What insights should a good win-loss program uncover?

04/06/2026Learn

Win-loss should be a goldmine of information about your customers, competitors, product and GTM processes. But if you’ve never done consistent win-loss – or you’re feeling a bit underwhelmed at what your win-loss program is delivering – it can be hard to know what good looks like. This article lays out, in clear terms, the insights that win-loss should surface on a regular basis.

1. Customer Pain
2. Customer Process
3. Competitor Tactics
4. Competitor Product
5. Commercials
6. Your Product
7. Sales Experience
8. Customer Success Metrics
9. Conclusion

Customer Pain

Every single SaaS firm in the world – let’s take it a step further and say every single B2B firm in the world – needs to hear this directly from their customers. It shapes the entirety of your Sales, Marketing and Product functions; namely, what problem are you trying to solve for your customers? You may think you already know, but you’d be surprised how much more nuance there often is in this question when you start speaking to buyers regularly.

In win-loss interviews, customer pain should be the very first question asked, before you even start discussing why the deal was eventually won or lost. In interviews, it can sound like this:

• “We knew we had to go to market for a new solution when….”
• “We saw internally that…”
• “It was costing us $$$ in time, lost productivity, lost information etc etc….”

These kinds of responses should almost always be followed up with questions about how the customer knew the problem your product solved was a real problem. For instance, what kind of data or alert system has the customer got set up internally? How often do they take the pulse of things in certain areas of their business?

All this information is crucial because adopting customers pain language and metrics is the way you draw them into your pipeline, and the way you communicate the value of your offering so that it makes sense to them.

Customer Process

Everything from pipeline generation to Account Based Marketing (ABM) to your sales process, should be aligned to how the customer wants to buy. The more you know about this process the better, and the better your chances of accelerating time to close.

Customer buying processes can vary enormously between different types of solutions, to different buyer personas to different segments (SMB and Enterprise will be very different) and verticals. But all customers have a process – no matter how long or short.

In win-loss interviews, it can sound something like this:

• “We had a buying committee internally, where we whittled it down from six solutions to two.”
• “We had a shopping list of features we knew we needed from a new product.”
• “We surveyed employees internally to see which features they currently used the most, and what they felt was missing.”
• “We had a big excel spreadsheet on our needs, which was weighted according to priority. After each demo, we gave each vendor a score.”

From then on, your win-loss interviewer should be asking questions about the chain of purchasing authority, procurement involvement, contract redlines etc.

And, of course, it’s vital to ask how the customer came across X software or solution in the first place. Was it a simple search, or an analyst report, or a personal recommendation? Win-loss should help you understand how you became a key potential vendor for your customer, and the areas where you have credibility.

Competitor Tactics

One of the most-asked-for things I hear when it comes to win-loss and Competitive Intelligence is “I would love to know what our competitors say about us.” This is because buyers will almost never look at just one vendor as a potential provider; this is even more the case when you’re selling to buyers with budgets in the six figures.

While your number one priority should be solving customer pain, it’s a fact that the claims competitors make about you, or how they position versus you, does have an impact in the eyes of the customer. And you need to know these things, so your sales team can counter and your Product Marketing team can differentiate and debunk, or even attack when the opportunity arises.

In interviews, it sounds like this:

• “Competitor A told us that your adoption rate is lower than theirs, and that you require a lot of IT support to implement.”
• “Competitor B told us that you didn’t do as well as them on the recent analyst report, because of…”
• “Competitor C pushed the discussion towards X use cases, because they said that’s where they’ve solved the same problem for companies similar to ours. They showed us X data.”
• “Competitor D sent us some case studies of X, and put us in touch with X customers of theirs for a reference.”
• “The demo Competitor E did for us revolved around X. They had this whole narrative around ….”

Good win-loss interviewers should ask for specifics on the proof competitors provided to back up their claims. This information becomes the root of all your battlecards and playbooks, as well as all your sales enablement sessions.

Competitor Product & Roadmap

You probably have a good idea of what features your competitors’ products have, or the main areas of similarities or differences – even if you don’t have a total and full picture of features.

Win-loss should help flesh out this picture and give you a strong idea of the features your competitors believe are USPs, or which move deals for them. It should also give you a solid insight of your competitors’ roadmaps and future-facing product priorities. This is absolutely critical information to give to your Product teams.

