How do I measure sales enablement success?

I’m going to answer this question the same way I answered, “How do you measure ROI of sales enablement?” because ultimately success should be ROI in some form. Here’s my response again: 

Ultimately you want everything to tie back to revenue (usually in the form of new versus growth versus retention), but you can never fully hold PMM accountable for those top-line numbers since there are so many other forces at play. This is why you need a set of secondary metrics you can use to measure your efforts a little more directly. For starters, measure the attendance rate of your sales enablement sessions, measure the views/downloads of the content from it afterward, and run quick surveys to measure the effectiveness of the session (even a one-question 1-10 satisfaction survey will do). Next, look at the metrics that you have more (maybe not full) control over that should ladder up to revenue. Are win rates increasing against a certain competitor? Are there more in-quarter sales-stage progression of deals? I love this one because a deal may not close for a number of reasons out of your control, but if you can say “we moved X% more deals from discovery to solution validation” (or whatever your sales stages are), this is a powerful metric.

It really depends on the type of enablement that you’re doing and the problems you’re looking to solve. But at the end of the day, there are two key metrics I’m always looking at, which is the average contract value (in conjunction with number of deals won) and the win rates. In addition to looking at whether there’s a measurable increase/decrease, there are other factors I assess:

• Consumption of enablement materials: What % of the field has been trained? And how are the materials being used in prospect conversations or follow-ups?
• Gong calls: Not everyone has Gong (software that enables you to analyze recorded customer-facing interactions), but if you do, it’s an amazing way to hear whether sales has effectively absorbed the enablement material and leveraging it properly with prospects
• Sales feedback: I usually have a set of go-to reps and sales managers to get quick feedback on how something is resonating with the sales team. I also like to leverage surveys, but more so on a quarterly basis to assess confidence in core areas and how that changes over time based on dedicated, focused training in trouble areas
• Win/loss analysis: We leverage Clozd to conduct impartial customer interviews, and help us understand the reasons behind why we win and lose

A shorter answer here, but I think there's a pretty straightforward way to measure sales enablement overall. Ideally, this is driven by the sales enablement team, and you're fueling their succces:

Key metrics to measure sales enablement:

1. Rep ramp - How long does it take new reps to onboard and reach full quota? What is the success rate in that period?
2. Annual quota attainment - What % of reps are at or above plan? Does it match the business needs?
3. Win rates - How effective is sales at qualifying, develping, and closing opportunities?

Win rates is probaly the most complex to measure. Looking at your current sales process/buying journey, where are there friction points that PMM supports? I like looking at conversion from a Sales Qualified Opp to trial or proof, and then Proof to Close, but YMMV.

My top 3 metrics to measure sales enablement success are :

1. Reduction in ramp time for new AEs coming into the company - defined as 'how many days does an AE spend at my company before they close their first New Business deal?'

2. Quarterly rep participation rate - defined as 'what % of my ramped sales team closed a deal this quarter?' - this number should increase every quarter if your sales enablement program is effective. If your sales cycles are close to a year long, then perhaps you evaluate participation on a bi-annual basis (2x/year). If your sales cycles are much shorter (less than a month), then evaluate on a monthly basis. But the same concept holds.

3. Win rate by segment and by region - defined as '# of deals closed-won divided by # of deals closed in a given period' (usually quarterly). It usually makes the most sense to look at deals that reached a certain stage before they were marked closed (I like picking the earliest stage after an opp has become a "qualified opp" - this is usually Stage 2 or Stage 3 in a typical sales pipeline).

4. (bonus) Average selling price - this metric effectively measures how well your reps communicate the value of your solution to prospects, which comes right back to how good your enablement program is.

I personally don't care for attendance or competence metrics such as "which of our reps attended this session" or "how many of our reps passed a quiz on this topic?". The vast majority of the AEs I've worked with are highly competent, well-trained professionals. They tend to be pretty good at managing their own time, and these metrics feel a little too "nanny state" to me and I don't think they correlate strongly to actual performance. 

The other problem with attendance or competence metrics is that they don't tell you whether the content for the sessions is terrible, which happens a fair amount. I've seen too many 40-slide word vomit decks masquerading as enablement - they're not, and many of these decks create more questions than they answer. If I was a rep, I wouldn't show up to those sessions either.

Final word - because this is an important question. When you want to understand the effectiveness of your sales enablement efforts, always measure business results, not activity. You'll identify issues much faster, and you'll get a lot of joy out of watching new and ramped reps win more deals.

