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How Rainforest Engineered Contract Terms Into a GTM Weapon

When Joshua Silver tells prospects that Rainforest‘s standard contract is “overly favorable to the client,” they don’t believe him. Then legal reviews it and sales cycles that typically take weeks close in days.

In a recent episode of BUILDERS, Joshua Silver, founder and CEO of Rainforest, explained how deliberate GTM decisions—from contract design to measuring podcast ROI by qualified lead conversion—have shaped their embedded payments infrastructure company. His nearly 20 years in payments, starting with PatientCo (which scaled to process billions for major healthcare organizations), taught him that in complex B2B infrastructure, the conventional playbook often works against you.

Why Embedded Payments Exists

For decades, software and payments operated separately. Software companies sold platforms, then directed customers to banks or resellers for payment processing. “The two never shall meet,” Joshua explains.

The shift happened when software companies recognized this was inefficient. Why force customers to manage two vendor relationships? The problem: payments infrastructure is hard to build. You need PCI compliance, SOC2 certification, security infrastructure, direct integrations to card networks—all before processing your first transaction.

Toast illustrates the model. Restaurants use Toast for inventory, point of sale, and billing. Toast now processes those payments directly. The restaurant gets one integrated system instead of separate software and banking relationships.

Rainforest enables this for thousands of vertical software companies that want embedded payments but lack the capability to build it. Joshua notes that best-in-class companies generate 50% of their revenue from payments—effectively doubling their business by adding this revenue stream.

Contract Design as Competitive Moat

Most payments companies treat contracts as negotiable documents filled with hidden fees, exclusivity clauses, and punitive terms. Joshua engineered the opposite.

“I actually want our contract to be part of our product,” he says. “I want to invest a lot of time in creating a contract that is in a lot of ways overly favorable to the client so that we don’t have to negotiate it.”

The decision eliminates friction at the most sensitive phase of the relationship. No prolonged legal back-and-forth. No goodwill burned before onboarding begins. Prospects tell Rainforest they braced for adversarial negotiations that never materialized.

Joshua’s calculus: “We’re able to look all of our prospects in the face and say, look, we’ve already given you a phenomenal deal out of the gate. You don’t have to spend a lot of legal time going back and forth.”

His philosophy extends beyond contracts: “Pick the fights that really matter and everything else is just rounding. I think a lot of other founders want to win every last debate. They want to mitigate every risk that their lawyer might highlight.”

This ruthless simplification is a core company value. Joshua asks his team repeatedly when reviewing any deliverable: “Can we simplify it? Can we simplify it? Can we simplify it?” The accumulated effect: dramatically cleaner outputs across product, documentation, and strategy.

Zero Bugs as Cost Reduction

Quality in payments isn’t negotiable. Joshua’s unofficial core value shared with every new hire: “Don’t f with the money.” Nobody wants their paycheck 99% right or 99% on time. The bar is 100%.

Rainforest enforces a zero bugs policy. Not zero bugs created—zero tolerance for living with known issues. “It’s not that we never make a mistake. Of course we have bugs just like everybody else,” Joshua clarifies. “But what we don’t do is tolerate living with them. We don’t have a backlog of bugs to fix.”

When a bug is validated, they fix it immediately. Their head of engineering recently discussed this on a podcast because the policy strikes people as radical.

The ROI isn’t just customer satisfaction. “When you have a higher quality product, you don’t have to invest as much in service because the product just works and you have naturally happy customers,” Joshua explains.

This quality standard differentiates Rainforest in an industry where subpar products are tolerated. Prospects share extensive lists of issues with current processors. Joshua’s response: “Look, we just don’t have those problems. Our system is built to a very high standard.”

Hiring and Training for Technical Credibility

In complex infrastructure sales, prospects arrive with detailed technical questions. Surface-level knowledge destroys trust instantly.

Rainforest maintains one of the highest concentrations of payments talent by percentage—nearly everyone worked in payments or payments-adjacent roles before joining. “Whether you’re talking to an engineer, a support representative or an account exec, they all know how our product really works,” Joshua notes.

But hiring is insufficient. “Never underestimate how much onboarding and training you need to do,” he emphasizes. “The moment that you give bad answers or don’t know your stuff, they’re going to detect that and that’s going to detract a lot from the trust that you’re trying to project.”