In win-loss interviews, competitor product and future features can sound like this:

• “They really pushed X feature. They talked about it a lot in the demo and saying it was unique.”
• “We liked the idea of X feature, but it only came as an add-on so that was a bit disappointing.”
• “They showed us their roadmap for the next 18 months. It had agentic AI for X coming next quarter, and they said a lot of customers have been asking for…”

Commercials

Competitor pricing is a very tricky thing to get, because it’s not in the public domain. I’ve seen list prices be discounted by 50% or more by vendors keen to secure a certain logo, or to lock in a customer for longer periods. If you don’t know what your competitors are charging, you have no chance of being competitive yourself, or (if relevant) being able to articulate why you are priced at a certain level or structure.

Some customers will straight-up tell you what they were quoted by others. Other interviewees are more cautious, but chances are you’ll almost always get some very strong indications. Collated over time, these compound to make an excellent bank of up-to-date intel which your board and investors will love you for, and which your Deal Desk or Price-to-Win function will use to close important business.

In interviews, it sounds something like this:

• “You were about the same on licenses.”
• “I can’t give you exact figures, but the implementation was a sticking point. You were about 45% more expensive than competitor Y.”
• “Competitor A offered to spread the cost of the implementation over the lifetime of the contract. That meant we didn’t have the huge upfront cost.”
• “Competitor B offered us an additional 10% discount if we signed by the end of the quarter.”

Notice that this is not always the cost of licenses. Buyers needs to take into account implementation and change management costs into an overall picture of Total Cost of Ownership (TCO) vs ROI.

Pricing is certainly far from the only reason deals close won or lost – but it’s a substantial lever at your and your competitors’ disposal to get deals over the line.

Your Product

Clearsighted’s customers consistently report that detailed technical and product insights are one of the areas where many outsourced win-loss providers and agencies struggle to obtain good insights. This is because getting to the heart of product decisions requires a more skillful interviewing approach.

You need detail. What you don’t want is: “we thought the other vendor’s UX was better than yours.” That is not enough insight to act on.

Instead, your win-loss program should uncover nuances like: “it was just too many clicks, and the central dashboard was too difficult to navigate. To be able to see A and B view at the same time was critical for us, because we found that a lack of comparison data before…..” Often, concerns about UX are closely tied to fears about implementation, training or change management, or they can even relate to perceptions about your brand.

But there’s far more to product insights than UX. It is especially important to obtain detailed product evaluations when speaking with technical buying personas, such as developers, heads of infrastructure or technical leadership (CIOs).

For Clearsighted, getting these product insights starts with watching product demos and internal training videos to get to know clients’ solutions. It then continues with a thorough onboarding, so we know where extra probing into product decisions is needed.

Sales Experience

This is one of the reasons Sales should never own win-loss, and one of the reasons internal champions need to tread a little carefully (because Sales can think win-loss is a witch hunt, even though it’s not!).

In truth, it’s rare that buyers have specific negative things to say about sellers. If they do, it’s usually around sellers being too over-zealous, or promising the moon without being able to back it up. Far more frequently, buyers feed back things about the sales process in general that can be improved, or which were viewed positively.

In the case where a buyer does have something great to say about a particular salesperson, win-loss can help understand specifics and to circulate these so that the rep’s best practice can be replicated among other AEs.

The are the kinds of questions your win-loss interviewer should ask about the sales experience:

• Won: “You said that the rep built a great relationship with you. What were some of the things they did?”
• Lost: “You said that X wasn’t communicated clearly. What would you have liked to see instead that could have made the picture clearer?”
• “How were you sure that [vendor] would be a good partner to you? What did the rep show you or say to you that gave you confidence?”

These kinds of questions often uncover interesting additional detail, such as the account teams that competitors put together in order to close deals.

Customer Success Metrics

I’ll add this right at the end, because it’s one that’s often neglected. Essentially, what will success look like for your customer if they pruchase your solution?

What would it look like internally for that pain to be ironed out? What gains in productivity will be realised? What $$$ savings can they expect? Essentially, what should the ROI be?

Conclusion

If we are to really boil things down, win-loss should uncover insights which are one of two things:

1. Actionable: i.e. ‘I need to change A or replicate B in order to win more deals.’
2. ‘Ingestible.’ I use this word because it describes a process whereby Product Marketing, Sales and Marketing ingest the language your customer uses and make it the foundation for how you talk about your product or solution.

If any of the following categories of information are missing from your win-loss program, it may be time to seek out a new provider or re-evaluate your current approach.