Paul Butterfield
Table of Contents

Paul Butterfield, CEO of Revenue Flywheel Group, has over 20 years of experience in sales and sales leadership and 10 years in creating and implementing successful enablement strategies. He also produces and hosts the podcast “Stories from the Trenches.

Paul is also the Executive Board President of the Sales Enablement Society (SES), the oldest and largest non-profit organization for enablement professionals.

In this interview, Paul discusses the importance of leadership enablement, how best to work with frontline managers, and why aligning with the C-Suite’s financial metrics is essential. He also delves into the importance of enablement, Rev Ops, and product marketing working together.

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

From support to strategic

There's a lot of talk about elevating enablement today, which is healthy.

Several people are talking about operational versus strategic enablement. However, enablement doesn't work when split into two elements. They have to devise a strategy without operationalizing. If the enablement function is purely reactive or relies on random acts of enablement without a strategy, it will not have a long-term impact on the business.

Let’s assume your organization already has an enablement function that reports to the CRO or the Chief Sales Officer. Here's what you can do as an enabler who has been in this role for a while.

Take a step back and think about your existing programs or certifications. Has it had any impact? What has been the impact? That's a good starting point. You need to get anecdotal feedback if you haven't measured this consistently. For instance, if you can access Tableau, its features and functionalities could help you measure the metrics better. The idea is to create a correlation, one way or another.

When you go to the following step, you need to show tangible impact instead of saying, “I'm not having any impact, or I don’t know the impact.” Subsequently, you need to understand the top three financial metrics your CRO cares about and the metrics they are being measured on. These could be the board goals they have been given. Typically, there may be more than three goals. The reason to focus on three is that statistical studies have shown it's difficult to impact change management when doing more than that. That's where you start.

When you understand the goals, you can start thinking strategically about the building blocks. At a 50,000-foot view, what elements of your enablement strategy need to be in place to impact those revenue goals? Whether I am coming in brand new or doing a reboot, that's where I would start.

Starting in enablement, red flags, and green lights

Suppose you're looking for a new role in enablement; here are some things I would consider and ask more questions about. Red flags will vary greatly depending on the position you are interviewing for.

Where does enablement report?

While enablement not reporting to senior sales leadership may not be a deal-breaker for everyone, it would be a deal-breaker for me. It's not that I haven't worked with strong and brilliant Rev Ops leaders; I have. But in my experience, they are distinct functions that need to function differently.

New role?

I would want to know if this was a new enablement role or if the enablement function had been before. If enablement had been there before, was it broken? Was it unpopular? Was it simply party planning?

When coming in as a frontline or senior leader, there are many things you could understand about what's been done before. Whether a new role or a pre-existing one, what are the outcomes they're looking for with enablement? Why this position? What are the objectives? Talk to them about some of the financial or revenue outcomes they want to see.

The job description

Even something as simple as reading the job descriptions closely when you apply makes a great deal of difference. I've read many over the years, and with some of them, you can tell immediately that the organization isn’t sure what they want this person to do.

I see a lot of companies advertising for sales or senior sales managers. They're looking for an army of one or two people, but the job description runs for multiple pages. Be cautious of that.

Yes, you need a job. However, don’t set yourself up in a role where you're being asked to do things you don't have the resources or positive experience to do.

If they can't talk to you about those things, that would be a red flag. It means they haven't thought the enablement function through, which may not be a deal breaker, but it is a cause for concern.

Enablement, communication, and strategy mapping

It’s on enablement to help leadership catch the vision of their impact, how the business will run better and more profitably with specific strategies, not the other way around.

Enablers have to go and fight for resources. For instance, they need to go into QBRs and other environments with the leadership and help them catch commission.

Enablement is invariably selling at some level and helping people. It's the sale of ideas and research requests.

When you start defining enablement and assembling the strategic building blocks, you're also putting together how to measure against them. While we gauge many things in enablement, the first thing to calculate is how the strategy impact unfolds.

How often have you seen a strategy roll out with great fanfare, and six months later, nobody in the company can tell you what it is? That's why the scoring aspect of the strategy is critical.

Suppose you, your CRO, and other stakeholders align on the building blocks required to support and drive the identified revenue outcomes. Now, you can start discussing that with other internal stakeholders. By doing that, you're defining enablement’s responsibilities. What are the partnerships that need to be in place? While this is at a higher level, at this point, you haven't gotten into setting specific operational product programs. But that's where it begins.

When that's in place, find ways to consistently communicate with those stakeholders and meet them where they are. They probably won’t care how many people pass the ‘X’ certification unless there's an impact.