I think there's a similar question above on measuring KPIs. Please refer to it. But essentially I'll look at 2 parts 

1. Whether sales has received the information

• Attendance rates, Tests/Quizzes to capture main points, engagement rates during the training, feedback post the training and % of sales force trained

2. Whether sales has activated post the training which might take longer

• Adoption of product/recommendation 
• Revenue growth attributed to the product 
• No. of clients pitch to
• Higher win-rates

It's a bit of a white whale in a lot of organizations, but ideally you want to measure not just consumption or certification rates, but the percentage of closed/won opportunties in which the account team directly applied a specific enablement program or content. If the assumption is that sales people who are sufficiently enabled on customer needs, the market and your solution win deals at a higher rate, faster and for larger dollar values, then any sales enablement measure would ideally track those outcomes. Often sales enablement measures are very "top of the funnel" in that they track the percentage of sales personnel who've either completed or passed an assement on a given pitch or value assessment. Sometimes there are utilization measures that track how often certain content is accessed or programs applied by sales teams during an opportunity's lifecycle. These methods seem to be how most organizations measure sales enablement succes. However, in my opinion, companies should measure sales enablement success by the impact enablement has on closed/won opportunies. Did this enablement help the team win the deal faster and at a higher dollar amount than if the team had charged forward without any enablement? Sales enablement is best measured via cohort analysis rather than incremental consumption or utilization measures. 

• At a high-level the goal is likely to make sellers more productive in some sense. Probably by making them more effective or more efficient. Let’s just call this “go-to-market readiness” as this is typically a key pillar of any sales enablement team.
• GTM readiness is likely the success metric that is going to be most inspected/cared about. So you’ll want to be tracking things like time to close, deal velocity, deal size, churn (if trial to close), or any other metrics that are standardized and easily reportable via your CRM. Other GTM readiness metrics that would be especially relevant for orgs that are quickly growing include things like time to ramp for sales reps (could be measured by testing/quizzing for proficiency in combination with quota attainment), % of reps at quota, etc.

Create a quiz or set up role playing for your sales team on their understanding of the product features, capabilities and messaging. When you set aside time to observe how your sales teams are understanding and consuming your sales enablement, you create a better relationship with the team, and know which reps may need more help in what areas. By watching how well the reps could talk through the key messages in a role play, or through their quiz answers, I know what was working and what wasn’t.

Sharing how I think about this as an industry marketer. My first step would be to huddle with my sales and product leaders and align common goals (where possible). If you are working within a larger organization, perhaps start by collaborating with your sales strategy, sales programs and sales enablement teams, then up the chain to sales/product leadership. 

In addition to business outcomes (ARR, etc.) you'll want to leverage the collaboration with these teams to determine the enablement program strategy and design. What knowledge do we want each seller to have based on role? How do we want to measure knowledge retention? What channels do we want to use to teach (live webinars, LMS courses, in person hands-on training, recordings, or train-the-trainer)?   

Having data is critical for measuring success so the design of your CRM greatly impacts your ability to measure and improve outcomes.

Another element is the design, roles and coverage model of your sales organization. Do you have geographically-aligned selling teams (vs. vertically-aligned) where each account executive’s focus is split across accounts in multiple industries. Knowing up-front how much mindshare you will have from each seller is important to set your baseline for focus industry success.

Here are a few tips on measuring enablement success by role.

For junior sales representative fielding inbound responses, the measure you may wish to track is qualified leads. If you are able to capture interactions (chat, email responses, etc.) you can analyze the records of those interactions to help train and improve how the junior rep responds effectively.

For an inside sales team making outbound calls, you may want to track conversions to meetings, and observe their calls to understand common objections and help the BDRs develop messaging scripts that improve their success rate flipping meetings to AEs.

For account executives, you may want to track contact engagement within the target set of accounts, and the creation of new sales opportunities a period of time after specific enablement training is given and selling motions commence. 

For sellers that are product / solution specialists, you'll want deeper enablement materials and track knowledge retention through an LMS or 'stand and deliver' or vision demo build competitions.

To scale globally, you’ll likely need to rely upon a train-the-trainer model that can jump the geographical and language barriers. Measuring LMS course completions, downloads, shares, and attendance of regional enablement events are several ways to measure success abroad.

There are a lot of ways to measure sales enablement: lead-to-conversion rates, win-rates, sales rep NPS, etc. HubSpot does a great overview of popular options in this post. 

In my experience, there is no one-size-fits all and getting to the "right" answer requires a deep understanding about how marketing and sales contribute to your business. In the end, it's all about alignment (with sales) and impact (for the business).

If you're starting from scratch (e.g. new business unit, early-stage startup), I recommend working with your head of sales to define success. In the short-term, it might be about unblocking common objections with great content (e.g. a competitive one-sheet or a deep dive on a product differentiator). In the long-term, it is your job to stay aligned as things evolve and start measuring the impact your work is having on the pipeline. Even with a small sample size, you can try to cater your work so you can answer questions like:

• How often has this asset been seen?
• How often is it seen by someone in the sales pipeline?
• Is there a difference for the AE when a prospect sees it (is it easier to sell)? Is there a difference in outcome (are we more likely to win)?

