• PMM Camp
  • Posts
  • #60: Win-Loss for PLG and Hybrid Companies

#60: Win-Loss for PLG and Hybrid Companies

How to build a non-traditional win-loss program

Win-loss analysis is often considered an enterprise sales activity. After all, it’s the process of analyzing why a sales deal was won or lost.

There’s a ton of content and conversation online about how to build an enterprise sales win-loss program. But, this doesn’t mean it’s not applicable in a self-serve or hybrid motion either. I actually think it’s a tactic that’s super under-utilized in these types of companies.

I’ve spent most of my career in companies with a hybrid go-to-market motion — meaning the majority of customers come in through a free trial while a small portion of customers speak to an inside sales team. And, I’ve built many effective win-loss programs.

Today, we’re going to dig into how to incorporate win-loss practices in a non-traditional way.

Let’s get into it 👇🏻

Uncover the real reasons you win or lose deals with Clozd, the sponsor of today’s newsletter.

Wondering how to apply all of those juicy insights post-interview? Clozd recently launched Win-Loss 101—a special (and free!) toolkit built specifically for product marketers who want to leverage the power of buyer feedback to …

  • Improve product positioning, messaging, and differentiation

  • Influence product strategy and roadmap

  • Drive revenue growth

These resources provide a quick and thorough overview of how you can use win-loss insights to develop a clear picture of how your buyers perceive your product—and exactly why they can (or can’t) justify purchasing it.

Check out the Win-Loss 101 series today for free.

Win-Loss for PLG

Let’s start with a shared definition of win-loss. Win-loss is the practice of capturing and analyzing feedback about why you win or lose sales opportunities customers. Effective win-loss analysis helps you uncover the truth about why buyers make their final purchase decisions.

A formal and rigorous win-loss analysis program enables better segmentation, product strategy choices, and sales enablement. Those that take a more comprehensive approach have seen a 15–30% increase in revenue and up to 50% improvement in win rates.


Now, it’s easy to see how this applies to large sales deals. BUT, isn’t it true that all product marketers want to know why their prospects and leads are converting or not? Converting on a free trial is still considered a purchase - the desired outcome is the same.

Here’s how I’ve built win-loss programs at non-enterprise companies.


When you’re dealing with thousands of trialers a month, it’s impossible to speak to a meaningful portion of converted or churned prospects. This is why many assume win-loss doesn’t work for PLG. But, we just need to give it a reframe.

The key to a scalable win-loss program is to go beyond phone calls and apply a multi-channel approach. Data shows that more companies are leaning into this — 75% of companies use at least three different feedback channels.


Automation is your friend. Implement automatic feedback collection wherever and whenever possible.

When a trialer cancels their subscription, send them an automatic survey with a few simple questions about why they chose not to continue. Make sure to ask if they are choosing another product instead (and if so, which one). If cancelling a trial requires action in-app (an opt out trial vs an opt in trial), you can also collect this data during the cancel flow. Use all of this cancellation data to calculate which competitors you’re losing to the most and to identify the top reasons trialers didn’t purchase.

But, don’t forget about converted (ie. won) customers too. I like to approach this group the same way we would with NPS — randomly sample a certain number of newly converted customers each month. This will help you identify the reasons for purchase, which can be contrasted with the data you collected from cancellations.


Build a rubric to determine which types of customers will qualify to receive an official win-loss call. Typically, this list might include prospects who interacted with a sales rep or self-serve customers who are in a high priority segment.

Determine your team’s capacity to conduct win-loss calls and set a target for a specific number of interviews a month. If you don’t have internal capacity to complete these calls, you can consider working with an outside customer research consultant or a vendor like Clozd.

Layer in the learnings from your win-loss calls with the learnings from your surveys to get the full picture.


If you’re working in PLG or hybrid, your company may not be as familiar with the concept of win-loss. This means you’ll need to make sure you socialize the concept with leadership and other key departments before rolling out your program.

It’s also important to build in recurring rituals to surface the insights you’re discovering. I recommend you do this on a quarterly basis at a minimum (depending on how quickly you can identify trends). If your company already has a monthly Voice of Customer meeting, this can be a great forum to bring this topic for discussion.

Have you implemented a win-loss program in a non-traditional way? If so, I’d love to hear your strategies. Just hit reply and send me a note.


📚 Reading List: Here’s a handy resource from the Product Marketing Alliance on how to conduct win-loss interviews.

🎧 Playlist: While you’re in a competitive headspace, check out my friend Andy’s podcast Healthy Competition.

Until next week,

Tamara Grominsky

Ready to build a high-impact career? Here’s a few ways I can help:

  • Build connection and grow your career alongside 150+ other PMM leaders. Join the waitlist for PMM Camp’s private community, the only community built for (and by) PMM leaders. New spots open up March 18.

  • Craft your own personal positioning statement in 30 minutes or less. Take my free mini course and learn how to identify and communicate your “secret sauce” as a PMM.

  • Need a product marketing mentor? Book a 45-minute 1:1 session with me to cover any topic of your choice.