Win/Loss Analysis: A Guide for Product Managers

Are you regularly engaging in a win/loss analysis process?

Building a great product isn’t just about following that dream roadmap you built when you first envisioned it, you know.

You’ve got to be finely attuned to your market’s needs, which can fluctuate as competitors pivot their offerings, new technologies emerge, and best practices change.

One of the best ways to stay locked into your customers’ needs is to align with the sales team and collaborate on win/loss analyses.

The value here comes from the analysis involved, which is exactly what we’re going to dive into here.

We’ll cover the reasons behind conducting win/loss analyses, how to calculate your own, and how to analyze data and determine appropriate actions for improvement.

What is win/loss analysis? 

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A win/loss analysis is a GTM (go-to-market) process for uncovering the reasons behind your success and failures in converting sales prospects to paying customers.

It involves first calculating the ratio of wins to losses (that is, prospects that you turned into customers vs. prospects who didn’t buy from you).

Then, you dig deeper to analyze the reasons behind both wins and losses to identify changes you can make to improve your conversion rates and win/loss ratio going forward.

Why conduct win/loss analyses? 

So, what exactly is the point of conducting a win/loss analysis?

What does it tell you as a business leader?

Understand why customers buy

The “win” part of the win/loss analysis usually gets a little less attention (we tend to gravitate toward problems).

But it's just as important to understand why and when you when as the reasons behind your losses.

Why?

Because it’s often easier to double down on what works than to try and fix what’s broken.

By understanding the factors that influence success in the sales arena, you can improve things like targeting in your prospecting or help low-performing reps learn the word tracks that more successful salespeople use to win customers.

And why some customers go to competitors 

Then, of course, there’s the other side of the win/loss analysis:

Why you lose deals.

This is also incredibly important. You want to know why customers choose a competitor over you in order to:

• Alter your product positioning or roadmap 
• Help sales reps understand when a prospect is likely to be a lost battle from the get-go
• Improve the talking points on your sales battle cards

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Understanding when and why you lose will help you figure out how to win more.

Improve sales collateral and marketing material 

That understanding (about when you win and why you lose) flows down into an ability to make improvements across all GTM and product teams.

This might look like:

• Adjusting positioning and marketing messages
• Helping sales out with better defined personas
• Enforcing process changes to align sales and marketing teams and prevent mixed messages from reaching customers 

This isn’t a one-and-done process. Keep your sales and marketing assets in a place and format where they can be easily and quickly updated.

Make customer-centric adjustments to the product roadmap 

Sometimes, you’re losing deals — not because of what your sales or marketing team is saying (or not saying).

Sometimes, you literally just don’t have the right features to serve customer needs.

When digging into why you’re losing prospects, for example, you might learn that many of your competitors offer a feature or function that you haven’t developed yet.

If that’s the only reason behind a lost deal, then building that feature would result in immediate revenue growth.

Improve customer success to prevent churn 

Learnings from sales and marketing can also filter down to post-purchase processes and policies, such as how customer success team members manage existing clients and combat churn.

For instance, if customer success understands what objections arose during the sales process, they can be used to anticipate future concerns.

Or, customer success managers might want to understand why competitors win deals. With this info, they can be prepared to handle objections that might arise as part of a renewal conversation.

Set a benchmark to improve upon 

Running your first win/loss analysis gives you a metric that you can focus on improving upon.

This can be an important way to align sales and marketing teams toward a common goal (winning more deals and losing fewer).

With that in mind, let’s look at how you calculate the thing.

How to calculate your win/loss ratio 

The win/loss ratio formula is super simple:

# of Opportunities Won / # of Opportunities Lost = Win-Loss Ratio (%) 

Say, for example, you won 10 deals last month and lost 14.

Your calculation would look like this:

10/14 = 71%

You may also want to calculate your win rate alongside your win/loss ratio, the formula for which is:

Win Rate (%) = # of Opportunities Won / # of Total Opportunities

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Which, in the above example, would be 10/24 = 41.6%

This is probably a more practical figure. It's much more intuitive.

A 100% win rate means you won every single deal you pursued for that period. On the other hand, a win-loss ratio of 100% means that you won as many deals as you lost. 

Since we tend to associate 100% with the maximum total score, this ratio is kind of confusing.