I've worked at companies that had various approaches to sales enablement goals, but in every case it was eventually crucial to tie the work we did as close as possible to revenue impact.

In my opinion the effectiveness of sales enablement should be measured by reducing the customer acquisition costs over time and reducing the time it takes to close a deal. Having these in-process KPIs that you can track month over month will help you demonstrate how your enablement activities are helping sellers meet their quotas. 

As an industry marketer I am mostly concerned around the sales cycle, ASP, win rate, content performance, and rep productivity. Good enablement, marketing, and content, should shorten sales cycles and drive how things are leveraged ie case studies, whitepapers, solution briefs, and blogs.  

Often times good enablement will measure these variables continuously on a rolling basis and will work closely with industry and product marketers in understanding training gaps.

I've seen this done successfully a number of different ways. Here are a few common ones:

1. Usage - What is the % of your sales team that is using the content and collateral you are creating. If you use a competitive enablement tool like Klue, you'll be able to track usage and adoption of things like battlecards and digests.
2. Win Rate - This one is simple. What is your win rate against competitors prior to your enablement initiatives. How much does it increase post enablement initiatives? My recommendation is to start by trying to move the needle on one or two competitors at a time, rather than taking a blanket approach.
3. Confidence - How confident is your sales team in selling your product today? How does this confidence score increase post sales training or other enablement initiatives? 

I find it particularly interesting to link Usage Rates back to Win Rate. If you can connect the dots to show that sales reps that use your enablement material have higher win rates, you'll not only be able to prove the success of your programs, but also use that information to encourage faster adoption amongst the rest of the sales team too!

Sales enablement success should ultimately drive sales success, including the size & number of deals closed won and win rates. Leading sales enablement indicators of sales success include adoption of content, sales feedback, and feedback from prospects/customers as part of win/loss analysis. In particular, if messaging is done effectively and rolled out properly to the sales team, then the win/loss analysis should show that the messaging ultimately resonated with the prospect upon deal close. Before that even happens, product marketers should be able to see that the field has either downloaded or otherwise used the content (content adoption) and usually provided positive feedback on the content based on how their prospect conversations or current sales cycles are going. 

Measuring sales success is unique to your organization but you can gauge general effectiveness by understanding the volume of opportunities, conversion rates, and productivity. 

Volume of Opportunity
Cross-selling, renewals, and upselling are more effective ways of generating revenue than acquiring a net new customer. According to InsightSquared, the average cost of acquisition for a company to renew a product is $0.13, the average upsell costs a company $0.28. Both are dramatically more cost-effective moves than acquiring a net new customer—at $1.18 to earn $1.00. 

These cost-effective sales motions require the ability to sell value and solutions. You can gauge if your sales organization is selling solutions by creating value-oriented messaging seeing if it’s used by them during conversations. The lead-to-customer conversion rate is a gauge to see if your message is being used and for the overall efficacy of your marketing and sales funnel. 

It’s not enough to create compelling content—you need to make sure your sales representatives are using it. They are the ones using your tools in the real world, during conversations with customers in order to convince them and to address their objections. Through interviews with individuals, you can get feedback on what content is particularly useful. Through tools, you can understand the most effective content and the content leveraged by the top performers in the organization as well as by prospects themselves.

Conversion Rates
It’s not enough to talk about value. Your content should help the sales organization to talk about how your company delivers differentiated value. Closely looking at win/loss rates against key competitors and the context around these ratios can reveal gaps in sales, marketing, product, and customer success strategies. 

For example, if you have a low win-loss ratio for the cloud segment of your business for prospective business customers with 500-1000 employees, that may be indicative that you are not offering differentiated value for that market segment relative to the competitor. Doing this exercise can inform you of the need to create more targeted objection handling content, more training collateral for that segment or vertical, or may highlight a larger issue with product or GTM strategy.

Productivity
In order to scale your company, you need to reduce the time it takes for an average sales individual—without the expectation of domain expertise—to quickly ramp up without much hand-holding. For measuring the ramp up time for individual representatives, you can look at the time it takes for them to close their first deal or meet their quota. On a macro level, reducing the time it takes for individual representatives to get up to speed reduces the average sales cycle itself.

My favorite way to measure sales enablement success is through a Sales Confidence Score. Start with a baseline survey to the sales team on their confidence across your products, personas, verticals, etc. Take pulse surveys after each enablement session and then make changes to your programming based on their confidence.