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Bruce Kasrel, VP Research
Bruce Kasrel, VP Research Posted on November 4, 2022

Ask Me Anything: Salsify and Atlassian on Lessons Learned from Running a Successful Win/Loss Program

There’s nothing quite like getting the inside scoop from people who have already been there and done that. Our Ask Me Anything (AMA) series is a great opportunity to get a close-up, unedited look at how other win/loss program leaders are finding success. 

In this second event in the series, our guests were Caroline Doyle, Senior Product Marketing Manager at Atlassian; and Nathan Teplow, Competitive Intelligence Director at Salsify. We were joined by a great audience who asked excellent questions that really put our speakers to the test. 


Here are just a few of the highlights from the session.

Win/Loss Use Cases — Something for Everyone

The catalyst behind most win/loss programs is a desire to gain visibility into the sales process—what’s working and what’s not. However, most organizations soon discover that a win/loss program can deliver really valuable insights to a variety of groups, from marketing to product and beyond. 

For example, Nathan is using Salsify’s library of almost a hundred reports to inform a persona project. “It wasn’t part of our initial program scope, but our base of win/loss reports is one of the key resources we’re tapping into as we’re redoing our buyer personas and updating ideal customer profiles,” he says. “It’s really helpful because it’s language directly from our buyers. And we don’t have to go and conduct a bunch of net new interviews because we’ve already captured the input.”

At Atlassian, one of the main use cases for the win/loss program has been powering and supporting the competitive intelligence program. “Shockingly, we had no quantifiable information from the Jira sales team to be able to reliably identify the key competitors in our space,” Caroline explains. “So, the big thing for our win/loss program has been really fueling and backing up our competitive intelligence program, and helping us build that muscle.” 

In addition to its role with the CI program, helping inform personas, and providing guidance for how to build out solutions, Atlassian’s win/loss program also helps the product team prioritize their roadmap. “The product team has their inputs from customers, bug fix requests, new feature requests, etc. They have their own conversations with analysts and so forth,” says Caroline. “But we are able to bring some of the real verbatims from the win/loss program to back up the decisions they are making.” In a similar vein, Caroline also uses verbatims as evidence to support responses on analyst questionnaires such as those for the Magic Quadrant or Forrester Wave.

Win/loss insights can also help the marketing team make effective choices about where to place content or start conversations. Both the Atlassian and Salsify win/loss surveys include questions about where respondents seek information during the buying journey. Caroline points out that while this information can be helpful, it’s important to consider the persona you’re dealing with. “Depending on the persona, you’re going to get very different responses,” she says. “For example, executives who talk directly with analysts will consider those analysts a key resource. An evaluator, however—like a developer or Jira admin in our case—might be more likely to go to Reddit or G2 Crowd.” 

Win/loss insights also help Atlassian’s marketing team refine messaging, and can even help identify candidates for event-related engagement. “Customers who are willing to participate in DoubleCheck interviews are likely going to be willing to talk with us at a customer event,” Caroline says. “We share this information broadly within our marketing organizations to make sure we’re nurturing those relationships.”

Sharing Win/Loss Insights — Putting the Program to Work

One of the most important success factors for any win/loss program is how to effectively get the right information in front of the right people at the right time. Insights are only valuable if they are made actionable, and they only become actionable when they are put into context for a specific audience. 

Nathan figured this out really early on. “When we kicked off the program, and I got my first win/loss reports, I was so excited and wanted to share them with literally everyone,” he admits. “But I’ve learned to be really cautious about sharing an amazing insight in isolation with a bunch of people, and then having them run with it without having the necessary context.” He points out that it’s hard for people to absorb information if it hasn’t been tailored to their particular perspective, and getting information piecemeal can create a kind of whiplash when people make immediate assumptions without having the whole story. 

Over time, Nathan has developed a cadence that works well for him and for the various teams in the Salsify organization. “I rely a lot on the quarterly executive summary that DoubleCheck prepares on our behalf,” he explains. “I use that as the key cornerstone of the findings that we’re seeing across the board and across all our reports.” This ties into Nathan’s concept of thinking about win/loss both vertically and horizontally. Vertically, the program helps him dive deep into specific deals. Horizontally, he can identify trends and patterns that emerge after asking the same question over and over across many different accounts. 

From that foundation, Nathan has a process for identifying action items to share with specific teams. “I almost go on an internal roadshow,” he says. “I go around to the different teams and present some of the findings, breaking out and boiling down the key takeaways that are most relevant to each group.” It takes some manual work to create these tailored summaries for each group, but Nathan has found that this is the best way to reap the cross-functional benefits of the program. 

