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Bruce Kasrel, VP Research
Bruce Kasrel, VP Research Posted on October 26, 2021

How Win/Loss Data Can Help You Kick Ass at Sales Kickoff | Podcast

The ultimate goal of any sales kickoff (SKO) is to give the sales team the tools, insights, and strategies they need to a) understand what’s working and what’s not, and b) get back out there and close more business!


In a recent Fireside Chat, I had the chance to explore the most effective ways to use win/loss data to help achieve those goals. I was joined by Miko Bird who runs global competitive intelligence as the Head of CI at Optimizely, and Chris Herrin who—as the Senior Product Manager at BeyondTrust—gives his sales folks straight talk about their strengths and weaknesses.

“Sellers want to hear about wins, and the SKO is a great opportunity to do breakout sessions about both wins and losses,” Miko says. “The SKO also gives us a chance to share best practices and expertise with a lot of different teams across the entire organization beyond sales.”

Chris emphasizes the importance of giving sales real information that they can use, “They want to hear about wins, and—more specifically—how to blow their quota out of the water. They love honesty, and they appreciate when we show our cards in terms of the research we’ve done.”

We had a lively conversation that covered a lot of great ideas for how to make the most of win/loss information to engage, educate, and even inspire your sales team at a SKO.

Planning Ahead

The first piece of advice our experts shared was to avoid waiting until the last minute. “No one has time to read fifty win/loss interviews as you’re preparing for your SKO,” Miko says. “It’s much better to spread your prep out over the course of the year. 

Both Miko and Chris leverage their DoubleCheck workspace powered by Dovetail to identify and compile quotes and other relevant information. The goal is to build up a curated collection of bite-sized bits of data that you can access quickly and easily when the time comes. 

Chris puts particular emphasis on finding strong customer quotes. “Customer quotes are the most effective way to drive the message home with sales,” he says. “They might hear the same message from an internal source—like a product manager or the marketing team—but when it comes directly from a customer—unpolished and direct—it means a lot more to the sales team.”

Another reason to continuously work on SKO win/loss preparations is that you’ll have the ability to make highly informative comparisons between the beginning of the year and the end of the year. “Look for instances when a release, change in strategy, or change in messaging made a measurable improvement in sales outcomes,” Chris explains. “This shows the sales team that you’re not only listening to the market, you’re doing the strategic work to make a real difference. You’re not just throwing darts at a dartboard. Giving sales a behind-the-scenes look at the work helps raise excitement about future releases while building confidence in the competitive [win/loss] research.”

Finding the Perfect Win/Loss Quotes

We’ve already established the importance of getting win/loss intel “from the horse’s mouth,” so to speak. But how do you recognize a valuable SKO win/loss quote and present it to the best effect?

Miko keeps an eye out for quotes that clearly spell out why someone chose her company over the competition, especially if the reason ties back to a tool that salespeople may or may not be using to its full advantage. “When a customer shares that their decision was based in part on the fact that they attended an event, conference, or webinar, that’s really powerful,” she says. “That kind of quote highlights how creating better customer engagement can actually help close deals.”

Chris focuses on quotes that mention chief competitors or insurgents. It doesn’t matter to him if the quotes put his company in a positive or negative light, only that the quote provides real-world context that helps salespeople really get inside a prospect’s head. “Salespeople want to know what the sales cycle feels like to the other person,” he says. “They want to know which part of the sales process matters most—what is the ‘hinge’ moment where they can make a big difference. That’s the kind of information that will change a sales team’s behavior.”

Adapting Your Executive Summary Deck for the SKO

In any kind of presentation, it’s critical to tailor your content to your audience. Otherwise, you risk people tuning out or even walking away with the wrong takeaways. Chris worked with his DoubleCheck Research Director to refine the standard stakeholder win/loss deck so they could co-present on the main stage at the SKO. To ensure that the deck would hold the sales team’s attention and deliver information they could actually use, they:

  • Opened with information on a good note by highlighting how well sales was connecting with customers.
  • Removed any mentions in which the influential factor was something sales could not control directly. These factors included things like product features, persona research on buyer profiles, and ineffective marketing materials.
  • Prioritized quote slides over data slides. While they did share data on how they compare to other companies (for benchmarking purposes), they weighted the presentation to include more direct customer input.
  • Got really specific about exactly how the competition is selling so the sales team could get a really clear picture of the difference in selling styles and how those differences affect outcomes. 
  • Turned up the volume on areas that sales might otherwise overlook. For instance, they highlighted the importance of having salespeople step in to assist with the red tape of last-mile negotiations like signing legal documents. 

