🔆 How to win SaaS deals where your chances are <3%?

TL;DR -Once we approach a deal with humbleness – doors open, not close.

Customers don’t sign for value alone. There are more forces at play. Just think about the different agendas of different stakeholders. It’s especially true in enterprise SaaS sales. 

Let me illustrate this with an example Rutger Teunissen gave me – founder of 24Sessions.

“It was probably 2017 or 2018, and we’ve been piloting with that bank for a long time. All the results were great; all advisors loved us. The next step would be to scale it up, which would have been a million-dollar deal for us. 

I remember being in that sales meeting. It was the best we ever did. Everybody was excited. So, at the end of the session, I asked them (because I knew we had some opponents who preferred to use Skype): ‘Before the meeting, you told me our chances to win was 1%. So what are our chances now? And they said: ‘You’ve done so well; you answered everything. So your chances are now 3%.”

They were not even joking. It was a serious assessment. So I realized, as a small startup, especially when you want to deal with large enterprises, you can do everything right, but still, they might go for Microsoft or SAP.

So this could have been one of these moments where we said: ‘This is never going to work.’ But we saw something positive out of it. It took us six to nine more months, but in the end, they became our (then) largest customer and a lighthouse customer that gave the trust to all other organizations to follow.”

Here’s the thing

Becoming the obvious choice requires more than a great solution and remarkable value. Remember – you’re dealing with people.

When I asked Rutger what made the deal happen, he answered: “Being extremely humble.”

Humbleness is not about giving in to everything a customer asks or says. On the contrary. It’s about:

  • Acknowledging that no matter how successful you are – it’s not about you.
  • Leveling with the other side instead of pretending you’re the smartest in the room.
  • Accepting the other side will always have strong preferences based on valid arguments.


Question for you to reflect upon

How many SaaS deals would you have won in the past year if you’d approached them more humbly?


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About the author

Sales Pitch

Ton Dobbe is a former B2B software product marketer who's on a mission to save mission-driven SaaS CEOs from the stress of 'not enough' traction. He's the author of The Remarkable Effect, the host of the Tech-Entrepreneur on a Mission podcast, and writes a daily newsletter on the secrets to mastering predictable traction.