Rainforest invests heavily in ensuring every function understands not just how the product works, but why it works that way. The result: technical credibility at every customer touchpoint.

They extend this to customer success by training CS reps on negotiation tactics, value selling, and objection handling—capabilities most post-sale teams lack. “That’s a skill that most customer success teams don’t have and aren’t being invested in to do,” Joshua observes.

The key enabler: strong product-market fit means “we don’t have to sell it that much. It’s really a conversation about solutioning. It’s how can we help our client achieve whatever result it is that they’re looking for and how can our system be configured to do that?”

Qualifying Content by Lead Quality

When asked about podcast ROI, Joshua rejects vanity metrics: “I’d rather have 100 highly qualified listeners that are great targets for us than have 100,000 listeners and not have 100 qualified ones.”

They measure this directly. Every inbound lead gets asked: “How did you find out about us?” An increasing percentage cite The Payment Strategy Show.

The qualitative signal matters more than download counts. Prospects explicitly say: “We were looking for advice on this payments issue, and we heard the podcast and nobody else is putting this content out there. We really appreciate you making that investment.”

Over time, this creates a repository of content that establishes thought leadership. “At the end of the day, the thing that matters is our leads telling you that they’re coming to you because of the podcast,” Joshua explains.

Rainforest applies identical thinking to their Vertex conference for vertical software founders. It’s not a Rainforest sales conference or user event. Attendance is curated—several hundred participants maximum. They select venues that physically can’t accommodate massive scale as a forcing function against growth-for-growth’s-sake.

And they don’t track lead conversion from the event. “We actually don’t measure coming on the heels of that conference how many leads we got. That’s not one of the key metrics. We actually look at NPS score as one of the key metrics. Did people find value in the conference?”

They’re running it twice this year because attendees report it delivers the highest-quality interactions of any conference they attend. Joshua’s philosophy: “Go create value, legitimate, genuine value for the ecosystem and they will come to us.”

Building in Regulated Markets

Joshua calls himself “a glutton for punishment” for building in highly regulated industries. PatientCo operated at the intersection of healthcare IT and payments—two of the most regulated sectors. Rainforest shed healthcare but retained payments regulation.

The constraint: you can’t follow the typical founder playbook of building an MVP, selling quickly, gathering feedback, and iterating. “When you’re building a payments company, you actually have to build so much of the foundation first just to process your very first payment,” Joshua explains. “You have to be PCI compliant and SoC2 compliant. And you have to make sure the security is in place.”

Only after establishing this infrastructure could they begin customer development with close network contacts. Rainforest ran founder-led sales for 2.5-3 years—Joshua personally involved in selling many deals—before building out a scalable GTM function.

His advice for payments founders: “Make sure you know what you’re getting into. It’s a big build and there’s very low tolerance for misses.” Success requires patient capital and realistic timelines that acknowledge compliance infrastructure isn’t optional.

Rainforest partnered with Matrix, Infinity Ventures, and Excel—venture firms that provided capital to build correctly from the start. “We don’t have to rebuild it three or four times,” Joshua notes. “We’ve built the foundations right from the beginning and that’s just allowed us to continue to scale. So we take a lot of long term thinking as opposed to just we’ve got to ship this on this date. It’s do it right, not quick.”

The Long Game

Joshua’s vision centers on Rainforest becoming the default embedded payments partner. When vertical software companies want to add payments or switch from underperforming vendors, he wants Rainforest to be the first call.

The goal isn’t just acquisition—it’s lifetime retention and mutual growth. “We’ve literally doubled the size of companies by adding this valuable payments revenue stream,” he says. “And I love the fact that we get to work with founders day in and day out to help them increase the sustainability of their business and growth and lead to bigger outcomes.”

Rainforest’s approach demonstrates how principled GTM decisions compound in complex B2B infrastructure. Making contracts non-negotiable by front-loading client favorability. Enforcing zero tolerance for technical debt. Training every function deeply on product mechanics. Measuring content by qualified lead conversion rather than volume metrics.

In regulated markets where conventional MVP approaches don’t work and building requires extended timelines before processing the first transaction, these aren’t just tactics—they’re the foundation for sustainable differentiation.