Customer Marketing
How to Run a Win/Loss Program with 8 Customers
Win/loss is supposed to require dedicated headcount and a research firm. It does not. Here is the lightweight version.
Most B2B companies skip win/loss analysis until they are large enough to hire a dedicated researcher or pay Klue or Crayon. The skip is a mistake. Even at 8 closed-won deals, a lightweight win/loss program produces decision-altering insight.
The lightweight version: every closed deal (won or lost) gets a 30-minute call with the buyer within 30 days. The call is run by the CMO, a senior PMM, or a fractional researcher (cheap on Upwork). The script is six questions: how did you discover us, how did you evaluate us, who else did you evaluate, what tipped you toward (or away from) us, what would you have done differently, what are we doing wrong that we should fix.
Document the calls in a shared doc. Read the doc as a leadership team monthly. Two patterns will emerge in the first quarter. The patterns will surprise you. Act on them. Then keep doing it.
The reason win/loss is undervalued is that the insights feel anecdotal. They are not. After 20 calls, the patterns are statistically meaningful. After 50, they are decision-altering. Most companies never do the work because it feels small. The companies that do it consistently make better product, marketing, and sales decisions than competitors who do not.