Ashley Philipps
Table of Contents

Ashley Philipps, our guest for this episode, is the VP of Commercial Effectiveness at EverView (formerly Output Services Group). Ashley has a background in teaching but has been passionately involved with enablement for the past eight years.

In the interview, Ashley talks about how the onus of elevating the role of enablement lies with enablers themselves. She also suggests we shift our focus from generating pipeline to retention and expansion in the current economy when landing new deals has become more difficult for many organizations. 

Please read ahead for more.

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

More strategy, less support

Elevating enablement to a strategic role requires enablers to do it themselves. 

At their core, enablers are problem solvers. So, we often tend to take on a tactical or support role from the beginning, leveraging our expertise in specific niches such as enablement, customer success, relationship building, and so on. While that’s great, we’ll struggle to elevate ourselves and earn a seat at the table if we don't teach ourselves all aspects of the business.

Ask yourself - what are you doing to improve your business acumen? How are you growing as a person in business across sales, people management, and leadership? 

As an enabler, you can set specific priorities if you’ve access to data. Are you doing that, or do you make a task list and become a people pleaser by delivering? 

At this point, you've convinced yourself and others that this is a support role. 

Say you are new at your job. You might be spending a lot of time on listening tours. These are double-edged swords. Asking your top sellers how they do business can give you good data points to help you set your priorities. But you may also end up with a task list of sellers asking you to ‘fix this asset’ or ‘add a slide there’ and so on. So, you may end up becoming an ‘order taker’ and a ‘people pleaser’ working to get that task list done. 

There's nothing wrong with listening when it works. For example, you want to know what the field is saying and doing is aligned to the organization’s revenue targets. Enablement can then enter the room and say, “We’re hearing this. People are doing this. This is our goal and here's our strategy to get us there.”

If that's what you do on your listening tours and conversations, great. Unfortunately, the buck often stops at “I didn't get around to strategizing or streamlining the process, but I did deliver a few assets.” 

Also, many enablers say, “I’m not the decision maker. I might be able to pick the engagement tool and enablement platform, but I don't have a say in anything else. You will be better off contacting IT to get new software.”

It’s time to change this narrative.

Enablers have to be very careful about how they position themselves in the organizations. Give yourself enough space to have strategic conversations and find mentors and allies elsewhere in the business.

Enablement should be the ultimate connector. It will make an enormous impact if you're connected and working on multiple projects outside of sales. When cuts are being made, the more that you have shown you're the connected cog in the wheel, the tougher it will be to make the decision to let you or your team go. You are able to insulate yourself to some extent.

The changing face of enablement

As enablement evolves, more practitioners understand its value. The value propositions that have articulated what the role is, those success stories are being shared more than ever. Here’s how it has changed:


There's substantial content about our niche, the market, and what we do. While I've been in enablement for a while, the number of opportunities to speak about enablement today is far greater than say five years ago because there's considerably more awareness. 

Leaders understand the benefits of enablement, talk about it in their earnings reports, and put it out there for people to realize the outcomes and advantages.

Tech stack and data

The tools available have gotten better at giving insights. People are more willing to provide you with access to other systems and data. While correlation doesn't always mean causation, people understand correlating dashboards. They know enough to say, “Something is not working. Let's talk about it.” 

Client success

What do you do when you have to close every deal? You sank six months ago if closing deals is your maniacal focus at the end of every month or year. You've waited too long. The focus has shifted from new logo sales to the injection of client success and looking at revenue across the board. It's about situational revenue enablement of the new logo playbook. What are your playbooks for upselling, expanding, or renewing? 

Most companies will be lax about backing off an aggressive growth target in today’s economy. But they want to keep every dollar they earn. Here’s how enablement can help:

  1. Focus on implementation and delivery metrics, not new logo metrics. Instead of saying the sales process is 3% quicker, see is the implementation process now 3% quicker? Can you improve revenue by helping your company deliver more? Can you make the implementation team more productive? 
  2. Focus more on renewals with customer success managers. Do a timely business review, find a reason to reach out, and tell them about their adoption and attainment.

If you do this more, you are likely to get more returns. If you can get an early renewal, here are the incentives. If enablement is thinking of revenue, they need to understand where else and how else the company makes money. Try and attach yourself there. If a different department can borrow you or a teammate, then a year from now, they will be retained and able to return because the focus shifts back to new logo acquisition now. 

Coaching for success

Don’t bog reps down with mandatory coaching or videos because everyone has the same constraints. Instead, cross-collaborate with marketing, pool your resources, and interview all the SMEs for the SKUs you sell. While you want to sell a full suite, the budgets or buyer awareness won't always align. 

Go back to basics and break down your product into the various SKUs that match the solution set or the buyer's desired outcome. Instead of the full-suite solution, revamp your playbooks to their components. Use SMEs to create the training, explain how this works, why it matters, and who the target audience is. Implement a deal coaching exercise.

  1. What is the deal your reps need to close?  Look at account planning and opportunity coaching to determine what your reps are chasing. 
  2. Give managers a tool without asking them to be at eight different meetings about it. 
  3. Make a robust change management plan. Send it out to them two days before the reps.  

They’ll have the same list of deal coaching questions. When having pipeline conversations with reps, if these are the two deals they must close, here's this exercise to run through so it goes well. 

Focus on what matters: expanding, upselling, or new logos. Enablement needs to provide an opportunity for coaching assets to walk through because if reps lose, they must lose fast and move on to the next one.

Retain and expand

Don’t hold on too tightly to fancy sales dashboards. Shift your focus to client success when looking at dashboards and numbers. Who's coming up for renewal, and what can you add to that renewal episode? If they've products A and B but not C, D, or E, which is the best to fit to augment their solution set to give them a greater return? What can you do so your clients want to invest with you and keep the relationship going?

