By Rob Kall, Co-Founder & CEO, Cien.ai

“Poker is so volatile that it’s possible for a theoretically winning player to have a losing streak that persists for months, or even for a full year.”

– Nate Silver, Statistician & Author

The Cold Streak

Every experienced seller knows the dreaded feeling of a cold streak. Weeks or months go by without a single win.  

Instead of despair, it is sometimes useful to think like a seasoned poker player. You win a hand based on 3 factors: Your cards, your skills and luck. 

Your cards are what they are. Your skills are mostly needed to determine the value of your cards and your game strategy. Is this hand worth playing, or should I fold?  Your luck: That is something you can’t control, so no point sweating that. And the truth is that in the long run all poker players are equally lucky…

The same analogy applies to your pipeline…

The Solution

Professional poker players don’t just look at the cards. They calculate expected value (EV).

Expected Value (EV) = Deal Value × Probability of Winning

Sales teams should do the same. Instead of asking “How big is this deal?” ask:
How likely is this deal to close and at what amount? 

Here’s a simple illustration:

A rep chasing ten “high card” deals is far worse off than one focusing on a few “full house” opportunities. 

What Does Success Look Like?

Sales teams stop measuring pipeline by raw dollars and start managing it by expected value.

At Cien.ai, we do this every day for all our clients using our proprietary tech. 

Our AI-driven propensity models:

• Predict the true probability of winning each deal  as Propensity to Win
• Estimate the realistic final deal value which includes typical discounts and other adjustments 
• Provide a transparent expected value for every opportunity 
• Aggregate this for sales leadership as Adjusted Pipeline 

This allows sellers and revenue leaders to:

• Prioritize high-value, high-probability deals 
• Reduce wasted effort on low-quality pipeline 
• Forecast with significantly higher accuracy 
• Understand why certain deals are more likely to close 

Instead of relying on stage-based assumptions or gut feel, you get a real-time, data-driven view of your pipeline’s true worth.

And just like in poker, over time, consistently playing positive EV hands is what separates winners from everyone else. 

About the Practical RevOps Analysis Series

This article is part of our Practical RevOps Analytics Series, inspired by our work with B2B business leaders, growth consultants, and PE operating partners. These articles focus on the technical aspects of improving GTM performance. For business-focused strategy content, check out our companion series, Growth Essentials Series.