From Brownfield to Greenfield: How Canopy Segments Buyers by Urgency

From Brownfield to Greenfield: How Canopy Segments Buyers by Urgency

Your pipeline looks healthy on paper—50 enterprise opportunities, all qualified, all “interested.” Then you realize half will close in 30 days while the other half won’t move for a year. Treating them the same kills conversion on both sides. In a recent episode of Category Visionaries, Matt Bivons, CEO of Canopy, shared how discovering two fundamentally different buyer segments hiding in their pipeline transformed their entire go-to-market approach.

The Two Buyer Segments Nobody Talks About

Most B2B founders segment by company size, vertical, or budget. Canopy discovered a more useful segmentation: buyer urgency. Not urgency in the sense of “interested” versus “just browsing”—urgency in the sense of whether they have a problem today or are planning for tomorrow.

“There are people who immediately want to have a pain Point of either launching a lending company, we call them greenfield opportunities and therefore they come to us as new lenders,” Matt explains. These are companies not doing lending today but planning to get into it. They’re building something new.

Then there’s the second segment: “And then there are companies who have a system of record, hair on fire, problem, reconciliation,” Matt notes. These brownfield deals come with existing infrastructure that’s actively failing them. The pain is acute, immediate, and costly.

The distinction isn’t semantic—it determines everything about how you sell, how long deals take, and what messaging resonates.

Why Brownfield Deals Move Fast (But Are Rare)

Companies with hair-on-fire problems don’t need education about why they should switch. They already know. Their current system can’t support new product launches. Their reconciliation process is breaking down. In fintech specifically, the stakes are high—there was “a bunch of stuff in the news around Synapse and fintechs that couldn’t find people’s money. It’s obviously a big problem,” Matt notes.

These brownfield buyers come to Canopy because they’re restricted. “They can’t do something, they can’t innovate, they can’t offer a second product, they are restricted in some way,” Matt explains. The value proposition is immediate and obvious: “We are one of the most fast, flexible systems.”

But here’s the challenge: these urgent buyers are the minority of the market. Building your entire go-to-market motion around brownfield deals means limiting yourself to companies already in crisis. You’re competing on speed and hoping competitors’ products fail fast enough to create demand.

The Greenfield Reality: Year-Long Sales Cycles

Greenfield opportunities—companies launching new lending programs—represent the majority of Canopy’s market. But they require a completely different sales approach. “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.

Why so long? These companies aren’t solving today’s crisis—they’re planning tomorrow’s product launch. They need to:

• Build business cases for new product lines
• Get budget approval across multiple departments
• Navigate compliance and regulatory requirements
• Align stakeholders from product, engineering, finance, and legal
• Evaluate multiple vendors and alternatives
• Plan implementation timelines

None of this happens in a 30-day sales cycle. “It also mattered around how many touches we actually needed to move people through our funnel,” Matt notes. The question becomes: how do you stay engaged during a year-long evaluation without being pushy or burning out your sales team?

Building Different Motions for Different Urgency Levels

The insight that transformed Canopy’s go-to-market: these two segments need fundamentally different approaches. For brownfield deals, speed and technical credibility matter most. For greenfield deals, trust-building and education dominate.

“That comes in the form of not being, you know, overselling, but really listening and understanding the company, their business model, their future,” Matt explains. This isn’t generic relationship-building advice—it’s specific to greenfield buyers who need a partner that understands where they’re going, not just what they need today.

The content strategy differs too. “It also comes from creating a lot of content to help them understand when is the right time to use us,” Matt says. This content isn’t about product features—it’s about helping prospects recognize when their current path will hit limitations and when switching makes strategic sense.

Content Marketing as the Long-Cycle Strategy

For year-long enterprise sales cycles, the traditional outbound playbook breaks down. You can’t maintain weekly check-in calls for 12 months. You can’t keep sending “just following up” emails. You need a way to stay present without being annoying.

Canopy’s answer combines content marketing with strategic direct sales. “I would say 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.

The content serves a specific purpose: keeping Canopy top-of-mind during the natural lulls in enterprise buying cycles. When a greenfield prospect is waiting on budget approval, navigating internal politics, or building their business case, educational content maintains the relationship without requiring sales team time.

The SAM vs. SOM Framework

Matt’s thinking about these buyer segments connects to a broader market segmentation framework. He breaks down Canopy’s market into three layers:

TAM (Total Addressable Market): “Any small business or FI that needs liquidity.”

SAM (Serviceable Addressable Market): “Companies that are already lending today… they can’t build flexible product types. They are limited on what they can offer their customers. They are working with rigid systems.”

SOM (Serviceable Obtainable Market): “Greenfield new lenders. So these are companies that are not doing lending today that want to get into lending.”

The distinction matters for resource allocation. “As we think about the verticals and the product types, the tam, SAM and sam, it’s important for us to develop marketing and messaging and our go to market strategy has to be tailored to each of those companies in those categories. It is not a one size fits all,” Matt explains.

Brownfield deals (SAM) get one motion. Greenfield deals (SOM) get another. Trying to use a single approach for both dilutes effectiveness on both sides.

The Multi-Touch Reality

Understanding buyer urgency also reveals why traditional B2B metrics can mislead. If you measure average sales cycle across all deals, brownfield deals make your team look efficient while greenfield deals look like they’re struggling. But that’s comparing fundamentally different motions.

Matt’s insight: measure and optimize separately. Fast-moving brownfield deals need rapid response, technical depth in sales calls, and proof of reliability. Slow-moving greenfield deals need patient relationship building, educational content, and strategic business case support.

“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. For Canopy, this meant running different experiments for different urgency segments rather than trying to optimize a single funnel.

The Practical Takeaway

Most founders know intellectually that not all buyers move at the same speed. Few act on it by building genuinely different go-to-market motions for different urgency levels.

The framework Canopy discovered:

Brownfield (urgent, existing infrastructure failing):

• Lead with speed and flexibility
• Focus on technical credibility
• Sales-driven motion with fast follow-up
• Case studies showing successful migrations
• Emphasis on reliability and feature completeness

Greenfield (planning, no existing infrastructure):

• Lead with education and partnership
• Focus on business model understanding
• Content-driven motion with patient nurture
• Thought leadership showing market expertise
• Emphasis on vision alignment and future roadmap

The hard part isn’t recognizing these segments exist—it’s having the discipline to treat them differently even when it complicates your sales process, splits your marketing budget, and makes your metrics harder to report.

But for Canopy, that segmentation became the foundation of their go-to-market success. Sometimes the best optimization isn’t making one motion work better—it’s admitting you need two different motions entirely.