How do you measure sales enablement success?

Below are just a few metrics that are useful when tracking sales enablement success:

Lead-to-opportunity and/or lead-to-customer conversion rate. If more leads are converting to opportunities over time, and/or if more leads are converting to customers over time, then Sales is getting better at delivering the right message and closing their deals.

Competitive win rate. Overall win rate is good to track, but that depends on many other factors. Competitive win rate is more specific to the content and enablement that product marketing and sales enablement produces, and if you work with your Sales Ops team to get a few dashboards set up in SFDC, you can track QoQ whether you’re improving your win rates against top x competitors.

Content usage. We’ve used Highspot in the past, and it’s great for tracking views, downloads, shares, etc. for sales materials. If the material I’m putting out there for sales is getting used, great! If not, we should understand why.

There's a lot that goes into effectively measuring success.

• Defining what success looks like ahead of time (e.g. what KPIs you're trying to influence) 
• Recognizing that the definition of success will look very different depending on the initiative (e.g. a messaging overhaul of an intro proposal might have % of reps passing certification as a KPI while a product launch might have attach rate as a KPI)  
• Making sure you have a means of measuring that KPI (e.g. closed/won opportunities in Salesforce; auditing a random sampling of customer calls). 

Success measurement can frequently break down because the definition of success is determined post hoc rather than before the initiative was developed; there are gaps in data systems; or teams haven't set aside sufficient time and resources to get in the weeds of measurement.

This will depend on how do you define sales enablement at your company, but I will break it out into different categories and all of them combined will lead up to revenue or moving pipeline. 

(1) Product training - are reps learning the right messaging and is it landing? You can measure this category in two ways. Leveraging a tool like Chorus.ai or Gong.io, and create trackers on the product and key messaging that you want to track. You can measure how many reps are using your messaging for said product and how well it lands with prospects. On the CS side, you can track the same, and depending on type of release - product adoption and upsell. 

(2) Sales training - are reps deploying the right strategies whether they are competitive strategies, middle funnel strategies to move the deal forward? I would leverage trackers, but also feedback from sales managers. 

(4) Content - You should leverage a tool like Highspot, ShowPad, or similar tools to see the types of content being leveraged by reps and the types of content that are effective with prospects and customers. 

(5) Sales strategy - Is your approach the right approach given the market and persona? How does this translate into the selling motion? Does it reflect the buying motion? Do you have a middle funnel problem where things stuck? Do you have the right advice and CONTENT for each stage of the sales process and sales stage? The main measurement here is sales velocity for New Business. The main measurement is for CS is how effective is your customer journey and do you have the right CONTENT and tool for your CS team to upsell, renew, and increase retention. 

I hope this helps. 

The best framework I've seen that works is the Kirkpatrick pyramid to measure enablement (really training of any kind) effectiveness. It starts (1) are they happy? Typical measure: CSAT (2) did they learn anything? Typical measure: assessment (e.g. quiz/certification/etc.) of some sort (3) did that change behavior on the job? Typical measure: manager ride alongs & feedback loop (4) and finally the ultimately nirvana of a goal: did that behavior change drive the revenue needle?

Most teams, including mine, have never made it past 2.5/3 because the complexity in enterprise deals makes it hard to pinpoint one single behavior change to drive a complex deal forward. So really if you can get past 1, and measure assessment, you have some leading indicators of AE performance & business performance.