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Bruce Kasrel, VP Research
Bruce Kasrel, VP Research Posted on August 10, 2021

Lessons from Leaders - Fuel your competitive intelligence efforts with win/loss program insights | Podcast

How can you best leverage win/loss program insights to drive competitive intelligence value? This was just one of the questions I had the opportunity to ask in a recent DoubleCheck Research Win/Loss Peer Forum Fireside Chat with guests Paul Senatori, Director of Competitive Intelligence at Sitecore, and Carlo Cadet, Senior Director of Product Marketing and Content at BitSight. As part of our peer forum series, this session gave us the chance to share experiences and best practices on several CI topics.


In his role at Sitecore, Paul is responsible for and intimately involved with all CI activities on a global basis. His team includes an analyst, and he reports up through the product marketing organization. Similarly, Carlo’s product marketing and content role includes responsibility for CI, and his team includes another person who spends approximately half their time dedicated to CI. 

Over the course of our conversation, we talked about which CI sources they rely on most, which CI deliverables are most important to the sales team, how they adapt CI efforts when working with non-sales stakeholders, and—of course—how to leverage win/loss in CI efforts. 

Top CI Sources – Pulling It All Together

Tapping into and balancing multiple CI sources is a key element of any successful CI program. Sources can be internal, third party, or from your network. For example, Carlo harvests quite a bit from field insights, using both a Slack channel and a competitive email alias to collect and aggregate information. He finds that the field is also a good channel for capturing valuable primary source data like quotes, sample product, and sample reports. 

Carlo also uses some third-party sources. He is particularly pleased with the search and tracker tools in Gong, which he uses to record U.S. sales calls. Paul uses Klue to curate all his competitive content and assets, including battle cards. The Dovetail platform that houses his DoubleCheck win/loss data provides him with a qualitative repository for raw competitive data (including things like recordings of competitor webinars), and he uses two vendors for secret-shopper activities and other outbound research. 

“We also leverage pre-sales and sellers whenever we can,” says Paul. “We are a team of two, but including these folks, we’re a virtual team of about two hundred.” Paul considers pre-sales and sellers to be an invaluable source of CI, especially when they have previously worked for one of their competitors and can provide insight into exactly how that competitor is positioning themselves against Sitecore. 

Paul also taps into Sitecore’s global partner network. “We’re a very partner-centric organization with 100 to 200 partners who operate in our competitors’ camps,” he says. “That can work for us and against us. It gives us a view into how each partner interacts with specific competitors, but they don’t share a lot because they don’t want to burn any partner relationships.”

Other sources we talked about included international events (which Paul noted are a great opportunity since most competitors don’t expect anyone will be monitoring that activity) and secondary resources like LinkedIn. 

High-impact Deliverables – Giving the Sales Team What They Need Most

Unsurprisingly, both Carlo and Paul cite battle cards as the go-to “competitive enablement” deliverable they provide to their respective sales teams, though they each extend the value of this key deliverable differently. Carlo complements battle cards by building a dedicated online course that serves not only the existing seller team, but is also a very effective onboarding tool. Paul turns each original report into a single slide—something a seller can absorb in three minutes or less—and a corresponding three-to-five minute podcast. “We now have a catalog of more than eighty slides that our new sellers and pre-sales people can browse through,” Paul says. “And they are all structured exactly the same way so that a seller can immediately recognize fields and key takeaways about headwinds, tailwinds, and other information.”

Another deliverable that Carlo ranks high is deal-by-deal support. “On demand, we help craft a targeted response to a particular prospect,” he says. “This usually involves real-time curation of existing data.” 

In addition, Carlo runs a monthly forum with sales management and a few other invested parties. “My goal in these meetings is to drive a two-way dialog about the data. It’s an opportunity for leadership to tell me where they want me to focus and which new assets they want me to deliver.”

Paul also runs regular meetings, including a monthly win/loss call and quarterly reports for the executive team. The monthly win/loss calls used to focus primarily on drilling down into the reasons behind lost deals; but Paul is transitioning that format to include wins to make the experience more positive. The quarterly reports for the exec team help secure funding from the CMO, CRO, and CEO to continue doing critical CI work. 

CI for Other Stakeholders – Spreading the Value across Different Functions

While the sales team is the primary target for CI, the marketing and product teams can also learn a lot from CI content. Paul and Carlo agree that the marketing team is important because, as Paul puts it, “If we can affect the story and the narrative around our products, [then] that trickles down to the sales organization through enablement material and training and onboarding.” And the CMOs at both Sitecore and BitSight count on win/loss reports for all the QBRs and quarterly reporting.

While the product team is usually a step or two removed from the front lines, CI can still impact their work. For example, at Sitecore, Paul was able to quickly pull together a report summarizing mentions of a specific set of editing and authoring tools that had been fairly low on the product team’s priority list until competitors started improving corresponding tools in their products and positioning them as a key differentiator. The CI helped the product team assess how prominently that particular feature ranked as compared to other evaluation criteria. 

