How to
Running a win loss analysis from what is already in your CRM.
A win loss analysis from CRM data compares the activity on deals you won with the activity on deals you lost, at the same point before each ended. It answers what separated them without a single interview, and it is a good first pass before spending time on interviews.
What to pull.
For every closed deal, export the outcome, the close date, the owner and the activity: emails and replies, meetings, notes, stage changes and the contacts attached.
What to compare.
Pick one point shortly before each deal closed and count everything that had happened by then. For each signal, how often did it show up on the wins, and how often on the losses?
A signal that shows up far more on wins is a predictor. One that shows up evenly on both is noise. One that shows up more on losses is a warning, even if everyone thinks of it as positive.
The traps.
Scoring after the close, which flatters every win. Mixing points in time, which compares late deals with early ones. Reading a pattern on a handful of deals as a finding. And stopping at the average, when the useful part is which signals moved it.
Where interviews fit.
The CRM tells you what separated wins from losses. It cannot tell you why a buyer felt the way they did. Use the analysis to decide which deals deserve an interview and what to ask.
Questions
How do I do a win loss analysis without interviews?
Compare what happened on your won deals with what happened on your lost deals, at the same point before each one ended, using the activity already in your CRM. The signals that appear far more often on wins are what separated them.
What CRM data do I need for a win loss analysis?
Each closed deal outcome and close date, plus the dated activity on it: emails, replies, meetings, notes, stage changes and contacts added. Deal amount and creation date sharpen the comparison but are not required.
How often should I run a win loss analysis?
Quarterly is common, and again after any change to your product, pricing or target customer. A signal that predicted wins last year can stop doing so, which is easy to miss unless the test is repeated.
It arrives in Slack
Every morning, each rep gets one message naming the deals on their own book that moved overnight, biggest mover first, with the reason beside each number and the deals that have gone quiet underneath.
$99 a month, cancel any time.. Everyone on the team. No per seat charge. Connect a CRM and it runs. No implementation fee. 14 day trial. No card.
Related reading
Back testing a deal score against your own closed deals
A back test scores deals you have already closed as they stood before they ended, then checks the scores against what happened. The steps.
Which of the signals in your CRM predict nothing
Most teams trust signals they have never tested. Reply speed, email opens and meeting count can all carry no information. How to find out which.
How to tell which of your open deals are actually real
Every pipeline has deals that are alive and deals being carried. The difference shows in what the buyer did, not the stage somebody dragged the card to.
A free back test of your deal score, on your own closed deals
Kaypo Hindsight is a free, read only back test. It reads your closed deals and reports what separated the ones you won from the ones you lost.
Reviewed September 20, 2026 against the product as it behaves today.