Delivering Negative Feedback

No one likes to hear bad news, but knowing what’s not working is often just as valuable as knowing what is working. The trick is in knowing how to deliver the “loss” part of the win/loss feedback in a way that is effective and productive instead of shaming or otherwise demoralizing. 

Miko finds breakout sessions with different groups to be a great starting point. Sometimes these sessions target specific functions (such as sales engineering or solution architects), and sometimes they target a specific region and the relevant competitors. 

From there, Miko creates an open forum so that sales executives can learn from each other. “SEs don’t always have the benefit of direct feedback because they aren’t always invited to the debrief with the seller and the customer. They’ve already moved on to the next opportunity,” she explains. “The open forum usually creates a very lively session in which sales engineers can learn from each other by sharing what they’re encountering in the market and how they’re overcoming a variety of challenges.” 

Chris, who comes from a sales background, actually likes talking about losses. “I’ll tell sales exactly why we lose,” he says. “It’s important to be able to just flat out tell sales the reasons. They want to know.” 

Of course, Chris makes sure to balance that information with insight into how they are transforming those losses into wins. He does this by looking at losses that happened at the beginning of the research effort and then walking sales through the changes that were made to change the outcome. Highlighting the before-and-after difference in performance gives sales valuable information as well as encouragement. 

Finally, Chris believes in acknowledging that sales is a numbers game, and not every opportunity is going to be perfect for your organization. “There are some problems you’re not best suited to solve, some things that aren’t really in your scope,” he says. “It’s better to learn to identify these early in the sales cycle so you don’t spend time pursuing something that’s never going to work out. You have limited resources, and you need to spend those resources on the right opportunities.”

Sharing Win/Loss Information with Non-sales Teams

Win/loss intel is valuable to every part of an organization, not just sales. But whether or not a team receives that value often depends on how the intel is presented. You need to make sure you’re highlighting the findings that are relevant to each group and speaking their language in the way you talk about them.

Sales is most interested in learning which parts of the sales cycle are most vital to a prospect. For example, what is a prospect looking at before talking with a sales rep—analyst reports, the website, self-education articles? That information may be much less important to the product team, so—again—you need to cherry pick the most salient bits of information based on who you’re talking to.

For instance, when Chris talks with the product team, he knows they will be most interested in feedback about the current offering, product roadmap, and overall product direction. He knows information about pricing and packaging will resonate well with this group, as will any data or quotes that measure prospect confidence in the company’s ability to execute on promises and outpace competitors. “I provide feedback completely unfiltered,” he says. “If it’s your product, I want you to read every single word in there so you understand all the stones you need to overturn to make the right decisions going forward.”

Miko finds that win/loss data is a perfect complement to competitive intelligence. “The competitive insights we gain from customer interviews feed back into battle cards and other competitive assets,” she says. “But we get so much more than just product-related feedback. We’re also hearing about marketing-specific elements like messaging, positioning, and pricing.” She also points out that the SKO is typically where you’re announcing updated selling assets and tools, and it can be helpful to be able to share how win/loss data has shaped those new resources.

Maximizing Impact for Your Next SKO

Using win/loss data effectively at your next SKO requires a little up-front planning, intentional presentation, and remembering why you’re sharing this information in the first place. 

Miko recommends reviewing key win/loss interviews well ahead of time because they can help you generate ideas about how to focus your SKO presentation. “Pay special attention to interviews that feature rip-and-replace situations in which you unseated top competitors,” she says. “And take advantage of opportunities to identify patterns. We review all the data we’re getting back from DoubleCheck to isolate recurring themes quickly and easily.” 

From there, Miko focuses on making the information as engaging as possible while creating a learning experience that doesn’t put people on the spot. 

Chris’ first piece of advice is “get out of your own shoes.” In other words, think about the day-to-day life of the person you’re presenting to—sales—and focus on what they care about most. Then, from within that context, consider the three elements that go into a winning SKO presentation:

  • Processes — Highlight the day-to-day sales activities that were meaningful (and not so meaningful).
  • Collateral — Make sure you have all the right materials including quotes, competitive intelligence, updated messaging, etc.
  • Morale — To make sure your audience doesn’t check out, find the stories that get people excited and encourage them to aspire to new heights. “I always think of the scene in the movie, The Patriot, when Mel Gibson’s character runs up the hill with the flag and turns the tide on the battle,” he says. 

At the end of the day, you want to educate your team with the facts and insights they need, but you also need to inspire them by showing them what’s possible when they put all that information and the available sales tools to work. If you accomplish that, everybody wins. 

For more inspiration, read Five Tips for a Successful Win-Loss Segment at Your Sales Kickoff to maximize the effectiveness and impact of your win/loss analysis. 

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