How to Measure the Effectiveness of Your Sales Enablement Strategy

How to Measure the Effectiveness of Your Sales Enablement Strategy

Our sales enablement series continues with the final installment of this edition. Previously, we looked at what sales enablement is, how to increase the adoption rate of your sales enablement programs, and the most common mistakes that occur in enablement’s execution. Today we’ll examine how to measure the effectiveness of sales enablement strategy.

Unlike previous posts in this series, we won’t be breaking it down by enablement sector. Why? Because the means and metrics we’ll be talking about don’t correlate one-to-one with measurement to sector. Rather, each type of measurement involves multiple factors that all contribute to the result that a given metric or activity is measuring.

Instead, we’ll be examining ways of enablement effectiveness measurement in two categories: Data-Driven and Intangible Methods.


  1. Time spent selling

    The ultimate end goal of nearly all sales enablement technology is to allow sales reps to complete non-sales activities faster and easier. Therefore, an excellent barometer to use when determining how effective your technology is working is to study the percentage of time spent selling as the weeks and months go by.

    You should already have a baseline in place before you implement the solution, but if not, a rough estimate is between 30-37% of your average sales rep’s time is spent on selling related activities (number varies according to the study). Keep in mind: You might well experience an initial small dip in this metric post-implementation. Do not panic: this is your sales team getting used to the technology and integrating it into their workflow. After a few weeks of reinforcement activities and allowing time for adoption and usage to be second nature, you should start seeing a statistically significant uptick in this metric.

  2. Post-implementation productivity metrics

    A variety of post-implementation productivity metrics can be used to determine the effectiveness of your sales enablement strategies and tools. Some examples include the number of calls completed with an auto-dialer, the email engagement after leveraging workflows and sequences, improvements in data accuracy with a new contact database, and so on.

    There’s no end to the possible productivity related KPIs, datapoints, and metrics you could use, and it largely hinges on what type of enablement program or technology you’re analyzing. You can see some specific examples of that in the preceding paragraph.

    From the perspective of sales, marketing content’s productivity metrics are tied to the content share rate – i.e. how often is each new piece of non-gated content – such as pamphlets, brochures, blog posts, etc. – is shared with a contact in the intended market; and attribution reports. The latter provides information on how much each marketing content piece contributed to a won deal; thereby allowing you to determine which new content is most contributing to an increase in revenue.

  3. Lead-to-opportunity conversion rate

    As we’ve noted, sales enablement is designed to arm sales reps with the tools and capacity to speak more intelligently and expertly to a buyer’s individual, unique situation. This makes lead-to-opportunity rate one of the most obvious metrics to use when determining the effectiveness of your sales enablement programs and strategies.

    If, after determining through reinforcement that the sales reps have adequate enablement, and the conversion rates still aren’t increasing, it’s time to look again at what’s happening. One possibility is that the quality of the leads isn’t where it needs to be. Another possibility is to investigate whether they’re using their new tools in the sales process. After all, it’s one thing to know something – it’s another thing entirely to actively use the information you have at your disposal.

    You should also look at other causes if you don’t see a noticeable increase in conversion – particularly if things remain flat team-wide. Perhaps the information and knowledge you trained and reinforced them in wasn’t the right solution to address the causes behind the lack of conversion. If so, that suggests there was no deep dive performed prior to the enablement initiative – which needs to be done, whether you’re administering the program internally or using an outside vendor.

    We ourselves engage in those thorough discovery processes with our clients as part of our sales training process to make sure we’ve accurately identified the root issues and selected the appropriate solutions to solve those problems.

  4. Time to quota (can be further subdivided in percentage categories)

    This metric ties together a considerable number of metrics (conversion, win rate, average deal size, etc.) to provide a big picture snapshot of how effectively your knowledge and information enablement is progressing (and to a lesser extent, your other areas of enablement). After all, if your sales reps are now better equipped to deliver excellent service to your buyers, they’ll be able to close more deals in a quicker span of time (just how much quickly depends in part on your industry’s overall sales velocity).

    For high velocity industries, time to 100% quota might well be the most effective measurement – there’s a lot of churn and an expectation of a large volume of deals and revenue in a comparatively short period of time. For medium or slow sales velocity markets, you might want to look at time to 50% quota or even 25% quota.

