Your secret weapon: the closed-won interview (and how to use it to win your category)

All happy enterprise B2B SaaS deals are alike. Every unhappy deal is unhappy in its own way.

Leo Tolstoy (ish)

We product marketers love debugging. It’s just part of our nature. And there’s perhaps no better example of this in the enterprise B2B context than closed-lost analysis.

This involves talking to prospects that made it to a certain sales stage but didn’t sign a deal. The goal is simple: understand why the train went off the tracks.

The catch with closed-lost analysis

Closed-lost analysis is valuable, but there’s a problem: there are a million reasons a deal could get lost.

  • The SDR didn’t thoroughly qualify the prospect in the initial call.
  • A competitor undercut our price by 90%.
  • The AE picked her nose in a final presentation.
  • The economic buyer balked at the last minute because of the color palette of the in-app reporting. I’m exaggerating, but only slightly.

It’s a minor miracle that any deals close. A nearly impossible number of stars have to align for an enterprise B2B deal to get done!

So what should product marketers be doing? In our experience, it’s just as valuable – often more so – to study the happy path through closed-won interviews.

The who, what, and why of a closed-won interview

Closed-won interviews involve talking to customers who’ve just signed a deal. It’s that simple.

Why are they such a powerful tool? They help you identify common patterns – everything from personas to buying triggers to evaluation and process – among your best-fit customers. Sometimes it can feel like getting the “cheat code” to unlock a flood of qualified prospects.

These interviews are most effective if conducted by product marketing or success, NOT sales. (That way you maximize honesty and objectivity.) And they’re best if you do them as soon after closing as possible. That’s because you want them to walk you through their mental map of the market, the alternatives they considered, and their decision process – while they’re still fresh in their mind.

If you’re just getting started with closed-won interviews, you might consider some of the following questions:

  1. What problem were you trying to solve?
  2. Why did you choose our solution?
  3. How do you plan to use our product?
  4. What was your decision-making process like?
  5. Who else was involved in the decision?

You’ll quickly start identifying common threads – around your best fit customers, the use cases that are driving urgency and intent, and your customers’ perception of your uniqueness. These are all gold as a product marketer.

Three questions you’re probably not asking, but should be

The questions above are a great jumping-off point. But if you’re looking to get even more “bang for your buck” from your closed-won interviews, consider asking these three non-obvious questions.

Here are the questions – and what actions you should take based on what you learn.

“What almost made you walk away?”
  • Why it works: this question reveals hidden weaknesses in your offering or sales process. More importantly, it highlights what ultimately kept the prospect engaged.
  • Action item: Rewrite your sales playbook around your prospect’s decision journey, not your sales process.
  • Example: You discover that prospects almost walked away due to concerns about implementation time. In response, you create a new “Quick Start” program, restructuring your onboarding process and adding it as a key selling point in your playbook. This addresses a critical customer pain point early in the sales process.
“Which competitor came closest to winning, and why didn’t they?”
  • Why it works: This uncovers your true competitive edge – which often differs from what you think it is.
  • Action item: Adjust your product roadmap to double down on the features that are actually closing deals.
  • Example: Through closed-won interviews, you learn that your API’s flexibility was the reason you edged out a major competitor. Despite this not being a focus of your current development, you pivot to prioritize expanding API capabilities in your next two quarters, potentially opening up new integration-focused market segments.
“If you were pitching our solution to your board, what would you say?”
  • Why it works: This gives you the customer’s perspective on your value proposition – usually clearer and more compelling than your own.
  • Action item: Craft a new positioning statement based on why you’re really winning – not why you think you should be winning.
  • Example: Your original positioning focused on cost savings, but closed-won interviews reveal that customers are actually choosing you for speed to market. You reposition from “The most cost-effective project management solution” to “Launch projects 50% faster with our streamlined workflow.” This aligns your messaging with the actual value customers are deriving, potentially attracting more best-fit prospects.

In my experience, these often lead to the juiciest insights – with clear next steps to take to improve marketing and sales results.

The bottom line

There are a gazillion ways to lose a B2B enterprise deal; you won’t have much luck improving your strategy if you only focus on the negatives. Focus instead on what you can learn from closed-won deals – with an eye to non-obvious questions that can yield product marketing gold. If you’re asking these questions, it’s only a matter of time before you nail everything from your ideal customer profile to your killer use cases and differentiation.

Jordan is a Managing Director at Blue Seedling. You can find him reading medieval literature, running, or helping B2B startups with go-to-market strategy.

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