Shifting from Flywheel to Enterprise: How Atlassian’s Sales-focused Win-Loss is Helping Ensure Success in New Markets

Out in the world, Atlassian is a company on a mission to help unleash the potential of every team. Their tools like Jira, Confluence, Bitbucket, and Trellis help more than 250,000 customers worldwide become more nimble, creative, and aligned. 

Internally, Atlassian is just as committed to empowering their own teams. In addition to giving their teams access to powerful tools, the company also works hard to provide information that makes a difference. Atlassian’s win-loss program is one of the key ways the organization is helping sales, product, and other teams excel in a highly competitive market. 

Mike Dupuy, a Senior Product Marketing Manager focusing on how to bring new Atlassian solutions to market in the enterprise space, puts it this way, “win-loss is really important because it helps us understand the themes within each of our opportunities. This allows us to uncover anecdotes and customer stories about each sales success so that we can ultimately replicate that success with other customers.”

Mike recently joined us on the Blindspots Podcast where he shared how he and his peers are using win-loss to help Atlassian sell to enterprise organizations more effectively and successfully.

Program Catalyst — Use win-loss to Support New Sales Model and Overall Sales Success

Traditionally, Atlassian has primarily used a flywheel model to sell its products. This product-led approach focuses on engaging users directly, and delivering immediate value so that the product sells itself. There is little to no need for sales involvement in this self-serve model. 

However, as Atlassian begins to target enterprise organizations, the company needs to adapt its sales approach to accommodate selling to buyers who have a much more complex sales cycle and purchasing process. Rather than a self-serve approach that focuses on specific products and individual features and use cases, they need a more sales-led approach that meets enterprise buyers where they are and can provide more comprehensive and integrated solutions. 

Mike, along with other Atlassian product marketing managers, is helping build the story of how to move the company into the enterprise space successfully; and the win-loss program is an important part of that story. 

“One of our core motivations for working with DoubleCheck was to be able to expand our visibility into what actually takes place in the sales cycle, across multiple customers,” Mike explains. “win-loss has been critical, for example, in helping us get clarity on which personas we should talk to about certain use cases, solutions, and opportunities. It helps us identify the roadblocks we encounter, which messages are resonating, and which competitors are showing up in different types of deals.”

Two specific factors that further supported the launch of a win-loss program were a lack of CRM data and minimal insight into competitive intelligence. Mike viewed both of these areas as big opportunities to help sales succeed. “We wanted to make it as easy as possible for our sellers to manage deals and opportunities in our CRM,” he says. “But we just didn’t have as much data as we would have liked to be able to inform our sellers, and help them accurately identify which opportunities were strong, and which they should walk away from.”

On the competitive intelligence front, Mike hoped that a win-loss program would help him identify replicable winning patterns for the sales team. “We’re a pretty lean team, and we compete against a lot of different solutions,” he says. “We didn’t have insight from the buyer’s perspective about how they view Atlassian compared with other companies, or which products they look at against each other. It was important to be able to glean some of those insights to really flesh out our competitive analysis.”

Program Goal — Put Powerful Insights into Sellers’ Hands

Mike had two sales-focused goals at the outset, each of which was just one side of the same coin: generate more win-loss reports and build an effective way of getting report insights to sellers. 

When Mike first took over the program, there were already a handful of win-loss reports archived in an internal resource library for sellers. These reports gave salespeople an inside look at real-world deals that went either really well, or were lost. Mike’s first goal was to continue generating these reports, and to do it in such a way that they capture both sides of the equation—the wins and the losses. As he points out, there’s a lot you can learn from losses, so it’s important not to overlook them. 

Once he had these reports, the next step was to develop a way to get this critical information into sellers’ hands, both existing team members and new hires (as part of the onboarding experience). Mike understood right out of the gate that the success of the win-loss program depended as much on his ability to communicate with sellers as it did on his ability to capture win-loss data.

Success Key — Get Sales on Board

“We’re asking a lot from our sellers,” Mike says. “We’re asking them to make introductions to their customers, which means we’re asking for their trust.” To help earn the trust of Atlassian’s sales team, Mike made a big effort to communicate the win-loss program’s value quickly, and in a way that sales could immediately appreciate. 

“I found that the best way to earn trust and buy in was to go ahead and produce win-loss reports, and get them to our sellers so they could see how helpful the data is,” says Mike. Rather than developing an internal sales pitch, Mike skipped the dog-and-pony, and went straight to providing insights to help sellers in their day-to-day efforts. This real-world, first-person demonstration really helped get sellers on board. 

Mike further cemented seller support by nurturing a strong, collaborative partnership with the sales team. For example, he works closely with sales to identify customer candidates for win-loss interviews. After exporting all the opportunities for a particular quarter, he consults with the individual sellers to really understand which opportunities would be best for interviews or surveys. He also actively seeks sales input on whether it might be better to hold off on reaching out to a particular customer because an opportunity might still be on the table. Mike goes so far as to give sellers veto power on these decisions. 

“This program is ultimately about helping our sellers,” Mike says. “So having our sellers on board is super important, and having a strong partnership is really important.”

