Stephanie Middaugh
Table of Contents

Stephanie Middaugh is an industry veteran who wears multiple hats with equal panache. She is the Co-founder of ’The Enablement Squad’, an online community for enablement professionals, the Founder and CEO of Phoenix GTM Consulting, and the new Head of Enablement at Pinecone

In her interview, Stephanie talks about the challenges facing sales enablement today and best practices that can assist enablers in creating impact, even in the face of economic challenges.

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

Elevating the role of enablement 

The struggle enablement faces is that, most often, it’s relegated to a support function. While enablers love to help people, we get sales leaders and reps saying, “We need to do X.” Then we've got leadership coming from the other direction, saying, “No, ignore that.” Consequently, we fail to get buy-in due to misalignment with the leadership.

How do you elevate enablement to get closer to the how, when, where, and by whom the decisions are made? Enablement cannot just be about, “I had 20 people to train, and they got 90% on their LMS scores.” While that's fantastic, the CRO, CEO, or higher-level executive leadership will want to focus on business outcomes, such as

  • How did you impact sales velocity across the pipeline?
  • Did you improve the win rates? 
  • Are you getting more qualified leads?

The ideal state for enablement is to get as close as possible to the decisions being made in the organization and those making them. Else, you will be stuck playing a ‘game of telephone.’

Ensure the programs and initiatives you initiate are tied to a business objective. Also, make sure you've hard-hitting data because that's what executives care about more than anything else. That's where enablement can start elevating. 

Get product marketing on your side

Product marketing and enablement need to have a collaborative relationship.

Historically, product marketing and enablement have a significant overlap. Usually, product marketing is brought in first, and then enablement. Product marketing must also do a bit of sales enablement before enablement comes in. 

Product marketers may feel like their toes are getting stepped on when enablement is brought in. If you've got a CMO and a CRO reporting separately to the C-suite or executive leadership, they occasionally have different priorities. 

Civil War!

Another aspect to consider is the maturity of operations and their framework. For instance, when marketing and enablement run parallelly, a lack of overlap leads to frustration and a game of finger-pointing.

While clichéd, communication works best in these situations. Usually, there's miscommunication because product marketing and enablement are trying to do the same thing but get different goals or projects. It can be a challenging relationship, but we need to look to the senior leadership, come together, figure out the direction, and row together. 

Think beyond onboarding

It’s a disservice if organizations are pigeonholing enablement into onboarding new reps. While it is a crucial function, enablers are not just trainers or onboarders. Usually, onboarding is the first focus for organizations; however, your sales reps need to be as productive as possible.

All the elements that go into onboarding need to be continually reinforced with your sales team. Are they running the correct sales process? Are they using the tools effectively? Do they have the skills required? Enablers frequently have to break bad habits and create new, better ones based on what we need the reps to do. 

If and when onboarding stalls, take your current onboarding program and shift the focus to existing team members. It's a misconception that enablement has to do something completely different if we're not focusing on onboarding.

Be creative with enablement

At an enablement hackathon last year, a young enablement professional asked me, “How do I make my reps take my training?You can't, I'm sorry. 

You can lead a horse to water, but you can't make it drink. A 100% completion rate is a miracle. I aim for 80% completion because there will always be grumpy sales reps who know it all. Maybe you can't teach them anything. 

Ask them to teach you something instead, and you can train the other reps on how to do it. 

Be creative. For example, in my last organization, we took over the weekly sales meetings and used them to deliver bite-sized learning that was immediately actionable to the teams. We got phenomenal feedback from those sessions. 

This is an excellent example of what enablement needs to do. Meet the reps where they are and identify the target audience. Is it the folks who want to sit for an hour for a lecture? Is it the less experienced reps who want bite-sized learning? You don’t have to reinvent the wheel for every element.

Do a training on Zoom for the people who want to listen if that’s their preferred learning style. Record it, get it auto-transcribed, download it, and put it up on your LMS platform for people who prefer self-paced learning. Take small snippets of it and break it down. Microlearning is the way to go. Instead of thinking outside the box, break the box.

Enablement 2.0

Suppose a rep is six months into the job and is talking to a prospect from a healthcare company for the first time. What questions should they ask on a discovery call with this prospect right now?

Where does the relevant information live? How do reps accurately get what they need now, those critical pieces of information they can put into practice immediately from enablement?

Some old-school leaders say they don't want to serve information on a silver platter for their reps. “We hire professionals, tenure people, and pay them a lot. They should be able to figure this out and piece things together.” 

Amidst everything that sales reps manage daily, it's not fair to expect this from them. What's wrong with us serving information on a silver platter? If we can make the information more easily actionable, why are we forcing them to join the dots? What if they put it together differently or assume things incorrectly? 

Your sales leaders now!

Another element we need to focus on is training sales reps to think critically. That's the piece that often misses that mark. Supposing we give sales reps the tools and relevant information. Let’s then turn it into a teach-someone-to-fish situation. What if we taught sales reps to leverage it and apply it to their system and process instead of trying to conform to a specific process they need to follow?

Find that middle ground between you and your reps. Instead of hour-long seminars and lectures, find out what reps need to know now. That is where the gold is.

Enablers are sellers too (in a way)

My way into sales enablement was from sales operations. It just dawned on me recently how enablement runs the sales cycles internally with stakeholders. 

Enablers must manage stakeholders, prioritize and tie objectives with their initiatives to get approval. We need to make a comprehensive discovery. Is the priority qualified? Do we have the budget? Do we have someone who can champion us? We need buy-in from different stakeholders across the business. Once we ‘close the deal’, we must deliver, evaluate, and ensure customer satisfaction. 

That is our value proposition and how we do it.

I am a big fan of starting in enablement by coming in and having multiple conversations across the organization. I always ask for a few things whenever I join a new company. I want meetings with executive leadership (if I can get them), frontline managers, and sales reps. Usually, they give me meetings with the sales reps or put me in contact with sales reps who tell me that everything is sunshine and roses.

Everything is perfect!

I want to find out their roadblocks. What's happening? Where's the dirt underneath the rug? I need to come in and see all the skeletons in the closet. That's what I need to fix. 

Don't be afraid to come in and look for the bones or the ghosts in the closet. Seek those out and quickly identify what you can fix with the least lift. Then focus on what are some of the long-term projects. Go to leadership and say, “These are the things I've identified. I want you to tell me what the priorities are in your mind.” Because if enablement identifies the priorities, you run the risk of leadership disagreeing with you. Put the ball in their court and work together to come up with the right course of action.

That's what you want to look for in an organization because somebody is hiding the dirt somewhere. You could either step in it or clean it up.

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


Stephanie Middaugh

Stephanie Middaugh is the co-founder of the Sales Enablement Squad and the new Head of Enablement at Pinecone.

Subscribe to Elevate,
our bi-weekly newsletter.

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