The PWIN Paradox of Enterprise Sales

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“There can be only one…”. − The Highlander

One of the tools put forth in my article on how to execute enterprise sales is the Probability of Win (PWIN) calculation. There is a paradox here, though. Let me explain:

You are eventually going to mature your playbook and drive your PWINs to 100%. Trust me, I’ve done this enough times, it is going to happen, everybody does it. Humans, and sales people in particular, are not good at being objective. Everybody’s gut tells them they are going to win and we will interpret data to prove it. However, even if you truly have an objective process, you are eventually going to start submitting bids that check all of the boxes and looks like a 100% proposal.

Congratulations, you went from college ball to the major leagues. It is an entirely different playing field, and now you are competing with an entirely different level of competitor.

This is where the paradox starts — your competitors are going to develop a 100% PWIN strategy too! How do I know? Because they are just as hungry and focused as you are to win. Your potential customer is going to get a set of 100% PWIN proposals — they each should truly be spectacular in their own way — yet the customer will only pick one.

And now the paradox appears — if there are N proposals — and only one wins, then your winning chance was never higher than 1/N to begin with. It can’t be 100% unless this is a sole source competition or unless your competition, quite simply, isn’t (competitive).

I have never found a way around this problem. It is critical that you create a deliberate sales playbook and process, and I have found the PWIN approach to work well for my management style and approach to sales. Once you have established that playbook, you are now competing at a peak performance level in what is likely a very competitive market. (Unless you are the first one there, in which case, rule the world!). But at most, your chance of winning should be theoretically capped at 1/N.

Look, if you didn’t do your homework in the first place, you have no chance, so you have to push that PWIN. But in the end, like in any competition, there are going to be other elite competitors present, and only one of you will win.

The Takeaway

Until you flesh our your sales playbook, you are not competing at an elite level. Once you have figured out how to submit 100% PWIN proposals, you will move into an entirely different level where everybody is submitting very responsive bids. If you have N comparable competitors (don’t forget internal R&D is competition), then your pipeline needs hold a multiple of N times your target revenue to achieve on target earnings (OTE).

This article originally appeared in TheEntrepreneurd. I use my background as a co-founder who has dabbled in business development, software development, sales, and angel investing, to create original and synthesized thought content related to the world of entrepreneurship and startups. 

The thoughts and musings presented in this article are my own, with the exception of those that aren’t, and I always give credit where credit is due.  I would love to hear your thoughts, feedback, and insights. Get in touch at:

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