How to Measure Sales Enablement Success and Strategy

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As more companies are implementing sales enablement strategies to align their sales and marketing strategies to the buyer’s journey, today’s trend will become tomorrow’s necessity.

The rise of data-driven enablement teams is especially noticeable today, which makes measuring your company’s sales performance easier but more rigorous. And with data comes important metrics and measurements.

First, keep these stats about sales enablement in mind:

  • 75% of companies using enablement tools increased their sales.
  • Companies with these strategies are 52% more likely to be in close alignment with the buyer’s journey.
  • 74% of high-performance companies have strong sales and marketing alignment.
  • 59% of companies with sales enablement functions surpass revenue targets, and
  • 72% surpassed them by 25%.

As you can see from the numbers, a working sales enablement strategy is important to sales and marketing effectiveness. 

But how did these numbers come about? In short, the question to keep in mind is, how should you measure sales enablement success?

Before you measure sales enablement strategies

It’s extremely important that you prepare your strategy, in detail, before you begin measuring anything. This includes making sure you have an initial strategy ready with a proper sales enablement team structure.

Throughout the entire process, ask yourself if these sales enablement efforts will enhance your company’s sales process. Also, will it be right for team structure?

After establishing the basics and finding the correct way of implementing this strategy, you need to determine which sales enablement activities align with your existing sales and marketing goals. Are you looking to attract new customers? Convert more leads? Or trying to improve your company’s attention to sales strategies?

These questions are all about determining what the best sales enablement platforms and tools are for you. 

For instance, the cloud-based service DYL is perfect for your all-in-one communications needs that also automates workflows to reach out to new prospects and leads.

Therefore, you should know whether you need a communication-based tool, CRM platform, or a more powerful AI-powered sales intelligence service. All of which perform distinct functions depending on your sales enablement goals and metrics.

Team meeting between sales professionals

Guide to Measure Sales Enablement Success

By measuring the success of your sales enablement efforts, you are asking yourself the basic questions: How do I know the strategy is working? Where should I look, the sales reps, the number of leads to customers?

Below you will find a list of metrics and tools that will help you keep track of the effectiveness of a sales enablement program and show a guide on how to improve sales performance.

Lead to customer conversion rate

The conversion rate of leads to customers is one of the most important metrics to determine your company’s sales efficiency. One of the many KPIs your company should already be measuring, the sales cycle length is also a crucial sales efficiency benchmark for enablement success.

The lead to conversion rate will tell you, broadly, how effective your sales reps are succeeding given the amount of support from enablement strategies they received. If after implementing the new strategy and tools you see no increase, that will tell you more than other measurements whether the sales enablement strategy is working.

ROI of sales enablement campaigns and processes 

Measuring the return on investment rate will give you a more data-driven approach to the success of how the sales enablement strategy is affecting the bottom line.

For this, measurements including average selling price as well as average discount price over the average sales length will tell you about the ROI over time. Many different processes contribute to this number, including how well the sales reps training is and what platform they’re using connected to the buyer’s journey. 

In general, this metric and the lead to conversion rate work well in providing a good overall picture of measuring sales enablement strategies.

Sales training

Since sales enablement is all about supporting the sales rep’s function of selling your company’s services and tools, training them is key.

That means teaching them the ins and outs of products and the best means of selling them. You can sit with them physically and build a more personal connection, and conduct surveys to understand their opinions and suggestions.

It’s important to ensure a smooth yet swift onboarding time to push for their all-important time to first deal. The sales reps are the backbone of most companies, so be sure to measure their performance at every step. This will provide you with valuable insight into the reality of your sales enablement success.

Content performance

Whether your company uses case studies and white papers, or social media posts and paid ads, the performance of content is another important metric to pay attention to.

Having the marketing team create a piece of content isn’t enough. These pieces need organization from a sales enablement content management platform that enhances the sales reps’ ability to utilize content quickly and effectively. Most companies use CRM software, which usually comes with many automated tools and metrics, for this purpose.

Remember that the marketing team plays a crucial role in the success of the sales team!

Win rate

A specific measurement that many sales managers look for is the win rate, or the percentage of qualified leads that sales reps won. The win loss rate is a simple binary at determining the level of opportunities wasted.

A sub-metric to this is the competitive win rate, which measures your win rate against competitors. More likely than not, your direct competitors will be using sales enablement strategies for similar aims. Therefore, keeping track of that should be an important focus.

The quality of the opportunity gained is another thing to keep in mind, otherwise you might be open to a higher churn rate than usual.

Attribution reports

After you’ve seen the sales enablement strategy from the sales and marketing teams’ perspectives, you need to turn around and check in on the customer.

A metric you can focus on for this are attribution reports, which tracks what content the prospects and leads are interacting with at certain points in the buyer’s journey. You’re seeing why and when you gained a customer. This measurement will take the form of calls to action including clickthrough rates and click to submissions.

A related customer metric is the net promoter score, which surveys whether the customer will return or not. Putting yourself in your customer’s shoes is often an overlooked strategy in the overall sales enablement strategy. Therefore, by doing so, you can increase your competitive edge.

Quota attainment

Lastly, sales quota attainment measures a sales rep performance over time, hopefully showing the positive effects of their continual training. Just like the lead to conversion rate, a sales rep’s quota attainment measures the overall success of the sales enablement strategy implementation.

More than any other metric, a decline will tell you if the sales team is struggling with the new tools put into place, and that you should reconsider if it persists. If anything, you can also use a sales target or the average length of your sales to measure performance.

If you follow these guideposts in measuring the success of your sales enablement, then you will have a great understanding of the overall picture. But that doesn’t mean difficult problems won’t arise, even for the perfect strategy implementation.

Team of sales staff celebrating a big win

The Main Challenges to Measure Sales Enablement

The main point for measuring anything in life is to define. By defining something, especially regarding company stakes, you turn it into useful information that can reduce uncertainty.

But the problem is that uncertainty is a constant. Therefore, measuring the success of your sales enablement strategy needs to also be a constant.

As discussed before, continual sales training is one of the most important methods for reducing the uncertainty of your company’s aim over time.

Here is a small checklist of future uncertainties worth addressing or thinking about early on:

  • How will your company’s goods and services fit the future landscape of digital automation, AI-powered tech, and data-drive approaches to sales enablement?
  • How will your potential and existing customer base change over time and what services will they need?
  • What measurements in the future will be more important to your success in the future that isn’t a focus right now?
  • When you hire sales reps and have others leave, will your strategy need adjustment for the new hires needs or remain consistent to the original plan?

These and many other challenges will happen in the future, so be sure to get ahead to reduce uncertainty.


It would be easier to remember the measurement of sales enablement success as a three-party strategy over time: preparation, implementation, and outlook. 

Prepare your strategy with the metrics that will be important to you. Implement your strategy with a set of measurements readily available and the ability to remain flexible. Look towards the future and remember that tomorrow’s standard is today’s forward-looking strategy.

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Chris Rhine
Chris Rhine


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