The "Yes, If" Move That Turns Enterprise Pilots Into Company-Wide Deals

The Insight

A big enterprise dangles a pilot. Ten people, low risk, "let's see how it goes." Most founders grab it, because a logo is a logo. Christian Lund, co-founder of Templafy, found the option between yes and no.

When one of the Big Four accounting firms wanted to start with a ten-person trial, he didn't refuse it and he didn't just accept it. He said "yes, if."

The "if" was two conditions: agree exactly what we're proving, and agree what happens once we prove it. That turned a throwaway trial into a company-wide rollout. And when some of those deals later opened up to competing vendors, Templafy had usually already written the criteria everyone else got scored against.

The rule: never run a pilot to find out whether they like you. Only run one to prove a specific thing you both defined in advance.

How They Did It

1. Reject the "do you like it" POC. Christian's words: "We would never go into a POC to see do you like it. We would go into that to see does it work." A pilot with no pass or fail line proves nothing.

2. Pin down the proof criteria before anything starts. His example was mundane on purpose: when you open the document, does the add-in appear? When it populates, is the output correct? "We have to agree on what we're proving. Otherwise we're just wasting everyone's time."

3. Agree what comes after. If the criteria are met, what's the deal size, the rollout, the timeline? He nailed that down up front, not after.

4. Walk if the basics aren't there. No real budget, no timeline, no genuine intent to buy? They passed. Hard, but he'd been burned enough to hold the line.

What Trips Up Founders

Trading the strategy for the logo. The Big Four name in front of you feels like the win. Christian saw that a stack of unqualified pilots would sink him: "we're just gonna run like a thousand POCs, not gonna get anywhere." The logo is bait, not the deal.

Leaving "what's next" for later. If you prove the thing but never agreed what a win unlocks, you've handed the buyer a free trial and kept all the risk. The conversation about rollout and price is easiest before the work, not after.

Confusing motion with progress. A pilot in flight feels like a deal moving. Without defined proof points, it's just your team's time leaking into someone else's evaluation.

When This Doesn't Work

If you're pre-product-market-fit and genuinely don't yet know what "it works" looks like, you may need exploratory pilots to learn. Fine. But even then, name the one thing you're trying to learn and what you'll do with the answer. The failure isn't running a pilot. It's running one with no definition of done.

The Question

Before you agree to any trial, ask: "If this succeeds, what exactly will we have proven, and what happens the moment we prove it?"

If you can't answer both halves, you're not ready to start. Sort that out first, and a small pilot stops being a trap and starts being the on-ramp to the whole account.