Standing up a win/loss interview program is an essential step in a company’s maturity, and it should happen sooner than many people think.

Win/loss interview programs are one of the most important ways to gather actionable market intelligence. Yet many organizations don’t have a consistent interview process in place, either because they’re not convinced of the value or because they believe sales data is enough to understand the market and drive potential growth.

In fact, the interview program is a separate but complementary activity that’s led by the product team and delivers a depth of market insight sales data can’t achieve by itself. In this GrowthBit, I’ll explain why I believe every product company beyond the early startup stage needs a robust win/loss interview program as a means to mature and scale their operations.

What is a win/loss interview?

A typical, sales-driven win/loss program collects and analyzes quantitative pipeline data, including funnel analysis, sales cycle, and close rates by segment. This data is valuable, but if the program doesn’t go beyond these metrics, you’re missing a big part of the picture and you run the risk of making decisions based on the opinions of your sales reps or most recent customers.

Win/loss interviews help you round out the picture. Along with tools such as net promoter scores (NPS), customer satisfaction scores (CSAT), flash surveys, analysis of support tickets, UI focus groups and advisory boards, win/loss interviews help the company refine product-market fit at scale. They collect data from a broader cross-section of your market — including those who buy, those who stall out and those who go to competitors — in order to seek out the “why” behind the buying decision.

Essentially: why do you win or lose? Why does a customer buy your product? Why don’t they? If they choose a competitor, why is the competitor’s offering more compelling? That data is then used to improve R&D, refine product-market fit and drive growth.

How to stand up a win/loss interview program

Standing up an interview program is an essential step in a company’s maturity, and it should happen sooner than many people think. Here are the key components.

Assign an interviewer. Product management is well suited to this task because they’re furthest from the sales process and typically do not have a relationship with the buyer. This helps ensure the question phrasing and notes collected are unbiased.  Third-party firms can also be a good option due to their independence, although using one does not help build this core competency within your company. Sales, marketing, and customer support often have a history with the buyer, which can negatively influence the quality of the data. As such, I would not recommend customer-facing staff for win/loss interviews.

Centralize the data. Collect quantitative and qualitative interview data by creating discrete picklists in the CRM for each opportunity along with free-text notes. Having a common repository also gives easy access for sales, marketing, product and other departments who may make good use of this market intelligence.

Build reports. Aggregate picklist responses to identify trends, summarize free text to capture more nuanced insights and consolidate both types of data into quarterly reports.

Standing up a win/loss program is an important step in becoming a market-driven organization.

Benefits of launching win/loss program

I believe the ROI for win/loss interviews is significant. It enables the organization to quickly summarize why they win and lose deals by vertical market, segment, customer size and other dimensions.  One recent study from 2020-2023 showed that win/loss interviews improved close rates by 23%.1 This is strong evidence for the value of this information across the organization, from R&D to the go-to-market functions.

Here are three valuable outcomes you’ll see by launching a win/loss program.

Evolution to Market-Driven Product Development: How?

Product development for startups tends to follow one of three patterns: engineering-driven, sales-driven, or customer driven. These are all important sources of product input, but as companies scale, overreliance on one model can lead to problems. Standing up a win/loss program is an important step in becoming a market-driven organization.

Incorporating the full market perspective into the decision-making process enables the organization to see beyond the limitations of internal perspectives and customer expectations and start predicting and capitalizing on longer-range market and competitive movements.

Generate actionable insights

Win/loss interviews collect in-depth, qualitative data capable of delivering market insights that you can apply directly to your most impactful growth levers. They probe the motivations and perceptions of the people who become your customers (and those who don’t), yielding deep, insights that help you peel back the data and understand the context. And you can slice and dice that data by region, industry segments or any other variable to drill down, identify your most rewarding sectors and refine the positioning, messaging and feature sets—and then conduct outreach accordingly.

Make defensible R&D decisions

A win/loss program is an essential research tool that helps your product team build a product roadmap based on a market analysis, which in turn allows them to articulate the value of R&D spend. That spend tends to grow as the company grows, and as those costs become more significant, boards start to scrutinize them much more closely. Commissioning a market study may be prohibitively expensive, but a win/loss program can be launched for little more than the cost of an associate product manager’s time.

Without win/loss data, this company may have made an unwise decision which could have negatively impacted growth and opened the door for competitors.

A real-world example

A digital training company offered an extensive library comprising thousands of courses, which cost millions of dollars per year to maintain. Yet user data showed that 90% of completions were on a tiny fraction of the courses.

This prompted the question: why not drop the unpopular courses, focus on the top few, slash costs and improve profitability? There was some logic to it; however, win/loss interview data revealed that “breadth of content” was the top purchasing driver among buyers.

Not unlike fitness centers that entice members with an impressive array of equipment, even though most of them end up using just a small subset, this training company needed an extensive training catalog to stay competitive. Without win/loss data, this company may have made an unwise decision which could have negatively impacted growth and opened the door for competitors.

Here’s the bottom line.

I recommend most product-oriented software companies with annual revenues of $10 million or more to establish a win/loss interview program because it’s among the lowest cost and highest value activities for gathering market intelligence. Win/loss interviews can help generate the kinds of insights and validation that help grow market share, ensure product/market fit, and guide the most targeted R&D spend, all of which helps companies scale faster.

  1. “Clozd 2023 State of Win/Loss Analysis Report,” Clozd, 2023,