Even If You Got a “No”)
One surprising insight was how much weight VCs place on communication. Even if they say no, the story isn’t over. Consistent, clear updates show investors that you can execute, adapt, and grow—even if they didn’t bet on you the first time.
Founders who stay quiet after a “no” often disappear. Founders who keep updating build a trail of progress that VCs can’t ignore—and might eventually reengage with.
The message from behind the mask was clear: substance beats spectacle. The founders who win in 2025 aren’t the ones with the flashiest decks or the biggest raises—they’re the ones who know how to build, communicate, and grow with intention.
Oh—and if we had to place bets on who was really behind the mask? Let’s just say… we wouldn’t be surprised if it was someone whose portfolio is already shaping the next decade of Canadian SaaS.
SAAS NORTH is THE Canadian hub for rapidly-scaling SaaS founders and their teams. Learn, network, and grow with Canada’s largest in-person SaaS community at SAAS NORTH.
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