10 Proven Strategies to Boost Your Sales Win Rate

You’re on track to miss your sales quota.

You have a healthy pipeline, but your win rate has dipped. At the current rate, the team is off target to hit this year’s quota. The executive team is looking to you for answers. What can you do?

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I’ve been there. Based on my growth-stage SaaS experience, I’ve compiled a checklist of 10 factors that consistently drive win rate. This list is ranked from most to least likely to affect closings with the goal of articulating how to understand, diagnose, and solve sales problems so you can start winning more.

Win Rate Diagnostic Checklist

There are 10 variables I’ve found most likely to be win percentage drivers:

1. Targeting
2. Qualification
3. Value Proposition Clarity
4. Speed to Lead
5. Relationship Building
6. Product Market Fit
7. Differentiation
8. Touchpoints
9. Pricing
10. Culture

Let’s dive in. 

1. Targeting

The Impact of Targeting 

The best sales process in the world won’t matter if the leads going into it aren’t a good fit for the product. Precise targeting focuses your team’s energy on buyers who are the best fit for your solution. By ruthlessly pursuing your ideal customer, you can transform your team’s efforts from random acts of sales to strategic, high-conversion interactions.

How to Diagnose a Targeting Problem 

There are a few ways to diagnose a targeting issue:

1. Analyze your win/loss data. Identifying patterns in successful and unsuccessful deals will help you better define ideal target customers.
2. Analyze customer data. Finding common traits among your best customers (such as industry, company size, or specific pain points) gives you a clearer view of your Ideal Customer Profile (ICP).
3. Survey your current customers. This will help you understand why they chose your solution. Then you can compare their responses to your ideal customer profile.
4. Review your team's feedback on lead quality. Identifying common objections can help you pinpoint misalignments in your targeting strategy.

Any or all of these methods should help you pinpoint whether your targeting strategy needs an overhaul.

Case Study: How Lattice Doubled Win Rate with Better Targeting

Lattice had a problem: their closed-won ratio wasn’t lining up with their sales team’s activity (5-6 calls per day). After diagnosing the issue, they took these three steps to improve their targeting:

1. They defined their ICP. Lattice found out what kinds of organizations got value from their product and identified characteristics these organizations shared in common.
2. They decided not to pursue any deals under $4k. Customers spending less than that amount weren’t getting the full value from the product, so they were likely to churn anyway. 
3. They paused their product-led growth (PLG) motion. Buyers could still experience the product on the website, but the sales team started closing all deals.

After implementing these tactics, Lattice’s win rate doubled, going from 20% to 40%. 

2. Qualification 

The Impact of Qualification

Too many sales teams qualify early and easily, pursuing a “yes” from buyers. Getting a “no” quickly instead helps your team spend less time with bad fits and more time on real opportunities. Focusing efforts with better qualification will help the team win more of the deals in the pipeline.

How to Diagnose a Qualification Problem

Follow these 4 steps to see if your qualification process needs work:

1. Analyze conversion rates. If conversion is high in the qualification phase, but drops in later stages, there’s probably a qualification problem.
2. Evaluate team feedback. Asking your reps about the challenges they’re facing during qualification uncovers gaps in the process.
3. Review qualification questions. If the questions don’t align with your Ideal Customer Profile (ICP) or effectively identify key decision-making factors, you probably have a qualification problem.
4. Examine the sales cycle. Compare the average length of each stage. If contacts are spending a lot of time in the qualification phase, there’s probably a problem there.

Once you’ve found an issue with qualification, you can get to work on solving it.

Case Study: How Coschedule Grew Revenue by 59% with Better Qualification

Coschedule bootstrapped their way into growth. Here are the steps they took to improve their lead qualification:

1. They used a simple framework. Coschedule used the BANT framework (Budget, Authority, Need, Timeline) to qualify deals. This helped them focus their efforts on the deals most likely to close.
2. They discussed deal quality as a team. The Coschedule team met to talk about what made some deals a better fit, and others less so. Sharing intel regularly helped everyone understand what a quality deal looked like.
3. They asked more questions. This helped the Coschedule team better understand the goals and motivations of buyers, and how their product solved their problems.
   

