Scott Powell
Table of Contents

With over two decades of expertise across Sales, Strategy, Operations, and Enablement, Scott Powell is the co-founder of EnablePoint, where he leads Go-To-Market Enablement teams on a mission to increase sales productivity.

In this interview, Scott talks about data-driven enablement, how enablement needs to go beyond onboarding, and the best way to orchestrate the enablement initiative. Drawing on his wealth of experience, Scott discusses the role of enablement during a recession. 

(This conversation has been edited for length and clarity.)

Supporting Reps Beyond Onboarding

So many organizations see enablement as being responsible for boot camp or on-point training. However, one of enablement’s goals should be to go beyond boot camps to create an environment conducive to continuous learning. 

For instance, when I was at Cloudera training their team, I created this spectrum from new Hire to Quota. Training new hires is what people associate with boot camp and onboarding. Assuming that just goes away due to the current economic headwinds,  that still leaves a whole lot left to include in ongoing training. 

Ongoing Enablement

The role of ongoing enablement, when companies are not hiring reps today, consists of training. This training ranges from certification, QBRs, and SKOs to product trainings, win-loss analysis, and more.

Certification is the flagship of ongoing training— proving and validating knowledge. My enablement teams have frequently run not only launches but Quarterly Business Reviews or QBRs. Building a proactive team starts with getting involved with the sales leaders and finding out what's working and what's not. We are linked at the hip with product training, especially regarding certifications.

Competitive intel will make a world of difference, especially during a recession. When I was at Optimizely, we would produce 15-minute videos each week to support and validate training. For instance, we did a video on Valentine's Day about why we love our product. These consisted of short snippets from different leaders, after which we did a win-loss analysis.

We even discussed them openly on weekly calls with the deal teams and then surveyed the field to understand what was working and what was not. 

Strategic Enablement

The role of strategic enablement when companies are not hiring reps today consists of the following: 

  1. Account discipline is the act of figuring out which accounts you're not going to go after. In many cases, sales teams are chasing way too many accounts. Which ones are going to get into your following number? Enablement can then help reps around those accounts.
  2. Leadership training. 
  3. Lifecycle Development (e2e) ensures that all the things listed under ongoing and strategic training fit together. This means what your customers see is consistent with your certification. 
  4. Playbooks are a one-stop shop where new or tenured reps can go and find everything they need to include, such as competitive intel, discovery, etc. For instance, at Optimizely and Handshake, we developed playbooks based on a specific industry or persona.
  5. Sales methodology frequently falls under the responsibility of enablement. 
  6. Stakeholder Input. Interviewing your key stakeholders periodically about what their needs are is essential. Refrain from assuming everybody knows. Everybody talks about it, but who's capturing it? 

These are all critical roles that are enablement’s responsibilities to deliver.

Cost Center Vs. Cost Multiplier

Here’s how you can elevate the role of sales enablement with the C-suite when many of the support functions are being cut.

A seat at the leadership table

Ensure that you have a seat at the leadership table with the CRO and other C-Suite leaders and understand their needs. Ask yourself: 

  1. Are you attending the forecast calls? 
  2. Are you meeting with the go-to-market (GTM) leaders regularly?

Articulate the value delivered

Be clear and tell them what you are bringing to the table. Often, enablement leaders assume that everybody knows what their team is doing and is aware of their value. However, during hard times, enablement is seen as a cost center. 

Align future metrics

Is there alignment between the metrics you are using to measure the enablement function and the metrics the C-Suite is using?

When it comes to aligning your future metrics to those of the C-suite, have a conversation about how you're measuring the business, especially with the CRO, and get them involved in the enablement roadmap. 

Enablement Roadmap

When putting together the enablement road map, it’s essential to be part of the C-suite plan and incorporate it into your planning. Enablement roadmaps let people know what's coming and articulate the value your team is bringing. 

Enablement KPIs

Here are some examples of enablement KPIs I have used in the past. 

Enablement KPIs Definition or Formula
Sales Rep Ramp Time New hires are typically at their full productivity
Average Productivity Bookings/Ramped Reps
Time to close the first deal
Participation The number of reps at or above the quota
Contribution The percentage of people who have closed at least one deal in a given quarter
Time to 4x pipeline Sales reps’ generated pipeline
Conversion/Win Rates Number of opportunities/Deals closed or won

Sales KPIs 

These are essential when doing cross-functional work with both Sales and Sales Operations. 

Sales KPIs Definition or Formula
Average sales cycle Total days in the pipeline for closed deals / The number of deals closed
Average sales price Time opportunity ⇒ Closed or Won
SPIFF attainment Percentage of qualified reps
Sales Rep Tenure Average time in the seat
Sales Rep Attrition Exiting reps / Total reps
Annual Contract Value Total Contract Value / Contract years

Something not listed here is the ratio between new and existing businesses. We can't have a leaky bucket, so we need to ensure there is enough existing business to keep the lights on and ensure recurring revenue.

Orchestrating the Enablement Initiative

There are three goals in enablement. 