Carlo does something similar, “We complement our interviews with online surveys that compare the importance each prospect places on different features and/or attributes of the company relative to how they rate our offering. So if, for example, someone thinks the UI is extremely important and they rate us very low, that’s a conversation opportunity with the product team.”

In addition to sales, marketing, and product, CI can also come into play with other groups. For example, the legal and procurement teams can benefit from a better understanding of how customers perceive the transactional aspect of a deal. And the CI team is also a natural channel via which to feed opportunities to the customer marketing and customer reference groups. “As part of our interviews, we ask the customer whether they’re open to being a reference,” Paul says. “We deliver twenty or so opportunities per quarter.”

Win/Loss Insights – Increasing the Value of Your CI

With all the different elements that go into CI, it’s important to understand how to get the most value out of every effort. When it comes to win/loss program insights, sales enablement tops the list of how to best put them to use. In addition to ensuring the sales team is fully aware of the primary competitors, win/loss insights deliver critical, up-to-date deal feedback that gives the sales team an edge and drives greater efficiency in their day-to-day activities. 

Win/loss insights also help sellers see the broader picture. “Sellers are operating in just their own territory, region, and vertical,” Paul explains. “They don’t see across the map how deals are won or lost against competitors.” Being able to share insights from all across the organization helps ensure that everyone is benefitting from everyone else’s experience and those lessons can be applied universally. 

And, as we already discussed, win/loss insights can help in non-sales areas as well. “I also fold in conversations with regards to both product strategy and product pricing in particular,” Carlo says. “And from a product marketing perspective, I take a very close look at the business drivers/compelling event data we collect to see how it informs our messaging.”

Win/loss program insights also fuel most competitive assets, including battle cards. “Without win/loss insights, we can get very myopic in terms of our internal view of how the market is operating and how products are being differentiated,” Paul says. “Through win/loss interviews, customers can right-size that for us, so we can align more closely with their actual challenges, and get a more accurate read on which story is resonating with them.”

And from a competitive perspective, win/loss program insights detail which competitors are winning deals, and which are not. They also provide specific information about if and how competitors are positioning themselves against your product, and how customers perceive the competitive dynamics. “Unless you talk to your customers, you’ll never know whether a particular competitor is bringing you up or not,” Paul says. “And you won’t know whether the way you talk about competitors is effective or a turnoff.”

Optimal Win/Loss Report Quantity – Getting Started

During the live Fireside Chat, we got some great questions from the audience. One was how do you figure out the right number of reports to create a successful win/loss program?

Paul and Carlo both found the sweet spot by triangulating several key factors including budget, number of deals per quarter, and how much your organization can absorb and translate into relevant insights. 

Sitecore does approximately 20 reports per quarter, and they arrive at that number by starting with roughly 150 to 200 qualified deals, which they then narrow down to about 80 to 90 to hand off to DoubleCheck for initial calls. From there, the list is whittled down to approximately 30 to 40 that are truly qualified. And then there are usually about 10 customers who drop off. 

Paul points out that the number is fluid, and changes as a company evolves. Sitecore started with 15, moved up to 20, and is currently increasing to 25. In Sitecore’s current case, the increase is driven in part by the addition of new, smaller competitors that have come into play as Sitecore has acquired some new companies. 

At BitSight, Carlo is planning to double the number of reports per year, from approximately 30 to 60. He’d love to do more, but is constrained by the absorption rate into the organization. “It’s almost a choke point trying to distribute 15 pages or even the summary alone,” he says. “But it’s important to get up to a representative number, otherwise it’s purely anecdotes.”

What’s Next – Questions to Ask About Your CI Efforts

The conversation with Carlo and Paul was really informative, and it also surfaced some key questions that can help an organization hone in on how to optimize overall CI efforts, and how to identify opportunities to successfully leverage win/loss program insights to drive even more CI value:

  • Are you taking full advantage of all the CI sources available? Are you missing out on any internal sources within your sales organization or any other functional area? Do you have the ability to use third-party tools and sources to expand, automate, or aggregate and organize your CI material?
  • Are you providing your sales team with the most effective CI assets? Are your battle cards and other materials designed around the sales team’s needs? Are there other formats or media you could use to present key information more effectively?
  • How are you nurturing and evolving the CI conversation within your organization? Are you involving players from multiple areas like marketing, product, and others? How is your leadership team involved? How does your CI deliver value for these groups? Does the dialog you create foster two-way sharing of ideas, needs, and insights?

For more inspiration, listen to the Blindspots episode on Discovering a Best-in-class Competitive Enablement Program featuring Jason Smith, Founder of Klue, who offers great insights about what goes into a modern, top-notch competitive enablement effort, and more. 


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