“The more you can learn about an account, their current challenges and their goals, the easier it becomes to identify and then execute on a large growth opportunity,” said Kris Nelson, former head of Revenue at Coschedule.

Better qualifying was a driving factor that led Coschedule to $10.3M in revenue (a 59% YOY increase) and 8,000 customers in 2024.

3. Value Proposition Clarity

The Impact of Value Proposition Clarity

If buyers don’t see how your product solves their problem or why it’s better than alternatives, they’ll hesitate to move forward. A clear value proposition communicates the unique benefits your product offers—and helps differentiate it from competitors. When buyers better understand how your product addresses their pain points, they’re more likely to move forward.

How to Diagnose a Value Proposition Clarity Problem

You can do a few things to pinpoint a problem with your value proposition:

1. Test value proposition messaging with buyers. Ask them, “Is the value of the product clear?” If it isn’t, they’ll tell you.
2. Compare your value proposition with customer pain points. If there is any misalignment, you’ve got a problem. This method only works if you have a clear understanding of pain points, so hopefully you’ve done some research on this already. 
3. Evaluate substitutes. Look at what else buyers are using or could use to solve the pain points you’ve identified. If your value proposition isn’t clear about how your product is better, that’s a problem. 

After you identify a value proposition problem, there are a few things you can do to solve it. 

Case Study: How eVisit Grew Revenue to $12M with Value Proposition Clarity 
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At eVisit, the revenue team took several steps to make sure the value prop was clear to buyers:

1. They highlighted measurable outcomes. When they could point to a metric the product helped improve, like time savings or cost reductions, buyers understood the value better. 
2. They tailored messaging to specific customer pain points. When they hit on the problems buyers experienced and highlighted how the product solved them, buyers saw the value clearly. 
3. They equipped sales reps with case studies. Social proof and return on investment information helped buyers see themselves using and benefiting from the product.

By taking these steps, among others, eVisit quintupled growth to more than $12M in annual revenue in less than a year.

4. Speed to Lead

The Impact of Speed to Lead

Waiting too long to contact a buyer will cause them to lose interest. The sooner you reach out, the more likely they are to still acutely feel the pain your product can solve. Following up on information requests as soon as possible will drastically increase the number of deals you win.

How to Diagnose a Speed to Lead Problem

To uncover a problem with speed to lead, you can do several things:

1. Analyze your current speed to lead metrics. If your response times are longer than you’d expect, you have a speed to lead problem.
2. Evaluate your sales team's capacity. Looking at the average number of leads your reps work tells you whether some of them get too many leads assigned to them.
3. Identify bottlenecks in your lead routing process. The bottlenecks could be untouched leads sitting in the queue, leads missing necessary information, or leads routed to the wrong salesperson.

If you find an issue, you can take action to unlock more growth.

Case Study: How eVisit Increased Win Rate with Faster Lead Response

At eVisit, we uncovered a problem with our sales team’s lead response times. We took three steps to solve the problem:

1. We analyzed the data. We learned that leads contacted within five minutes of submitting their information are more likely to buy. 
2. We started a friendly competition. We challenged our reps: who could get the most leads on the phone while they're still on the website? 
3. We tracked the results. Deals contacted while the buyer was still on the website were five times more likely to close. 

After we implemented this change, we saw our win rate go up by roughly 15%. 

5. Relationship Building 

The Impact of Relationship Building 

Even for SaaS models with shorter sales cycles, relationships with buyers matter. If you don’t build trusting relationships, buyers won’t see the value, and they won’t care. They’ll ghost you. Forming real relationships with buyers will get them to care about your product and want to buy it from you.

How to Diagnose a Relationship Building Problem

Take these steps to see if you have a relationship building problem:

1. Analyze communications with buyers. Evaluate the quality and personalization of the communications between your team and buyers. Shallow or generic messaging can hinder relationship building at any stage.
2. Review buyer feedback. Examine any available feedback from buyers about their interactions with your sales team. This will help you identify any recurring complaints or concerns. 
3. Assess communication skills. Evaluate your team's ability to actively listen, ask insightful questions, and tailor their messaging to each buyer’s needs.