Spend most of your resources and bandwidth on the current customer base and try to expand and retain. The current economy doesn’t allow honing in on increasing average deal size and rising sales velocity. You'd be treading water and slowly drowning.

While getting new logos is enticing, increasing the bottom line is excellent, regardless of how you do it. Dig into where are you doing business today and where can you get a little bit more to get you through to the next year.

Your existing customers are also your references and can help you get more business over time.

Sales coaching and deal coaching

We operated a little differently earlier. Typically, the entire coaching exercise was structured, and playbooks had multiple practice components and applications. This ranged from practicing the elevator pitch, the first call deck, getting certified, etc.

The first call deck also played a role in listening for discovery questions, layering questions, and reps working their way through some anticipated objections based on the vertical or industry.

With the current economy and updated playbooks, we do deal coaching first. We debrief the deal by asking the right questions:

  1. Who will you talk to? 
  2. What do they care about? 
  3. Who is their boss?
  4. Who connects the dots for me? 
  5. Is there a customer story you're going to tell? 
  6. What's the ROI of that customer story?

We take our reps first through everything we expect to hear. As for pitch practice, we make reps self-assess where they need to improve, leaving it to the managers who know their teams the best. If reps are good at ‘A’ but wavered in ‘X,’ practice ‘X.’ Build the process strategically to be more open, not necessarily self-paced, but more reflective, allowing reps to know themselves. 

Where do you need to improve? Let's up-level you.” That's what you need to practice. The scorecard is generic but includes foundational components such as call-to-action, mentioning customer success, and checking for understanding. Self-assessment is critical when reps are hyper-focused on a small book of business – renewals and closing those deals to hit their number. 

Reps know where they need help, even if they don't want to tell you. So, don’t enforce completion.

Focusing only on completion takes everyone involved back to high school. As enablers, give reps the space to improve while they retain their autonomy. You were hired as an enabler, not a babysitter. If someone chooses not to follow your advice, that's a different conversation. Our job in enablement is to say, “This is the information we have in front of us, and we know from our leadership where we want to go. They have signed off on our plan to get there.” 

As for participation, when people start seeing results, others follow suit. Reps know themselves, especially those that have been selling for a long time, and sometimes, asking them the right questions has a significant effect. They'll mull it or think about it in their call planning. Even if they didn't record it for you to see, score, and give feedback, you still need to do the right thing in helping them get better.

If they're taking that to heart, putting it in their account planning, and it's working, you can look at other metrics – the opportunities booked, the dollar amount, etc., are more insightful than completion numbers.

You’re the product

I often mentor people looking to make career changes. Some of them want to be BDRs in the tech space. “What does it mean to be a good BDR?” They rattled off behaviors you would expect to hear, including competence, reaching out, persistence, etc. 

My advice to them is, “You're the product. You're selling yourself. It's a job and the meeting you've been trained to book; that's the interview.” Why aren't you doing the BDR job at the companies where you want to work? Be hyper-focused on reaching out to the team members and connecting the dots. Provide the value proposition of what you’ll bring to the table.

The same goes for enablement practitioners. When rolling out your engagement tool or new marketing communications, personalize it. If you have an existing program, provide coaching materials, and give VPs the personality profiles for coaching conversations. This encourages personalization within your programs. Successful training programs are personalized to the role and the individual. 

Find the right enablement role

For the best chance at success, being in the right role with the right people is important. Assuming you are walking into an interview for an enablement role, here are some things to consider:

1. Look for the background and expertise of the leaders you’ll be interfacing with, such as the C-suite or the executive team. If they're experts in your job, run. 

Are you being set up as an expert in your domain? Do you have the autonomy and trust to complete that part of the solution? Will you be trusted as the face of enablement at your firm?

2. Are they clear on the problem they're solving? Have they set themselves up to solve that problem for customers? Do they have KPIs? Are they investing in the solution? 

Enablement might be a part of that solution.

Enablement will work only if there is a product to sell. Based on where they are on that journey, you can discuss different flavors of enablement. If customers are unsure of the value proposition, enablement will become a training/onboarding function.

Invest in yourself

Knowing any domain like the back of your hand is hard work. Often, we don't give ourselves time for this self-growth. A common belief is that this is much more time and effort than most people give their job.

You need to remember that jobs come and go. What you invest in yourself, you take with you. When reps see it starting to work, they're more inclined to sign up for the next training. But most reps don't think about that. Remember, you're not investing in the company; you’re investing in yourself.

So, don't give it to your job. Give it to yourself. Learn everything you can about it. Identify your gaps through introspection, come to enablement, and say, “This is where I'm struggling. I need help.”

That's where it often gets lost. Enablement needs to make space for that using different tools. Start with reps taking self-assessments. These questions ultimately tell them their strengths and weaknesses. Sometimes, reps are self-aware and realize the reports are accurate. There’ll also be reps who have never done this before and are unaware. 

Once there is awareness of strengths and weaknesses, applying that information is a game-changer. Knowing how to interact with others on your team so we can all get to the finish line together is smart work. Enablement needs to work towards building that rapport, helping reps understand themselves better and know where they want to go from here.  

Times are tough. I think everybody should just really try and up their knowledge of the situation. If cuts are going to happen, you just want to make sure that you have positioned yourself well enough to insulate yourself from the turbulence ahead.

Feel free to tune in to this interview on Spotify or Apple Podcasts. If you prefer other platforms, simply click here to explore more options. Happy listening!

About the author


Ashley Philipps

Ashley Philipps is VP of Commercial Effectiveness at EverView (formerly Output Services Group).

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