Pilot Contract

For a long time, bringing a new tool into a company was a single large decision. A buyer would sign a three-year agreement covering 300 people, and everything available before signing was a sales pitch and an hour-long demo. Whether the product actually fit the way that team worked, whether existing files could be moved over, whether the security reviewer would object — all of it surfaced only after the signature was on the page.

So the people evaluating the purchase kept postponing. With no way to check, waiting was the safer choice. The team lead would say they wanted to try it but couldn't promise three years, and the seller would answer that they should sign now and adjust later if it didn't fit. Neither side could accept the other's word as collateral, and deals sat still for six months at a time.

A pilot contract splits that one large decision into two smaller ones. First comes a small agreement covering one team of twenty-five people for three months. The result of those three months decides the company-wide rollout. The buyer's downside shrinks from three years of spend to three months of it, and the seller's time to signature drops from half a year to about three weeks. Nothing clever happens here beyond replacing a verbal assurance with real usage.

Six things go into the document. Most of them also appear in a full contract, but the last two exist only in pilots.

1. Term — the start and end dates, written as dates rather than a duration. One to three months is typical. One month ends before anyone gets comfortable with the product; past six months, the decision simply keeps sliding.
2. Scope — which team, how many people, and which features. Something like twenty-five people in marketing, the full paid feature set, external sharing excluded.
3. Price — free or paid, and if paid, how much. Roughly half of list price is common.
4. Support commitments — who helps with what during the window. A named contact, help migrating existing files, and a response-time promise belong here.
5. Success criteria — the numbers that define a good outcome, agreed in advance. For example: twenty of the twenty-five people log in at least three times a week, and 100 team documents have been migrated.
6. What happens at the end — the terms and price of the full contract the pilot converts into if the criteria are met, the wind-down procedure if they aren't, and what happens to the data either way.

Leave out the last two and the document has a deadline but no standard to judge against. Three months later the answer is "let's use it a bit longer before deciding," and the same terms get extended two or three times over.

The seller drafts it. A sales rep fills in the term, scope and price, then checks those figures against the quote already sent. Success criteria are the exception: the rep does not set them alone but writes them with the customer's team lead. Criteria written by the seller tend to line up with whatever the product does well, and hitting a number the buyer never cared about does not move a rollout forward.

Three people read it. The first is that team lead, who looks at the term, the scope and the criteria and judges whether their team can actually get there in three months. The second is the customer's legal and security reviewer, whose attention goes almost entirely to where data is stored and how it gets deleted afterward. A small price tag rarely buys a lighter review — many companies run pilots through the same process as a full purchase. The third reader sits on the seller's side: an internal approver checking whether the discounted figure trips the discount policy, and whether the discount could be read as carrying over into the full contract.

The document is short; the review around it is less so. A non-disclosure agreement (NDA) usually has to be in place first before either side can share files, and a customer large enough to insist on a master service agreement (MSA) may push that negotiation into the pilot stage as well.

"Three years looks like a hard ask, so let me propose a three-month pilot with the marketing team first."

The big contract is stuck, so the seller is shrinking the size of the decision to get the door open.

"We need to agree on the pilot success criteria this week."

Without that agreement there will be nothing to judge against when the window closes.

"That account has extended its pilot twice. I'm taking it out of this quarter's forecast."

A pilot that keeps stretching reads as a rollout that isn't going to happen.

At Pagedeck, accounts above roughly 200 employees almost always get a pilot proposed first. When Sofia raises a three-year contract and the buyer hesitates, she reframes it on the spot as one team for three months, then writes the success criteria with the team lead on the next call. Once the window starts, she checks the login count and the number of migrated documents every two weeks, and if either sits below half the target she works out with Grace what else the team can offer in the time left.

The meeting on the final day is short. They read the numbers written into the contract, and if the numbers are there, the full contract goes out on the terms agreed months earlier. If they aren't, the deal closes with a recorded reason. The only version of that meeting that runs long is the one where nobody wrote criteria down.

The most common mistake is treating a pilot as a free trial. Both are short, limited looks at a product, so the confusion is understandable. But a free trial starts with a button and ends with nothing owed in either direction, while a pilot is a signed agreement that creates obligations on both sides. The seller owes the support written into it; the buyer owes an evaluation against the criteria written into it. Miss that difference and a seller spends three months of a named contact's time and gets no answer at the end of it.

The other mistake is reading a signed pilot as a deal that is effectively closed. The customer signed something, so the rest looks procedural. A pilot exists to check an assumption, though, which means the check can fail — and even a delighted team lead is no guarantee, because the customer's budget owner can still balk at a contract term locked at three years. Counting pilots as won revenue makes quarterly results miss the target every time, and after a few quarters of that nobody trusts the forecast at all.