The Future of AI and Win-Loss

Ray Grady is the former President & CEO of Conexiom, advisor, investor and executive with more than two decades’ experience in the tech space. He joined host Ryan Sorley to talk about how businesses should leverage win-loss insights and what the future of AI will bring

1️⃣ Unique datasets will be a differentiator 1️⃣

Ray Grady’s never made a habit of taking on Google or Microsoft head-on. Their pockets are too deep, their R&D too powerful.

Now entering the age of AI, Ray isn’t about to change his approach anytime soon.

“I think those with the deepest pockets and the smartest people will win and that’s going to be just an arms race to the bottom from a cost perspective.”

The opportunity for smaller player lies in their unique, specific (even niche) datasets. Ones that can produce a differentiated output as opposed to the endlessly derivative outputs of the big players.

Add an application layer on top of those datasets and you might have an AI winner.

win loss analysis template

2️⃣ AEs and SEs are the last people you should ask for win-loss intel 2️⃣

You should ask Account Executives and Sales Engineers for their input on why a deal was won or lost. But you need to take their responses with a pound of salt.

Often they’ll say the reason we won is because the AE was the best in the history of selling. And the reason we lost was that the customer was stupid

But when you get a third-party firm to come in and conduct win-loss interviews — removing the emotion and personal interest — you’ll get actionable data to help you win more deals.

And if you’re like Ray, you’ll turn that data into insights and apply it “across every function of my business”.

Watch Ryan’s chat with Chris Fountain, Operating Partner at Frontier Growth

3️⃣ Let the data simmer — don’t overreact 3️⃣

Win-loss data gives you highly reliable, directionally accurate information. But that doesn’t mean you need to immediately react to the findings.

“You don’t want to overreact to one or two win-loss reports. But you can see consistent themes and trends coming out.”

Ray’s advice to execs is to sit still and digest the win-loss data. Take away the personal interest and emotion and absorb the common trends from the data.

From there, home in on a specific customer segment and apply the learnings.

win loss analysis template
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