📈 Scaling a Win Loss Program From Nothing

I started by building a business case for a formal customer interview program and securing buy-in from the sales leaders. I positioned the work as a way to improve the sales motion—not evaluate individual sellers—and explained that the interviews would not put active deals at risk. That trust was essential because the program depended on sales access to customers and prospects.

We chose to send interview invitations for every deal rather than rely only on Salesforce data. Our reasoning was twofold: Salesforce information was not always complete or accurate, and prospects and customers were more likely to be candid with an outside interviewer than with the salesperson involved in the deal. I segmented the incentive by ARR, offering larger gift cards for higher-value opportunities, and established a process for targeting both wins and losses. As the program developed, I added a Salesforce button that allowed sales to opt specific opportunities out when necessary.

The first interviews surfaced two important patterns: UI/UX was a major reason we lost, while trials were associated with more wins. I shared those findings with the product and solution consulting teams. Product used the feedback to modernize the homepage, while solution consultants began pushing trials more deliberately in the sales process.

Over time, I also identified a structural problem in the operating model: relying on internal tools and other teams to make changes made it difficult to move quickly, iterate, or run A/B tests. Excel and Smartsheet were not giving me the analysis I needed to identify trends efficiently, which became an important input into the next stage of the program.

I started with the tools we already had, then changed the stack as the interview program grew.

• Gainsight handled interview outreach and surveys. It let me contact customers and prospects through a repeatable process rather than manage invitations manually. Sendoso delivered the gift-card incentives, which we varied by ARR grouping; higher-value opportunities received larger incentives.
• I began analyzing the responses in Excel, then moved to Smartsheet as the volume increased. Both helped organize the data, but neither gave me the speed or analytical flexibility I needed to identify trends and iterate quickly.
• Gong recorded the interviews, giving us a reliable record of what customers actually said, and Calendly later simplified scheduling. These removed coordination work from the process.
• As the program and company grew, relying on other teams to make changes became a bottleneck. We purchased Clozd so I could run the program myself—from emailing through analysis—instead of repeatedly asking colleagues to adjust internal tools. That was the most important change because it restored my ability to move quickly and test improvements.

AI was not part of the original program because it was not available in the tools at the time. Clozd now includes AI, but I have not treated it as a substitute for judgment: the value still comes from asking the right questions, interpreting the feedback, and connecting it to decisions. If I were building the program again, I would choose an integrated platform earlier rather than stitching together tools and depending on other teams.

Since launching the program in 2022, I have completed more than 215 customer and prospect interviews, consistently meeting the target of 15 interviews per quarter across wins and losses and presenting findings every two months. The interviews also contributed to $175,000 in win-back revenue: opportunities we interviewed after losing and later won back. I treat that as influenced revenue rather than claiming sole attribution.

The program changed decisions beyond the numbers. Customer feedback showed that UI/UX was a major loss driver, which led the product team to modernize the homepage and prompted the AI team to work on product improvements. Feedback also showed that trials were associated with more wins, so solution consultants began using trials more deliberately and we continued working with sales on value selling.

This year, from January onward, our email cadences have averaged a 64.8% open rate and a 9.2% participation rate. The most significant lesson learned is that a repeatable listening process adds value only when its insights influence product and sales decisions, not when the interviews remain merely as a research archive.