If any of these activities uncovered an issue, read on for the actions you can take to address it.

Case Study: How Gong Built Relationships and Grew to $332M in Revenue

Gong used relationship building tactics to improve their win rates. Here’s what Chris Orlob, a former revenue leader at Gong did:

1. Understand buyer pain points. Showing buyers that you get what they’re going through builds trust and rapport.
2. Ask targeted questions. This keeps conversations focused on priority problems that your product can help them solve.
3. Uncover the “need behind the need.” Getting to deeper problems sooner gives you more time to explore solutions and build a solid relationship with  buyers.

Gong’s approach is working. They reached $332M in revenue and 4,000 customers in 2024.

6. Product Market Fit 

The Impact of Product Market Fit

Sometimes you reach the right buyers, but your product is misaligned in a few key areas. When your product doesn’t fully meet the needs of buyers, you’ll likely see your win rate dip. Addressing product market fit can get you back on a growth trajectory.

How to Diagnose a Product Market Fit Problem

Take these steps to assess whether product fit needs improvement:

1. Run the 40% rule test. This means asking users how they would feel if they could no longer use your product. If fewer than 40% of users say they would be "very disappointed," you probably have a product fit issue.
2. Monitor user engagement. Low usage growth and customer retention indicate potential problems with product fit.
3. Gather qualitative feedback. Interview customers to understand pain points and unmet needs. Recurring themes can point you to issues with product fit.

When you’ve zeroed in on the problem, it’s time to take action to solve it.

Case Study: How Populate Used Product Fit to Up their Win Percentage

Populate took these steps to effectively address product market fit:

1. They kept in constant contact with potential users. This helped them better understand buyer needs to inform the product.
2. They continuously iterated on the product. This allowed them to try multiple product designs and get feedback from user testing. 
3. They tailored the product to customer needs. Making customer-centric design choices made the product a better fit for target buyers.

Populate’s efforts to improve product market fit paid off. They saw meaningful increases in user engagement and satisfaction, which helped them sell their product.

7. Differentiation

The Impact of Differentiation

Differentiating your product helps you stand out in a competitive market. Better differentiation will help you sell more effectively and close more deals. If buyers can’t tell you apart from your competitors, you lose a critical competitive edge.

How to Diagnose a Differentiation Problem

Take a look at these factors to see if you have a differentiation problem:

1. Analyze pricing. If you find yourself constantly lowering prices to win deals, it's a sign that you're struggling to differentiate your offering.
2. Examine deals lost to competitors. When buyers consistently choose other options, it may indicate that your unique value proposition isn't clear or compelling enough, especially if there are usual suspects.
3. Gather customer feedback. If they struggle to say why your solution is better than  others, you have a differentiation problem.

When you have a good idea that your differentiation needs some work, you can get started on fixing it.

Case Study: How 700 B2B Companies Differentiate their Way to More Wins
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In an analysis of more than 700 B2B sales, several differentiation tactics proved most effective:

1. Differentiate on qualities that matter to buyers. Even ideal buyers have various goals and desires. Successful sales reps focus on demonstrating superior value in the areas that matter most to their buyers.
2. Create scarcity. Buyers are more likely to move forward when they believe that what you have has rare value. 
3. Make promises that align with delivery. If your product delivers on every promise, or even more, buyers are much more likely to be satisfied with it.

These tactics were the top drivers of successful differentiation.

8. Touchpoints 

The Impact of Touchpoints 

Spending the right amount of time with buyers can make a huge difference to a deal. 80% of sales require at least five follow-up calls. More touchpoints and time with buyers increases win percentages. 

How to Diagnose a Touchpoint Problem

You can dive into multiple areas to diagnose a problem with the number of buyer touchpoints:

1. Look at the number of calls made with each buyer. If you have longer sales cycles and fewer than five calls per buyer, you might have a touchpoint issue.
2. Compare calls made to closed/won and closed/lost metrics. If there’s a correlation between fewer calls and fewer deals, you probably have a touchpoint problem.
3. Analyze your sales process. If you haven’t outlined an appropriate number of calls for your team to make, they probably won’t have enough touchpoints with buyers.