  1. The enablement team is the customer success team for those going to market. So, enablement supports customer success, partners, BDR, and SDR functions. Their success is our success. Enablement is compensated in multiple roles. On the success of the GTM teams, for instance. 
  2. Create an environment of continuous training directly relevant to your customer and your discussions with the specific team with a non-boot camp approach. You need to ensure things are certification-relevant, in real-time, not past their expiration date, and it's replicable. If you do it for sales, you can repeat it for the sales success team and create raving fans of the enablement team with those GTM leaders saying, “Enablement treats me like a customer. They deliver continuous enablement and design the programs with me. It's simple, and this is why we love enablement.” 
  3. Ask what they need. For instance, you go to a sales leader and ask them what they need.  After they tell you, you make it for them. You design and roll it out together. “In this month, we're all gonna do the training, and then at the end of this quarter, we rinse and repeat, make improvements, and roll it out again.” That's a great cycle to develop with your GTM leaders.

Defining the initiatives and the metrics and aligning them is essential before starting an enablement initiative. Enablers need to be people reps want to see and speak with, not be associated with, “Oh, god, here comes some more training.”

Another aspect is going beyond sales. For instance, whenever there is an event or a function, like a launch, I always survey the team afterward. If someone comes back and says, “This was too sales specific,” then we had not taken care of that team or constituency like the customer success team. Unlike past enablement teams, my existing teams are primarily people with past customer-facing roles and credibility with their go-to-market leader, with a customer success enablement manager who was a customer success manager.

Role of Enablement in a Recession

Amidst the current recession, enablement support is required more than ever. Now more than ever, the role of enablement in an economic time like this comes down to the following:

Increased support and training

With the current economic environment, cutbacks have led to smaller teams in enablement and across sales. These cutbacks have led to territories and quotas getting bigger for reps, increasing the need for support and training. 

Reinforce learning

Companies invest a lot in their reps. For instance, if they are running training through a vendor, it’s not cheap. It can be very effective, but it needs to be reinforced over time.

If the enablement team is not on top of this, who is? 

This means companies spend a great deal of money on something, only for it to lie unused a year later. The real test is if it’s being applied in the one-on-ones between managers and their sellers. 

Validate knowledge and skills

Are you testing reps and go-to-market teams on what they know, or are you assuming they know the product? Enablement can reinforce skills to be consistently applied and validate the necessary knowledge and skills. 

Support at every deal stage

Are you assuming that reps know discovery and prospecting? Not just new reps but tenured reps also need support at every deal stage. No rep in any organization is perfect at every deal stage. 

For instance, senior tenured reps may need more help with discovery or prospecting. Supporting reps necessitates a one-on-one, tailored approach. The intent is to do a concierge or a white glove approach toward everyone to find out what they need and then deliver it to them. The one thing to avoid is the one-size-fits-all approach.

Data-driven Enablement

According to the 2022 Enablement Landscape Report, the most common ratio of enablement to reps is 1 enabler for 25 reps. If companies are cutting back significantly, your enablement team is probably supporting more than 50 people per enablement manager or by themselves.

In this situation, your team will be forced to do triage. Such a situation boils down to enablers working on the fundamentals instead of strategic enablement. Companies need to be careful if they cut back too far. At the moment, despite enablement teams are getting cut, initiatives still need to be completed. Because while companies may have cut back on enablement teams, the revenue targets have stayed the same.

However, there's no one left to do them because companies did not stop to consider the adequate ratio of enablers to the people they support. In a world where reps must win every deal, here is how enablement teams can up-level skills and make them more effective:

Seller Health Check

There are two main steps in performing a seller health check. It all begins with understanding at what level reps are at and figuring out how enablement can drive their success. 

Knowledge Validation

Suppose one of your top reps still has gaps in their skill level. 

First, you must validate their knowledge from the fundamentals to proven critical knowledge. Both the rep themselves and the managers need to assess their level of knowledge. Before asking for enablement, check the required level of understanding so that everybody seeing a specific concept or strategy at that moment has heard it before. Ensure reps are certified on the product, the process, and the systems. Often, enablers think reps need to be certified only on the product. 

a. Are they knowledgeable about the sales process? 

b. Have they demonstrated mastery of the sales motion adopted by the company?

c. Do they know their systems? 

Some people need help with the systems they use for prospecting, but they might be afraid to ask. It's validating they know that, and nothing is more reinforcing than reps demonstrating that specific knowledge in front of their peers.

Solution presentation certification in front of their peers is one of the most effective ways to make reps do their homework and get that level of mastery.

Power of Four

It's all about a flexible support team. Now, your reps are doing self-assessments. The manager looks at their pipe, deal quality, and areas of expertise and assesses the development the rep needs. That's where the next person comes into the picture. 

Subsequently, the enablement team member identifies what is required, supports the rep based on their specific needs, and delivers what's required. Something frequently overlooked is demonstrating what good looks like through a proven peer. You have to be careful. For instance, with a tenured rep, you do not want to bring someone in to say, “You're not doing it right. This person knows how to do it.” 

Instead, make it more of a collaborative exercise in which a proven peer shares how they did their prospecting and discovery with the group. Additionally, we have inculcated a practice in our weekly team meetings where sellers and the entire deal team would stand up and talk about how they won, not that they won. Sharing that knowledge is critical to ensuring that people understand what good looks like.

Reps love the limelight and are very competitive. Enablement needs to gamify their success by showing them what good looks like. Other reps will think or say, “Well, I need to be that good, and that's what I want to match what good looks like.” 

That's how reps can achieve success and how enablement can help make that happen.

About the author


Scott Powell

Scott Powell is the co-founder of EnablePoint.

Subscribe to Elevate,
our bi-weekly newsletter.

Get the most interesting stories from the world of sales and revenue enablement every alternate week.