Let me give an example here. I got into enablement in Q3 of 2012. I was asked to leave my role as a sales director and learn how to build enablement by the new Executive Vice President (EVP). While it was complicated to measure impact back then, we still found ways to do it in 2012. Given today's digital and technological landscape, there's no excuse not to do it. Even if you can't afford the technology, the required strategy mapping could be done with MS Excel, if nothing else. Enablement needs to get better and smarter at strategy consistently.

It's that type of communication and scorecard that shows impact. This could include spending time in the QBRs or attending weekly sales meetings. For instance, it would be ideal if you or someone on your enablement team were invited to the weekly sales meetings. This will allow sales leaders and enablement to observe, discuss, and get feedback on what is going on with enablement.

If you're thoughtful, strategic, communicating correctly, and have a plan before jumping in, that’s a good start. Is everybody going to buy in? No. But, you'll always have some who still see the value of enablement, and you are putting yourself in a different situation and setting yourself up for success.

Changing enablement’s approach

While building a course in an LMS doesn't go away, it’s a means to an end, not the primary objective. Most enablers today are still doing some element of onboarding, though it's significantly scaled back. Let's start with what else you could be focused on. How was the onboarding for the different teams you support? What about DDRs?

While people think of commercial reps and enterprise sales reps, sales engineers are often forgotten. Enablement should not put sales engineers in the back room; that works during their first orientation. What is going on for sales engineers differently and separately? Because it's a very different set of skills, it’s not just deeper knowledge but understanding diverse processes.

Rethink onboarding

Look at your onboarding and determine if everybody is coming out of a cookie-cutter experience. If they are, the first thing to do is work with your leaders and stakeholders to determine what a ramping pathway looks like for that person.

Everyone could come together for 3 or 5 days for that standard onboarding. However, what are they doing after the first week for individual ramping? There will be an overlap, but they should also be unique. For instance, DDRs may have a 10-day ramp period, while sales engineers might have a 6-month ramp period. Unless the individual onboarding is established, figuring out everboarding can be a challenge.

There are multiple ways to find and create competency frameworks and mapping online. This works for small and large groups. For instance, something as simple as making a spreadsheet would work better with a smaller organization.


Across the top of the spreadsheet, list the skills you and the leaders agree on based on the sales stage. For instance, a rep must execute stage one through to the last. Now, on the left side, list the reps, and with their names, add a couple of simple formulas. This system will make it easy for your leaders to create heat maps.

Suppose your leaders are figuring out the competency framework for Sue Jones. Top line, go across, you give her a 1, 2, or 3. Then you get to the skill boxes, into which the formula is built, which will turn them red, yellow, or green.

Heat maps are a simple way to determine where the current group is and what enablement can do. “Here are the professional developments we need to pick up.” Start with ensuring reps get a good foundation when they're coming in, and then figure out what long-term professional development entails.

Leadership enablement

While companies today are doing less onboarding, there are also fewer people on the team. Leadership enablement is another overlooked area. Revenue leaders need it as much as anybody.

One of the most common stories in sales is a Rockstar rep gets a promotion and has to manage multiple reps. Because they can't clone themselves, they become super-closers. Often, they have procedural training. However, when new leaders are brought in from the outside, they don't go through the same onboarding as the organization's sales reps or marketing personnel. Why not? If they're a VP, you need to make that a customized experience and get them meetings and resources that they would need.

Conversational intelligence is one of the most significant advances in looking at leading indicators within enablement functions for both sales leaders and coaching purposes. Leading indicators were always one of the toughest to figure out. Conventional metrics are helpful in this regard. For instance, how quickly did they get to full-funnel coverage? How fast can they do their qualified close-up?

Other leading indicators like behavior also need to be considered. Conversational intelligence can help determine if reps are using the correct language. It’s just as important not to confuse buyers by using excessive jargon. This doesn't help them see your company's position and value proposition.

Here are three things to help you do the correlation in more sophisticated ways:

  1. Conversational intelligence
  2. Building scorecards
  3. A good enablement platform

Frontline managers, feedback, and building relationships 

First, figure out if your frontline managers have been equipped with the skills and abilities to be the effective change agents required. The next step is getting frontline managers involved. It's always a dance between getting feedback and being unable to incorporate everybody's feedback because it often contradicts itself.

It is giving people a voice and trying to understand what's going on. Most people understand you can't improve everything. You're on track with the executive team as long as everything's mapping to one or more of your CRO or CSO's top 3 revenue outcomes. It also helps frame that conversation with frontline leaders.