    Also factor in where the sales rep is in their career. Someone just beginning their sales career will likely to take longer to hit those benchmarks than a tenured sales rep who is more familiar with selling and your buyers.

  5. Number and length of contact activities

    So far in this category, we’ve talked primarily about results-based metrics – or lagging indicators. As any sales manager should be able to tell you, that’s not necessarily the best way to determine the success level of your team members – particularly in those markets that aren’t high velocity.

    Instead, you should also look at – and arguably pay even more attention to – leading indicators – or the activities that will eventually translate into sales. In terms of measuring the effectiveness of your knowledge and information enablement, an excellent leading indicator is the number and length of contact activities.

    If your enablement is effective and working as intended, your sales reps will almost certainly be having more contacts with buyers – whether with the individual accounts, the overall number of contacts, or both.

    Furthermore, because your reps are now more knowledgeable and informed, the contacts they have with the leads, prospects, and opportunities in the pipeline should be lasting longer – particularly the calls and conversations (whether phone, in-person in non-pandemic times, virtual, or all three). Thus, length of time spent during each contact is another high-quality metric to use in determining this enablement sector’s effectiveness.

  6. Most important leading KPI attainment rate

    If you’ve paid close attention to your KPIs, you’ve likely identified one leading indicator that predicts the highest probability of a sale over all other KPIs. What that indicator is will obviously vary depending on your individual sales organization and team. But it’s an excellent metric to use for ascertaining the effectiveness of your sales enablement strategy.

Qualitative Measurements

Just as important as the data, however is the other half of effectiveness measurement – qualitative measurements. We’ve written a few times about avoiding the trap of being too in love with and too ruled by data in sales analysis, and the same is true about judging your sales enablement platforms.

  1. Evaluating calls and presentations

    This is one of the most effective methods to use – it allows you to review with your sales team what specifically is or isn’t working in regards to sales enablement. Whether it’s a rep taking too long to get a data field when intaking information, or a rep moving to the closing stage at just the right time to seal the deal, you have real-time evidence of things that are working well or need to be coached to.

  2. One-on-ones and sales coaching meetings

    This can come from or be part of the calls and presentations evaluation, or can be part of an organic discussion over how the sales reps think they’re progressing with mastering the sales enablement you’ve put in place. Regardless of its relationship to the first method of measurement, coaching and one-on-ones are the process by which you can help correct identified enablement-relationship issues or congratulate the reps on what they’re doing well. The best process, of course, will use both in the fashion that’s best suited to the rep’s communication style and preferred way of being coached.

  3. Being available for your team members

    It goes without saying that in order to accomplish either one of the first two items, you need to make yourself available to your team members. Sitting in your office and just reviewing data reports only gives you a very limited perspective on what’s going on. And while you could review calls, for example, on your own, that’s a missed opportunity.

    The missed opportunity? Having the opportunity to engage in collaborative debriefing with the sales rep, helping them to determine of their own accord what went well and what they still need to work on vis-a-vis enablement. It’s also a missed chance for them to ask you questions about the enablement and further reinforce and cement their own understanding of how a particular enablement strategy is intended to be used and benefit their skills, productivity, client service, and career development.

  4. Conduct conversations with buyers

    This might seem unusual for determining sales enablement effectiveness, but it’s an avenue to explore. For example, you could ask about a sales rep’s knowledge and expertise, or their response to particular pieces of marketing content they’ve been sent. Sometimes sales professionals get so focused on how things appear to be going internally in terms of enablement, they forget the real audience is the buyers. That’s who, after all, will decide with their pocketbooks whether your strategy is ultimately working or not.

    Also encourage your sales reps to hold those conversations with buyers as the prospects move through the pipeline. Check in and get an assessment of how your sales enablement programs are working that way, too. After all, you simply don’t have enough time in the day to talk to every buyer yourself. Let the team be part of the evaluative process as well.

As we’ve seen here, sales enablement comes with a wide array of possible criteria for measuring the effectiveness. Using these suggestions and tailoring them to the precise arrangement of enablement tools you’ve selected will allow you to see what’s working and what isn’t, and where opportunities exist to tweak your enablement so you can maximize your sales results.