Case Study: How Tallwave Ramped Up Win Percentage with More Touchpoints 

When I was leading Marketing and Strategy at Tallwave, we diagnosed a problem with the number of touchpoints in our deals. Here’s what we did:

1. We analyzed win/loss data. We found that if a buyer got to a seventh meeting, they were 80 percent more likely to close. 
2. We redefined our sales meetings. We created a process where each meeting built on the last. 
3. We gave buyers cliffhangers. Just like the end of a great TV episode, we left buyers wanting more so they would crave another meeting.

After consistently implementing these changes, we saw our win percentage go up by about 30%. 

9. Pricing

The Impact of Pricing

The relationship between pricing and win rate is complicated, and it varies by organization. Lower prices generally increase win rates, while higher prices tend to decrease them. Strategic price increases can sometimes lead to higher revenue even with a slightly lower win rate. Discounting can affect win rates as well. Adjusting your pricing to match your strategy will improve your win rate.

How to Diagnose a Pricing Problem

To find out if your pricing strategy is off, take this approach:

1. Assess the frequency of discounting and promotions. If your team is giving frequent discounts, you probably have a pricing problem.
2. Analyze deal cycles and approval times. If a lot of buyers stall in negotiations, pricing could emerge as a recurring theme.
3. Monitor churn rates. Pricing may cause too many customers to churn. 

Found an issue? You’ll want to take the next steps to solve it.

Case Study: How eVisit 10xed Revenue Per Customer with Better Pricing 

In the early days of eVisit, we started seeing churn go up and win rate go down. We analyzed pricing data, and learned that pricing was a major factor in these changes.

1. We moved upmarket. Our analysis showed that larger enterprise customers were less likely to churn, so targeting these buyers set us up for a pricing adjustment.
2. We increased pricing. This move conveyed the value of our solution to the upmarket customers, and allowed us to increase average revenue per customer.
3. We added an implementation fee. This change reflected the high-touch nature of implementation for an enterprise customer.
4. We lengthened contract periods. This secured revenue for more time and encouraged longer term investments from customers.

After implementing these changes over the course of two years, we saw churn go down by 75%, the win rate go up by 15%, and average revenue per customer increase by over 1100%. This pricing strategy empowered us to focus on a more valuable ideal customer. 

10. Culture 

The Impact of Culture

Culture can undermine every other element on this list. The values and behaviors you encourage and discourage with your team greatly affect their motivation and performance—which of course impacts your win rate too.

How to Diagnose a Culture Problem

How do you find out if your team has a culture problem? Here are three diagnostic activities you can use:

1. Assess alignment between desired and actual and sales practices. Are you doing what you say you’re doing? If not, there could be a cultural disconnect.
2. Analyze turnover rates. Frequent departures, especially of top performers, can indicate underlying cultural issues.
3. Evaluate team collaboration. A toxic sales culture often prizes individual excellence over effective teamwork.

When you’ve discovered a culture problem, you can make moves to address it.

Case Study: How 3 Leading SaaS Sales Orgs Create Winning Cultures 

Culture is difficult to influence, especially once it has had time to grow on its own. However, it’s still critical to winning more deals. Here’s what some of the top performing SaaS sales organizations have done to build healthy cultures:

1. They invested in learning, development, and coaching. Hubspot set their sales team up for success with ongoing training and education. This communicated the company’s investment in their team.
2. They encouraged trust and transparency. Salesforce consistently communicated the importance of these cultural values at every level of the organization. This improved teamwork and autonomy. 
3. They promoted consistent performance tracking. Lyft implemented consistent real-time KPI reporting, which improved sales performance.

There are many ways to improve the culture of your team. Choose the approach that best suits your unique context.

Continuous Win Rate Improvement

The truth is, any or all of these factors could be affecting your win rate now. There’s always something you can do to win more of the opportunities in the pipeline. Improvement is a never ending battle. Use this diagnostic tool to continuously uncover and solve problems in your sales process. 

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To learn more about how Chief can help you with win rate problems, don’t hesitate to reach out directly.

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