APPROACHES TO WIN-LOSS & CHURN ANALYSIS
Petr Zelenka
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We spend millions on sales, marketing, and CS without truly knowing why we win and lose deals and accounts.
You cannot win more unless you fully understand the truth about why you win and lose.
Win-loss analysis helps you fix gaps in your sales, CS, marketing, & product by uncovering the right answers to questions like:
Rigorous Win-loss analysis can improve win rates by up to 50% and revenue by 15-30%. (Gartner)
That's why I met with many elite revenue leaders to discuss their strategies and asked:
What's your approach to win-loss analysis?
Enjoy their quotes:
When I got here, I said we needed to know why we lost deals. We managed to schedule 30-minute interviews with 80 evaluators from lost deals. The lessons we learned from them completely shifted our company. We shifted our messaging, website, steps in our processes, demo scripting, everything.
My North Star is improving the win rate. There are many aspects that influence it. Do we have the right pitch that resonates with the market? Did we pick the right pricing points and pricing methodology? How do we derisk the buying process?
We have an entire team of professional researchers who will conduct new business win-loss and churn interviews. We are able to get really good insights about why we win and lose deals or why customers leave us. It's interesting to see what sales think, what CS thinks, and what the buyer actually says. Our researchers create deep analysis and give us a lot of details. Our speed of reaction to customers' needs is huge.
The impact was that we made a big pivot that helped us to solve bigger high-priority problems for our customers, and we also changed our target persona. Better positioning helped us with better conversions. I'd absolutely pay for this service to an external company if I were somewhere else.
Regarding win-loss analysis, we have weekly calls. We get very detailed about the competitive aspects, our pricing, product, etc., and then we roll that up to regions. The win-loss reasons can be very different regionally dependent because different regions care about different things. When we know what to add to our product roadmap, we go back to prospects to win them back. Typically, we lose on price but win on accuracy, speed, and integrations.
We also have predictive data models for churn analysis, renewals, and the performance of every rep. We can also use AI to predict issues throughout our customer base that would affect our renewals.
Some buyers called me, offering their feedback on why they chose somebody else. It's rare, but they call me to say that they have something we should know. It's painful to listen to the buyer telling you why you lost, but it's very valuable. Most of the time people are actually not willing to give you honest reason why they did not chose you.
I used to hire somebody to do that for us and I'm also very curious so I've always gone back and ask. Half the people actually tell you something. The other half feels under pressure and do not want to talk to you at all. Everybody needs win-loss analysis services. The hiring and staffing industry is very competitive, and deals are large.
Going after closed-lost opportunities is our fastest pipeline generator. We run bi-monthly closed-lost campaigns to win opportunities back. If a customer becomes unresponsive, AE might send a couple of emails, but when we try different strategies, we often figure out it's not lost. It is also our favorite campaign to run because we need to read the context of the opportunity and learn more about what we do and the pains of our customers.
We do win analysis of your big net new logos and document as much as possible. We understand why we are winning, but I'd be helpful to understand more why we are losing. We do not do enough loss analysis.
Most companies have a standard picklist in Salesforce, such as "unresponsive," "cost," etc. I believe there is only one reason you lose deals. You didn't give the customer what they needed. That's it. They did not believe you could get them what they wanted. "Unresponsive" is the easy pick for salespeople. There should be: "I did not articulate the value and ROI for the customer" in picklists.
If I buy a car, I want to protect my family. I'm not really buying a car. You win the deal if you understand and articulate that value for me. I do not know whether I need to even buy your thing so do not ask me about my timeline and budget. Most sales training trains people to ask questions for the company, not for the customers. That's crazy.
Everybody loved talking about their wins, but losses were more helpful. We should celebrate our losses and learn from them. If you can achieve that in the first year as a CRO, it's absolutely fantastic. There is a rule that your loss reports should have at least 3 paragraphs. It makes you think and get deeper. Also, have a win-loss field in your CRM for AEs and another one for SEs.
I believe every executive should send an email to their counterpart in a lost account and ask why they lost the deal. Executive buyers are often more honest with executives.
Our approach to win/loss analysis blends both quantitative and qualitative data. We gather insights by prompting reps to share details when deals are marked won or lost, analyzing the journey, reviewing calls, and surveying clients. Third-party interviews are incredibly useful for adding depth, but we find they’re most worth the investment when applied at scale.
But we don’t stop at collecting data. When we spot objections, we immediately rally our marketing, sales, and customer success teams to eliminate them before they derail future deals. And when we uncover why someone chose us, we rally around that too — doubling down on what works to drive more wins and create a frictionless sales journey.
