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Doing the work

They want a pilot before they commit. How do I run one that ends in a contract instead of a shrug?

Most pilots fail because nobody wrote down what winning looks like, so at the end everyone says nice things and nothing happens. Fix that at the start. Charge for it, even a small amount, because a free pilot is a free trial wearing a suit and it will never reach the top of anyone's list. Put it on the paper you actually want signed: a one year agreement with a termination right at the pilot date, so converting is a non event rather than a fresh negotiation. Pick one metric that matters to the economic buyer, agree it in writing, and agree the kill criteria too (setup not done by day seven, buyer misses the midpoint review, nobody touches the core workflow). Keep it to 30 days. Ninety days is not urgency, it is a place deals go to die.

Go deeper

4 resources, 4 link-checked.

📄 Article
✓ Link checked Free Intermediate

The source of the two moves that turn a pilot into a contract: put it on a full year agreement with a termination right, and keep it to 30 days so it stays at the top of someone's list.

How to Execute SaaS POCs that Convert

From Heavybit by Ashley Dotterweich 10 min read

  • Charge at least a token fee, it is the cheapest qualifier you have.
  • Run 30 day pilots, not 90, because a one month clock keeps you at the top of their list.
  • Pick exactly one KPI with business impact, not a list of success criteria.
  • Paper the pilot as a full year contract with the right to terminate, so you do not renegotiate legal terms at the finish line.
Open heavybit.com
📄 Article
✓ Link checked Free Intermediate

Gives you the benchmark to judge your own pilots against (roughly 60 to over 90 percent) and explains what drags the number down, which is usually heavy process change at the customer or reps closing pilots they should have walked away from.

What is the typical conversion from paid pilot to annual contract in B2B SaaS?

From SaaStr by Jason Lemkin 5 min read

  • Paid pilot to annual conversion runs roughly 60 percent to over 90 percent across the companies Lemkin works with.
  • EchoSign cleared 90 percent because pilots always ended fully in production, not just switched on.
  • The 60 percent case was a product needing heavy business process change, which improved as customer success got stronger.
  • Bigger brands switch from opt in pilots to opt outs with a 60 day cancellation window, and often see less churn.
Open saastr.com
📄 Article
✓ Link checked Free Intermediate

A usable template for the document you should agree before the pilot starts: business outcome, usage milestone, stakeholder review, timeline, and the failure criteria that let you call it early instead of drifting.

Pilot Customer Success Criteria for B2B Startups

From Do What Matter 11 min read

  • Pilot criteria need five parts: business outcome, usage milestone, stakeholder review, timeline, failure criteria.
  • If it does not fit on one page, the pilot is too broad.
  • Write the decision as one sentence: by [date] we will decide whether [customer] will [commercial action] based on [criteria].
  • Score the final review green, yellow or red per category rather than inventing numeric precision.
Open dowhatmatter.com

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