SaaS & B2B Sales
Running a Software Trial or Pilot
Most trials don't fail. They quietly expire. Nobody agreed what success looked like at the start, so nothing at the end can be called a success, and the deal drifts into the next quarter with everyone still being polite about it.
By Shane McGrath · Published 24 August 2026
A trial feels like progress. Access granted, users onboarded, activity happening. It's the most comfortable form of a stalled deal there is, because it looks exactly like a live one.
A trial without a success measure is a free sample
Not a stage in the deal. If nobody can say what has to be true in six weeks for this to be a yes, then at the end of six weeks nobody will be able to say whether it was. Usage statistics fill that vacuum, and usage is not a decision.
Why sellers agree to them anyway
Because saying "what would this need to show for you to buy it?" feels pushy, and handing over access feels generous. One of those questions saves a quarter. The other spends it.
What to agree before anyone gets access
- The specific thing that should be measurably different at the end, in the buyer's words.
- Who is deciding, and whether they'll see the trial themselves or hear about it second hand.
- Which users are involved, and what they've been asked to stop doing to make room for it.
- The end date, and what happens on it: a decision meeting, in the diary, now.
The mid-point check nobody runs
Halfway through, ask what they've seen so far and what would have to change in the remaining time. Half of trials are already dead at the midpoint and everyone finds out three weeks later. The other half surface a fixable problem while there's still time to fix it.
Be willing to say no to a trial
If a buyer won't define what success looks like, they're not evaluating, they're deferring. Naming that gently is a better use of the next six weeks than running a pilot that was never going to conclude anything, and it usually surfaces the real hesitation, which is a mid-deal objection nobody has said out loud yet.
FAQs
Common questions
- How long should a software trial run?
- Long enough to test the thing that was agreed, and no longer. Extra weeks don't produce more confidence, they produce more time for priorities to change. If you can't say what the extra fortnight proves, don't add it.
- Should we charge for a pilot?
- A paid pilot buys you attention and a sponsor with something at stake, which is usually worth more than the fee. It also filters out evaluations nobody internally is really behind. Free isn't wrong, but be clear about what you're giving up.
- What do we do when a trial is extended repeatedly?
- Stop treating it as a trial and go back to the decision. Repeated extensions almost always mean either the success measure was never agreed, or the person who has to approve it was never really involved.
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