Measuring the Progress of a Challenger™ Transformation

Measuring the Progress of a Challenger™ Transformation

As we approach the 10-year mark since The Challenger Sale was first published, we are working with clients at every stage of their Challenger transformation, whether that be early-phase communications and program launch or steady state execution after multiple years of sustained reinforcement. The common question that ALL our clients continue to ask is this one: How should we think about measuring progress and documenting ROI on the investment?


I’m a big fan of the following quotation from Frances Hesselbein, former CEO of the Girl Scouts of America and a Presidential Medal of Freedom recipient: “Culture does not change because we desire to change it. Culture changes when the organization is transformed—the culture reflects the realities of people working together every day.”

You often hear people reference organizational culture as a slow-moving Freightliner that changes direction only in small increments at a time. However, for many sales and marketing organizations, a shift to the Challenger sales methodology represents a true cultural shift. If you are watching closely and the organization is truly transformed, there will be clear signs along the way, both positive and negative. We would point to three major points of change in any Challenger transformation:



One of the first and biggest changes will be the conversations your sales teams are having with customers. Hopefully, if marketing is along for the ride, this will also include different digital “conversations” you have with the market to represent a new point of view. Ask your sales managers if those conversations are different today than they were before you started. Ask your customers, too; they should notice it very early. Are you hearing conversations centered around business issues (e.g., productivity, risk, revenue, cost) or products and features?



The Challenger methodology, for most organizations, represents a shift toward a more judgment-oriented selling approach. It is less focused on process alone and more focused on leadership, sales, and marketing collaborating to find new ways to generate demand and move deals forward. Our research suggests that helping create that judgment-oriented organization (i.e., smarter, flatter, less top-down, less compliance-focused, more creative) will actually amplify the results of Challenger for your team.



So let’s get to the bottom line: What type of ROI should you expect? In a recent ROI study, we worked with thousands of individual sellers (close to 5,000 across 60 active clients) to see how many deals they were able to advance after applying a Challenger strategy. The median impact we’ve seen is a 15x payback in top-line revenue directly attributed to Challenger moving stuck opportunities forward. In fact, 46 percent of these stuck opportunities actually advanced within 60-90 days post-workshop. We’ve also documented improvements in cycle time and conversion rates because the Challenger sales methodology creates more urgency for customers to take action. Are your deals moving any faster through the funnel?

So, whether you are on day 1 or 1,000, consider the change that will take place across your organization. How do you expect that change to manifest over time? Where (and from whom) will you see roadblocks or points of friction along the way? Who will be your champions? Are your leaders prepared for the change? Have you considered the metrics that are most important to track over time? Make sure to establish a “change dashboard” to measure and help manage progress and ROI along the way, and revisit that dashboard every so often to make sure you are laser-focused on the changes that are right for your organization and your customers.

Visit our website to connect with our team and start a conversation to learn more about measuring the progress and ROI of your Challenger transformation.

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Additional Resources: 

Webinar Replay - "Measuring the Progress of a Challenger

Infographic - The Challenger Impact Study