7 Go-To-Market Lessons from Canopy’s Journey to B2B Dominance

Most founders won’t tell you about the self-serve experiment that attracted Stanford kids in dorm rooms instead of enterprise buyers. Or the decision to eliminate over half their sales pipeline. In a recent episode of Category Visionaries, Matt Bivons, CEO of Canopy, shared the unfiltered reality of finding go-to-market fit in B2B enterprise software—including the spectacular failures that eventually led to massive growth.

Lesson 1: Not Every Product Should Be Self-Service

The PLG movement convinced many founders that self-service is always better than high-touch sales. Canopy learned otherwise. “The other piece that I spectacularly failed at was trying to do a self serve lending as a service,” Matt admits. The company built a freemium model with per-API pricing, following the Twilio playbook.

The experiment failed for two critical reasons. First, it attracted the wrong customers: “So were getting kids from Stanford in their dorms trying us out. And lending is really hard. Like you have to know what you were doing and that was not our customer,” Matt explains.

Second, the pricing model couldn’t handle lending’s complexity. “Additionally to that charging per API call, similar to how Twilio does, is very confusing to most people when you’re dealing with lending because the amount of contacts that you get matters based on the lending product you have,” Matt notes.

The lesson: self-service works when individual contributors can evaluate and implement your product. When buying decisions require multiple stakeholders across compliance, engineering, and finance, trying to force PLG wastes time chasing the wrong buyers.

Lesson 2: Cutting Pipeline Can Unlock Growth

“The most important decision that we made, which was a scary one, was this year we cut out a significant portion of our consumer lending funnel. It represented over 50% of our sales pipeline,” Matt reveals. These weren’t theoretical opportunities—they were real companies ready to buy.

Why cut revenue? “We were just spread way too thin, and we needed to go a lot deeper in the market that were being pulled into,” Matt explains. Serving both B2C and B2B lenders meant different regulatory requirements, different product needs, and completely different go-to-market strategies for each segment.

The market was sending signals. “We had massive market pool into the B2B side,” Matt says. The result of focusing? “It has paid off tremendously with massive growth for Canopy in 2024.”

Lesson 3: Match Your GTM to Your Sales Cycle Reality

Enterprise founders often underestimate how long deals actually take. Canopy discovered two distinct buyer segments with radically different timelines. “There are companies who have a system of record, hair on fire, problem, reconciliation,” Matt describes. These brownfield deals move fast.

But they’re the exception. “The majority of companies, it’s a year long journey and we need to have high trust and build relationships with them across many months,” Matt reveals. Year-long cycles demand a fundamentally different approach than transactional sales.

The solution Canopy found: “The combination of content marketing and direct sales, which is all about building trust, is where we are right now. And that is what is most high converting and working for us,” Matt says. Content isn’t for lead gen—it’s sales enablement that maintains momentum during enterprise buying cycles.

Lesson 4: The Go-To-Market Strategy Must Match the Market

Early-stage founders often ask: should we do PLG or enterprise sales? Matt’s answer challenges the question itself. “I don’t think that product led growth is right for every company, every product,” he notes. The real work is understanding your market’s buying behavior.

“You have to think about your distribution and your market and customer in mind. So you can’t disconnect what you’re building from who you’re selling it to and how you sell it and how you go to market will change based on the industry you’re in and the customers that you sell to,” Matt explains.

For fintech specifically, structural factors limit PLG viability: “There isn’t necessarily the virality or referral engine that happens from traditional SaaS PLG when you’re talking about fintech.” The industry, product complexity, and buyer sophistication all determine which go-to-market motion will work.

Lesson 5: Narrow Your ICP to Deepen Your Value Prop

When Canopy tried serving all lenders—”whether you were a B2C buy now, pay later company or you were a B2B revolving charge card company like Brex or Ram”—they discovered a critical problem. “What we realized over time is that actually spread us really thin from a resource standpoint, it was not focused enough from a product standpoint and from a go to market standpoint,” Matt explains.

Different verticals demanded unique compliance approaches, different messaging, and separate sales strategies. Trying to be everything to everyone diluted the entire company—not just the product roadmap, but the entire go-to-market motion.

The fix required courage: say no to real revenue to go deeper in a narrower market. The payoff comes from developing sophisticated buyer understanding that only focus enables.

Lesson 6: Build Multi-Touch Systems for Complex Sales

With year-long sales cycles, the question becomes: how do you maintain relationships without being pushy? Canopy’s answer combines two elements many founders treat as separate strategies.

“That comes in the form of not being, you know, overselling, but really listening and understanding the company, their business model, their future. And it also comes from creating a lot of content to help them understand when is the right time to use us,” Matt explains.

The insight: content marketing and direct sales aren’t competing approaches. They’re complementary motions that work together. Content keeps conversations alive during natural lulls in buying cycles. Direct sales builds the trust and relationship depth that complex enterprise deals require.

Lesson 7: Know When the Universe Is Telling You Something

Perhaps the most valuable lesson isn’t tactical—it’s philosophical. “I always say there’s a fine line for founders of being stubborn is one side and resilient is on the other. And so you get rejected a lot as a Founder, but you also have to know when the universe is telling you something,” Matt explains.

Before Canopy became a B2B infrastructure company, Matt was building a student credit card. He got rejected by every VC on Sand Hill Road, then by Y Combinator at 3am. “I screamed into a pillow that night,” Matt recalls.

A friend gave harsh advice: “You’re an amazing Founder, but this hill that you’re trying to climb is just it’s too much like you really need to take a look and understand what the market is telling you.”

Instead of doubling down, Matt went looking for market pull. He asked large debit card companies if they needed lending infrastructure. “Every single one said yes,” Matt remembers. That signal—not rejection, but demand—led to the pivot that became Canopy.

The framework: “Obviously fail a lot, fail fast, figure it out, run experiments and do what you feel is working and then double down on that,” Matt advises. But the harder skill is knowing when failure means you’re solving the wrong problem, not just executing poorly.

The Adaptation Superpower

Five years in, Matt distills the meta-lesson: “I think that is one of the biggest superpowers of successful companies and founders is being able to adapt and evolve and not being stuck to any one way. And that is true in every functional area of the company, whether it’s marketing, go to market, whether it’s product, whether it’s technology.”

But adaptation isn’t randomness or lack of conviction. It’s pattern matching between what you’re uniquely positioned to build and what the market desperately needs. “You need to be able to change with the customers and be able to continue to offer something extraordinary over time,” Matt says.

The hardest go-to-market decisions aren’t about what new channels to test or what campaigns to launch. They’re about having the courage to cut what’s working but not working well enough—and the wisdom to know the difference.