Using GenAI to Design a Win-Loss Program

Ryan Sorley is the VP of Win-Loss at Klue, the founder of DoubleCheck Research and the Host of the Blindspots Podcast on the Compete Network. He joined Adam to tell us about Season 3 of Blindspots and give us his three biggest takeaways for anyone starting a win-loss program. Here are those takeaways

1️⃣ Align your win-loss program goals to organizational goals 1️⃣

Step one: get a handle on the broader strategic direction and goals your leadership team has set for the year.

Step two: talk to them and put those goals in the context of a win-loss program. In other words, ask them what kind of intel and insights they would like to see from a win-loss program that would support their goals.

“Find out what they’re looking to learn through the program so they can lean in with you and share the value across the organization.”

ServiceTitan’s Director of Marketing Strategy Jenn Roberts shared why she thinks win-loss intel is essential for understanding her customers, and what it takes to get organizational buy-in last year on the Competitive Enablement Show.

Check out the full interview and three quick takeaways here.

2️⃣ Set your segmentation strategy 2️⃣

More data is not always better — especially when that data is imperfect. Unless you’re sending someone to the moon, getting directionally accurate data is a more realistic and achievable goal than data with 95% certainty.

Ryan recommends segmenting the opportunities you’re looking to understand (by size, by vertical, by location) as opposed to doing everything all at once.

“A lot of companies tend to cast a wide net out to all of the opportunities to collect data. You don’t have to do that.

With 15 to 20 well-crafted win-loss interviews, you can extract a lot of valuable insights to deepen your understanding of a particular segment.

This will narrow your focus and give you a better chance at succeeding.

Buyer and competitive insights from win-loss have been key to Vijay Gupta’s success. Find out more on the Season 3 Premiere of Blindspots with host Ryan Sorley

Interviews yield more insights than surveys

Interview data is the gold standard for win-loss insights. Partly, that’s because of how difficult it is to craft a good survey.

You need to make sure the questions are easily understood, that you’re asking the questions with enough open-endedness to avoid leading your interviewee, but not so much so that you don’t get the intel you want. And you need to make it long enough to be comprehensive, but no so long your interview subjects develop fatigue.

“[With interviews] you’re going to get the story behind the reasons. You’re going to get the insights that really can drive the right types of actions within your your organization.”

Like former CEO of Demandware Tom Ebling said on a recent episode of Blindspots, win-loss interviews surface the nuances of a deal — nuances that are much more difficult to capture with survey or CRM data alone.