"Win-loss analysis is crucial for understanding what drives our success—and where we fall short. By dissecting each outcome, we gain insights into why we win or lose deals and can quickly adjust our strategies.
To get an even deeper perspective, we partner with a third-party firm that’s exceptional at uncovering the full story. They go beyond standard questions, developing their own hypotheses to reveal insights customers might not share directly with us. This isn’t a checkbox exercise; it’s an essential tool. Each month, our leadership team reviews these insights, making swift, data-driven decisions to sharpen our competitive edge."
There always should be a win-loss analysis, and marketing should be part of it to understand why we win and lose deals. The win-loss analysis is critical for your go-to-market strategy and execution.
If you embed win-loss analysis in your go-to-market, then the value is in discussing the insights with other GTM departments and deciding on the best course of action. Everybody can understand their customers way faster this way and save a lot of time because of that. It's feeding the entire organization with great information and eliminates information silos between departments. The question is: who is doing that process? Or how can organizations optmize this process for better results?
What I've seen as very successful is hiring an external firm that understands our solutions and has a great process of conducting interviews with our buyers. They did a great job of capturing the data and gave us a good objective view of what's working and what's not working.
Do we really differentiate? Do we actually know our competitors? How Are we aligned with the top priorities of the account and buyer's needs? If you understand the competitive landscape better, you can stack the odds in your favor and address high-priority needs. We do not lose to indecision. We lose to the client's other higher priorities they focused on.
CRM win-loss reasons only give a partial view. If “bad timing” is the main reason for lost deals in your CRM, what does that really tell you? It’s vague and not actionable. Often, people make assumptions about why they’re losing deals without actually verifying. “Bad timing” can’t be the only reason.
Reps and leaders need to go directly to the market and ask. What are prospects actually saying about why deals fall through? Sales leaders should make the effort to call lost accounts and ask for honest feedback. Getting real insights from prospects on why they’re not buying sets you up for greater success.
I love making these win-loss calls by myself. In these conversations, I ask our buyers why we lost and what we could have done differently. Getting lost customers on the line is critical, but also very hard to get their time and attention.
I'm busy as a sales leader, so I manage to talk to 10 people a year and do it as much as possible. I found that high executives, such as CFOs, are more straightforward and more open to sharing honest feedback than some mid-level managers.
We analyze our wins and losses twice a month to see how the experience can help us win more engagements. There is no shaming. At first, people were uncomfortable. They were unafraid to share because we built a culture where there was psychological safety. Our people are able to admit and have the courage to speak about their mistakes.
Our wins always come down to our people. They are very agile and have a growth mindset. Our losses usually come down to the fact that we did not ask the right questions.
We have a series of questions once we win and lose a deal in our CRM. Then, we compare our CRM data with Gong's data and trackers. We uncovered that reps are not building good enough business cases, and we don't get funding without tying it to the top 3 priorities of the business.
I've used external vendors running win-loss interviews with buyers. If you are willing to pick up the phone, you can do it internally, but there is always a strong internal bias that influences the results. These external providers should help us translate win-loss insights into better processes. They might interview our executives and advise whether our strategy in product roadmap, sales, etc., is still valid.
Win-loss is about getting into a deal-by-deal story rather than analyzing large amounts of data. We see deal closure is harder and harder to predict because there has been a lot of uncertain in decision making lately. It's harder and harder to extract meaningful information and insights from buyers about decision-making processes and why they went with a competitor.
In our CRM, every deal needs to have a win/loss reason attached to it. We ask for evidence in a questionnaire. You say we lost to this competitor - how do you know? Who did tell you that? Or are you guessing? It's sometimes frustrating to draw some conclusions out of that. We do not spend enough time internally discussing win-loss analysis.
We have regular win-loss conversations on the leadership level. It's critical to get relevant win-loss information into our Salesforce. We use external agencies to run buyer interviews on our behalf because customers share more detailed information with them. It helps us prioritize our product roadmap and tell us what's really important for customers so we stop losing winnable deals.
When AEs run the interviews, they are already focused on another opportunity they can close. They do not spend a lot of time running deep win-loss interviews, of course. They want to know why they are winning and losing, but they feel they cannot spend their time on that, so it can result in competitive that is not helpful in that case.
The market will realize that CS needs not only tech training but also sales training. Organizations have budgets for sellers, but CS training does not get enough attention. You need customized training for CS to get better at sales skills, not sending to the same training with salespeople.
If CS ensures that the customer sees the impact of our solutions, we know we will grow.
You can learn so many things about your deals when you listen to call recordings.