How to conduct win/loss analysis

Ready to conduct your first win/loss analysis?

It’s pretty easy. Just follow these four simple steps.

1. Pull your data together 

Start by gathering all relevant information you have available.

Your CRM (customer relationship management) software, as well as sales software (like reporting suites, competitive intelligence, and engagement solutions), are a great place to begin for quantitative insights like:

• Job titles or buyers vs. non-buyers
• Common pain points raised during sales conversations
• Objections that regularly lead to lost deals

You might also collect data from marketing automation solutions (such as common lead sources or how buyers vs. non-buyers typically interact with different content) and dedicated competitive monitoring tools.

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Consider investing time and resources into customer feedback surveys and interviews for deep, qualitative data. 

For example, you might conduct long-form face-to-face interviews with a few of your most important customers (those who closely fit your ideal customer profile), as well as with non-buyers, to learn more about closed/lost sales opportunities.

2. Analyze, filter, and report 

Step two of the win/loss analysis is the actual data analysis part.

Start by calculating your win rate and win/loss ratio. 

Use this to establish a benchmark so you can measure the impact of any strategies you put in place in step three.

This will also be important for establishing benchmarks against which you compare further, with more detailed analyses.

For instance, you might calculate that your win rate is 30%. Later, when breaking down your win rate by customer segment, you find that one segment is performing at 40% while the other is holding you back with a win rate of 20%.

By comparing both to the average, as well as to each other, you can see where opportunities for future focus might lie.

Next, you’ll dive a layer deeper.

Using the notes from your CRM and sales tools, as well as the conversations you conducted with customers (and non-customers) in step one, build a breakdown of:

1. Common reasons people say they bought
2. Common reasons people say they didn't 

Look for trends here. If there is a common cause of won or lost deals, and this information has come directly from customer feedback, you’ve got a perfect opportunity to start improving.

Finally, break down your data in as granular detail as possible, using filters such as:

• Lead source
• Competitor
• Customer segment
• Team or salesperson

Take the “competitor” filter as an example.

You’ll want to look at your lost deals to understand which customers are taking a larger share of your prospective deals. Then, consider subjective qualitative feedback in this context — consider how you might update sales collateral and battle cards to improve your sales reps' ability to handle objections or even overhaul the entire sales strategy.

3. Determine appropriate actions 

Now that you’ve gathered, analyzed, and reported on your data, it's time to move to step three of your win/loss anlaysis: taking action.

The specific actions you take depend on what the data say about your won and lost deals, but here are a few starting points to consider:

• Changes to product — such as developing a new feature or making changes to an existing one when this is the reason why you’re losing deals to competitors
• Changes to internal processes — for example, if you’re losing customers due to an overly complex sales process
• Change to battle cards — to help your sales team handle objections better
• Changes to pricing — like adopting a new pricing model or simply dropping your list price to remain competitive
• Changes to messaging or positioning — for instance, making subtle changes to marketing messages on your landing pages to pre-handle sales objections that regularly pop up and cause deals to go down the drain
• Changes to targeting — e.g., shifting your advertising budget entirely to the audience segment that your sales team has the most success with

In some cases, you might just need to invest in more training for GTM team members. 

For example, when breaking down wins vs. losses at the salesperson level, you might find that a couple of reps are underperforming compared to others.

Organizing additional training and development opportunities (such as a buddy system with one of the more experienced reps or using a tool like Gong to pull out conversational intelligence insights) could be the solution here.

4. Return to step 1 

All finished, right?

Not quite.

The win/loss analysis is not a one-and-done process. Rather, it's something you should be reviewing and analyzing on a regular basis (monthly or quarterly, depending on your age, stage, and growth goals).

Ongoing improvement is the name of the game here!

How Ignition helps with win/loss analysis 

Ignition connects with your CRM (HubSpot, Salesforce) and automatically pulls over deal data. 

Then, our AI engine reads that data and figures out what deals had competitors involved, as well as the notes your salespeople leave on the deal record.

With this, we can provide valuable insights into why you’re losing deals and to whom.

We can also help you understand when and why you win deals. These actionable insights can be surfaced to sales battle cards, helping every rep position your solution in the way that helps them win the most. 

Want to learn more? Head here for automatic and affordable competitive intel.