At Atlassian, Caroline also starts with the DoubleCheck reports, and then disseminates information from there. “We vet the DoubleCheck report pretty carefully via a pre-read and the executive summary,” she says. “And then we share the report on our Confluence page, and highlight it in our town halls.” Like Nathan, Caroline also works collaboratively with various groups, providing them with the appropriate insights from the win/loss reports. Her bi-weekly one-on-one meetings with the PMs and PMMs often include great discussions sparked by a particularly interesting insight from the reports. And she engages in similar conversations with the marketing team.

Win/Loss Analysis: A Foundational Pillar Of Any CI Program

Both Caroline and Nathan think of their win/loss program as a core element of their overall competitive intelligence program. “I lead our competitive intel program, and focus one hundred percent of my time on CI. A big portion of that is our win/loss program. It’s a key pillar,” says Nathan. “I consider it to be a pipeline of information about the market. Our marketing team is very in tune with our customers, with the people who are bought into our vision. The win/loss program is a great way to get a more neutral kind of market perspective of people who are just being introduced to the company for the first time, who aren’t customers or champions. It’s a great way to juxtapose the great feedback from the customer side with what prospective buyers are saying.”

Caroline also considers the win/loss program to be a critical part of overall CI efforts. “When I first started digging in, we had some big gaps in our understanding of why we were winning and losing, who our core competitors are, and how we want to position ourselves,” she says. “I use the win/loss program in a holistic approach that helps across multiple functional areas. It helps us improve the sales process, refine our messaging, address repeated complaints in the product, and so forth.”

As far as how Caroline and Nathan integrate win/loss with their CI programs, it’s all about good communication. 

As an Atlassian product marketing manager, Caroline does both CI and win/loss, so she shared the integration approach she used at Veracode. Her two-prong approach involved doing an internal quantitative analysis of Salesforce reports, and then layering on the win/loss report data. “The Salesforce reports were just hard numbers, but then we’d use the win/loss reports to color those numbers,” she explains. “The Salesforce data could help us identify areas to explore—like wins against a particular competitor—and then we could look at what the customer said in the win/loss report to see exactly what drove that outcome.” This approach helped build really strong battle cards by combining numbers with verbatims. 

Nathan is a team of one, but his position does roll up into the product marketing organization along with product-line PMMs, a director of PMM, and a few other roles like pricing and packaging. “I try to loop these folks in on any key findings from our reports that can help answer questions they have around trends, how business drivers change from one vertical to another, and so forth,” he says. “We also integrate on initiatives like the persona project, which the PMMs are spearheading. The report analysis I’ve done in Dovetail includes tagging that I can provide to the PMMs, giving them access to direct buyer feedback that’s really helpful.”

Measuring Program Success — Your Metrics Depend on Your Situation

We ended this great session with a question that always comes up in any conversation about win/loss programs: how do you define success? The answer: It depends. 

Since Atlassian’s program is still pretty new, the measure of success is simply to start building a better mousetrap. “When you haven’t been doing any sort of win/loss, aside from self-solicited stuff internally, it’s pretty easy to define success as ‘more than nothing’,” Caroline explains. “Over the last year, success for us has looked like just being able to answer some of the win/loss questions, have more resources for our sellers, and basically just providing another input that we can use to fuel our marketing collateral, product decisions, and so forth.”

Salsify takes a more traditional approach, tying the win/loss program to the competitive win rate. They also just kicked off a “sales confidence survey,” which assesses each sales rep on how confident they are going up against each competitor. “The plan is to run the survey on a six-month basis, so we can get a sense of whether confidence is trending up or down, and insight into how we can help them feel more confident when going against certain competitors,” Nathan says. 

Nathan also looks to anecdotal evidence when judging the program’s success. “I get pretty good feedback on the newsletters—people saying that they always make time to read them,” he says. “And after our first or second executive summary, our CEO actually reached out to my manager to say how awesome it is and to ask how we can do more, and expand the program. That was great validation that let us know we’re really onto something here.”


Get more great insights and inside tips from our AMA panelists.

Believe it or not, our panelists had even more to share in the full AMA session. You can tune in to hear the replay 👆 any time. 

And if you missed our first AMA with panelists from Seismic, Gong, and Bullhorn, you can watch the replay or read the summary article here

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