Use Cases — Begin with Sales, But Don’t Stop There

While the Atlassian win-loss program began—as most programs do—with sales in mind, Mike has found that the insights he captures from surveys and interviews have many valuable applications across the organization. 


The program’s primary benefit for the sales team is more effective enablement. In addition to providing the reports and generally giving sellers access to a library of success stories, Mike also focuses on highlighting specific, real-life examples that sellers can use in conversation with buyers. “It’s one thing to go into a customer meeting with slides and your standard pitch, but it’s another to be able to tell a relevant story about a specific customer,” Mike explains. “When you can show exactly how your solution impacted a similar organization, it really helps to build rapport with the customer and demonstrate experience. When you can pull out those stories, you are letting the prospect know that you’ve done this before—you’ve seen it, and you’ve had success with it.”

⛳ Product Marketing

As part of the product marketing team, Mike is responsible for creating the messages that appear on product web sites, pitch decks, and so forth. win-loss helps ensure that those messages are aligned with how customers are talking in the marketplace. “As marketers, we don’t want to create messages in a vacuum,” Mike says. “So, we love how our win-loss reports help us gain insight into not only who our competitors are for which use cases, but also the lexicon that customers use to describe the challenges they face, the solutions they’re looking at, and even details like which budget line item fits our product.” It’s powerful to create messaging that speaks to your product in the same language your customers use.  


Mike has also unearthed information that can contribute to roadmap discussions with the product team. “We can provide data on feature gaps, or on areas where our competitors have an advantage over us,” he says. “This information helps us inform our product direction based on real customer needs.”

️ And More!

As the program continues to develop, Mike continues to find additional use cases. One example he shared was how the program captured some customer frustration with the onboarding process. “Without the data, we wouldn’t have been so proactive about solving the problem,” Mike says. “We thought we were doing a good job, but the win-loss reports uncovered some gaps based on customer sentiment. Because we had those insights, we were able to remediate the issue quickly, and see immediate value from the program.”

Sharing Strategy — Share Broadly, But Make It Relevant and Motivating

To get the most out of the program, Mike is very consistent about sharing win-loss report insights broadly across the Atlassian organization. In addition to using company Slack channels, which are all public, he also maintains an internal Wiki on Confluence where there is a dedicated win-loss area to host all the reports. While the sales team is a primary audience for Mike’s various communication channels, there is also plenty of opportunity for cross pollination. For example, one of Mike’s product manager colleagues asked for an introduction to DoubleCheck after seeing some of the reports Mike had published.

Mike’s process for preparing and sharing reports has four components:

1. A weekly meeting with the DoubleCheck team to review reports, and highlight themes and patterns to incorporate into the reports. 

2. A full report that includes all the questions and data from the interviews (this version of the report is for internal team reference only)

3. A redacted report that is prepared specifically to share broadly across the organization 

4. The executive summary, which DoubleCheck provides

The reason Mike publishes only the redacted report has to do with his goal of helping sales and encouraging their ongoing partnership. “We want to make sure that everything we share motivates our sellers to participate,” he says. “We definitely give kudos to the team when there is positive information, but we’re not calling anyone out for a mistake they may have made. We don’t want to share anything that could cause sellers to hesitate about continuing with the program.”

While each individual report does a deep dive on a particular deal, the executive summary pulls back for a wider view of the overall picture. “We really love the way the executive summary aggregates the data, themes, challenges, and competitors across all our wins and losses into a single, hour-long presentation,” Mike says. “This helps us really hammer home where we win, and where we have struggled.”

Across all the reports, Mike acknowledges the benefit of having an unbiased third party like DoubleCheck conducting interviews. “Using a third party for win-loss helps you get feedback that you wouldn’t likely receive if you asked directly,” he says. “Customers seem to be a little bit more vocal, honest, and raw when they are talking to someone other than the vendor. That’s been really valuable for us as we try to uncover opportunities for improvement.”

The Bottom Line — Understand the Mission and Stick to It

Atlassian’s win-loss program helps Mike and his team get critical visibility into exactly what’s working and what’s not in the sales process, who the right personas are for various use cases, and how customers view Atlassian in comparison to the competition. And these insights help Atlassian make strategic decisions on everything from how to position against specific competitors to what messaging will work best on the website to which features the product team might want to consider for future development. 

win-loss research has been particularly important for Atlassian as they begin to engage in more complex enterprise sales that need more seller involvement than the flywheel model they have traditionally used to sell their products. 

Perhaps most important, throughout every stage of program development and implementation, Mike has been consistent in his efforts to get the sales team on board by collaborating with them in a true partnership. His North Star for success is his belief that the program’s ultimate mission is to help sellers, and he walks that walk by constantly demonstrating the real-world value of the program—delivering helpful reports that make a difference in the day-to-day success of the sales team. There’s a lot to be said for knowing your audience and giving them what they want. That approach seems to be working really well for Mike and the rest of the Atlassian team. 

To hear more from Mike about how Atlassian is using win-loss research, tune in to listen to the full episode

Want more episodes of Blindspots?

Join us in insightful conversations with win-loss leaders to help product marketers get a leg up on the competition through win-loss and churn analysis. Subscribe on Apple Podcasts, Spotify, Google, or listen on our website. 


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