You want us to do an X training? Let's look at that holistically. What are the outcomes you're looking for?

Have your frontline sales leaders ever been taught, for example, the difference between coaching and pipeline review? Do they understand how to look at a pipeline in a more sophisticated way?

Often, you'll hear, “2.7 x, that's our ideal pipeline coverage.” That's great. But if 90 percent of that is in stage one or two and you're in the third month of your quarter, you're in trouble. How do you determine if they know how to look at that in a more sophisticated manner?

Often, they don't know the outcomes they are expecting. Having a serious discussion with them can help here.

Leaders and rollouts

There are some things that only a frontline leader can do. For instance, as a sales leader, I’d want to see someone's pitch before they took it out on the street. No offense, but I didn't trust someone else to tell me the pitch was ready. Enablement needs to figure out how they can support the rest of the ecosystem required by sales reps.

Let’s assume you're rolling out something new - a tool or a methodology. Something I haven’t seen happen in enough organizations is walking the leaders through it first. Let them be comfortable with the tech or the methodologies in a safe environment with their peers. While asking questions in training settings is risky, most people won’t do it in front of their reps. So, give them a safe peer-to-peer learning environment.

In this case, don't leave it to reps and frontline managers to figure out how to reinforce it in their sales meetings. Suppose you have an 8-week playbook that includes prep for weekly sales meetings where managers will discuss X. Give reps exercises, role plays, or things to run through. In an 8-week cycle, reps can be refreshed on everything their team learned in the recent methodology pullout.

Think about the things reps have time to do and the things they are asked to do that have nothing to do with helping them close deals or get better. As enablers, we must consider the critical things a frontline sales leader can do. These include pipeline review, one-on-one coaching, deal reinforcement, etc.

Enablers will never have 100 percent buy-in from the group. However, when you are building those relationships, working, and able to document results, it becomes a no-brainer. While the sales leaders may not wholly agree with what you've done, they may agree to disagree if you are getting results for the team.

Enablement and Rev Ops

The right way is not to have the enablement function report to Rev Ops. They are separate, parallel functions. These two departments must report to two leaders at peer or close-to-peer levels. However, that alone doesn't solve the problem.


A significant area of overlap is technology. For instance, any technology the enablement team might be evaluating could impact Salesforce or any other system for which Rev Ops is responsible. They need to be involved in that process. Suppose you're looking at three vendors; narrow it down to one and begin due diligence. Bring Rev Ops in before that point because they will have opinions.

Suppose you are looking at X company for conversational intelligence tools. It is going to be a Rev Ops decision to bring them in. However, who will teach these teams how to use that tool? How to read the dashboards? How do they run the reports? Enablement needs to be involved early in those conversations to build relationships with the CS teams.

For instance, anytime I buy technology, I let the vendor CS teams know that they are on the hook with serious skin in the game if we roll this out. Once they teach my team how to do the frontline support and training, they may be off the hook to some extent. But during deployment, it’s all on them. We're here to learn and work with you. If you can build those relationships early instead of suddenly saying, “Hey, we're rolling this out next week and you're going to need to train us on,” you are off to a good start.


The other considerable overlap is data. Most enablement organizations don't have the ability to go in and get their correlation data. They may have figured out:

  1. What they want it to be
  2. What they think it should be
  3. How should it align with sales leaders (and, to some degree, the Rev Ops teams)

However, enablement teams often depend on getting that data pulled from Rev Ops.

The three-legged stool

It's critical to have excellent working relationships with your stakeholders. My concept of the 3-legged stool consists of enablement, Rev Ops, and product marketing. Without one of the other, the stool will just wobble.

That relationship should already be a key one that you're working on. However, enablement needs to be sensitive to the fact that Rev Ops often gets a lot of demands from the board, especially if you are PE-backed. These folks typically want to see that data carved up in a thousand different ways. Any request you have, get those in early or find ways for them to help you self-serve, build dashboards, and Salesforce.

Be sensitive to the fact that they often get considerable additional demands with little notice, and build that relationship. That's when the overlap comes in the form of data. Suppose you have the luxury of getting a tool on a platform that integrates with Salesforce and can do that for yourself, great. For instance, our Rev Ops team built the ‘One Ring’ inside Tableau, where you could find anything you wanted from a sales data perspective. It was one of the best tools I've ever seen and the only time I've ever used something like that.

About the author


Paul Butterfield

Paul Butterfield, CEO of Revenue Flywheel Group, has over 20 years of experience in sales and sales leadership and 10 years in creating and implementing successful enablement strategies.

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