We do not want to sell bad deals so we are able to predict the likelihood of them churning before we sell to them.
That's why we built predictive algorithms for lead scoring, and we revise it every 4 months. We look at Google's data, the nature of their business, location, ICP, or if the leads have competitors in the 50-mile radius as we help them with online reviews. There are 12 different parameters we include in our churn analysis to make it as accurate as possible.
We have a post-mortem process for every churn with a detailed analysis and plans for what we are changing as a result. We built a customer health monitor score of the user's activity to prevent churn. There are 6-8 parameters to score their health so our customer success team can act on it. We also have a cross-functional churn forecast team that meets monthly to discuss churn and follow up on previous action items.
We use The Command of The Message framework to evaluate where the issue is before our offboarding process and to try to uncover a new business issue to continue the customer relationship. Then, we ran a final interview to capture what we learned, and it turned out to be a very effective customer discovery call. This post-mortem interview always gets very candid.
Our win rate is 70%, and churn rate is only 5% as a tech consulting company. We take all our losses per quarter, and we analyze why we have lost. Where did we go wrong? Did we manage the expectations correctly? Did we build the right relationships in the account? Customers are not clear sometimes on what they want so we lose because of it too. Customers were also waiting and keeping their spending tight before the U.S. elections. Generally, the time to impact for our customers needs to happen in quarters, not in years.
To win more, we need more meeting with qualified leads and our salespeople need to get stakeholders accept the change that is coming with our automation projects.
We hold monthly closed lost reviews with our sales leadership team to provide additional insights into closed lost drivers. Regular closed lost reports are also generated from Salesforce, providing qualitative insights from our sellers. We have also partnered with a third-party vendor to conduct win-loss interviews that provide us with even more qualitative insights. One lesson learned is that buying has become more complex than ever before.
While we have a good understanding of where and why we lose, we need to do a better job of analyzing our wins. There is so much valuable data available, from sequence/messaging results to AI summaries/call recordings, and we need to leverage these resources to do more win analysis.
In win-loss analysis, everyone wants tons of detail from reps. But if we ask for too much, reps might start rushing or filling things in just to get on with the deal. Our focus should be on making the most important questions easy to answer and harder to skip over. This way, we capture the real reasons customers buy from us, which aligns with our win-loss insights.
We win because we understand our customers’ needs well. When we lose, it’s often because the customer’s team isn’t ready for new software, or a competitor makes big promises that rarely last. Our main loss reason is when a client goes silent, and we also run ‘lost interviews’ with clients who leave to learn more.
Now, you might be asking:
Why do so many GTM leaders outsource win-loss or churn analysis?
Imagine your partner broke up with you.
She would never tell you the whole truth about why she broke up with you. She tells you nothing valuable because she doesn't want to hurt you. But she can tell the truth to a friend of yours who can then tell you.
Win-loss interviews are the same.
✅ Buyers don't want to hurt your feelings and are too nice to tell you the truth.
✅ Reps make excuses (product, pricing, etc.) or please buyers to be nice.
✅ Your employees are biased, play politics, and provide vague reasons.
✅ Buyers are afraid you'll try to win them back and hide insights.
✅ Buyers won't admit the wrong choice to you or just say “no,” so it's awkward.
Shameless plug: DM me if you want to discuss how a 3rd-party can get you the truth about your wins and losses so you increase your win rate and mitigate churn.
The top reasons you lose deals are hidden missteps in the way you sell.
That means it's within your sphere of control. You can prevent that, including the 40-60% of deals lost to customer indecision.
We can do better. Let's go.
🚀 Author of GTM Club Newsletter: Accelerating Sales-Led Growth | Sales Director at LINK Mobility
2moGood stuff! I'm gonna steal asking evidence from Aditya Malik starting today!
Chief Revenue Officer at Botkeeper
2moWin-loss analysis is such an underutilized tool, and the truth buyers share with a third party can be a real game-changer. Always fascinating to see how others tackle this challenge!
Marketing Executive - Advisor | Marketing Management, Marketing Strategy | Mentor
2moGreat read Petr Zelenka and enjoyed learning about everyone's different approaches and philosophies.
Director of Sales- General Contractors at OpenSpace
2moThanks Petr Zelenka for letting me be a part of this!! Great job on this and I look forward to staying in touch! 👏 🙌
Senior GTM Tech Leader | Board Advisor | Former Founder & Serial Scaler | Wellbeing Champion
2moReally interesting to read the varied approaches, I was particularly intrigued by the closed-lost campaign. Great work Petr Zelenka, I know how much work you put into this article and your endless research.