Don’t Be a Yes Person – Ask “Why” To Qualify Leads

Danny Wasserman: This is Reveal: The Revenue Intelligence Podcast, here to help go-to-market leaders do one thing: stop guessing. If you’re ready to unlock reality and reach your full potential, this show is for you. I’m Danny Wasserman coming to you from the Gong studios. Howdy, howdy, howdy! Danny Wasserman coming to you for another weekly episode of Reveal. Yes, of course. In the house today, we have someone self-proclaimed to be a razzle-dazzle revenue leader. And I can think of no truer description of this individual’s energy.

Yes, we can think of her as the head of enablement at Dandy, but my goodness, she is bringing the thunder. She is bringing the heat, all the pizazz and panache any enablement organization, or for that matter, go-to-market team could ask for. We’ve got Devon McDermott in the house. And as a fellow enablement leader, it was awesome to hear some of the things she’s constantly thinking about to drive success within the Dandy ranks.

First and foremost, making sure that she’s serving from the back, making sure that she’s prioritizing, giving those tenured, seasoned, absolutely killer sellers all the time, all of the chances, all of the opportunities to be front and center, and she’s just supporting them from the back. Love that philosophy. Another thing, when it’s so tempting to get whipsawed by the shifting tectonic pivots of selling in today’s market, what I like so much about Devon is that she is not defaulting to saying “yes” to whatever those evolving demands are from the go-to-market constituency she serves. She’s in the practice of always asking, “Why are we shifting gears? Why are we pivoting strategies?”

And I think that is a healthy reminder for all of us, whether we’re enablement, or in fact, whether we’re leading our own frontline teams. Those could be sales or CS. You don’t want to hear from me; you want to hear from Devon herself. So, let’s get straight to the razzle-dazzle revenue enablement leader, Devon McDermott. DJ, spin that.

Devon McDermott: Danny, thank you so much for having me. I’m so pumped to be here, and I’m going to nerd out a little bit.

Danny Wasserman: Yeah.

Devon McDermott: It’s pretty wild to be chatting with you because anytime I’m on a podcast or panel, I find myself nerding out very hard about Gong because I’m obsessed with it. So yeah, I’m so pumped. Thank you for having me.

Danny Wasserman: I think this is just going to be a gush fest. We can fanboy and fangirl, and fawn over each other in this love fest. It’s going to be awesome.

Devon McDermott: It’s a beautiful thing.

Danny Wasserman: All right, so I’m doing research on you in preparation for the episode, Devon. And what I like so much about your tact is that you think about, “Okay, what are the various transitions in this profession in the 10 years or so that you’ve been doing it?” There was a period where there was sales enablement, and now we are in this paradigm of revenue enablement. Help us in the studio, help our listeners understand and appreciate, why is that distinction so important?

Devon McDermott: It’s so important, and it’s just incredibly interesting. So, sales enablement was kind of the pioneer. Any enablement practitioners that you’ve met got their start in sales enablement. But today, the shift is really moving where companies have seen the impact and power of a sales enablement function in supporting revenue growth, supporting effectiveness and efficiencies. And they kind of want enablement for all of their teams.

So, this shift from sales to revenue enablement is fundamentally about expanding and refining our enablement programs to encompass pretty much all of those customer-facing roles in an organization. Particularly teams like customer success and support, empowering all customer-facing teams, not just sales. And ensuring that enablement programs and partnerships are designed to meet each of those team’s unique operating structures, expectations, and goals. And most importantly, I think that the why for this shift to revenue enablement is to nurture a more consistent customer journey, which is what it’s all about.

Danny Wasserman: Well, we’re now living in the golden age of revenue enablement, but it wasn’t always the case that we had a seat at the table. You described this era of sales enablement and it being really siloed to that group within go-to-market. Even our entire notion of go-to-market was in its infancy back then. So, walk us through the good, the bad, the ugly of those early years of it just being kind of restricted or marginalized to sales enablement. I want to start from that gloomy moment when we didn’t have a legitimate voice, and then how that looks and feels different in 2023.

Devon McDermott: Yeah. So, it’s all about consistency in the way you show up for your customers and the way you communicate about your brand. And so again, we spent this time, energy, and money making sure our sales team was showing up like amazing partners. They understood the industry, they could speak effectively, they could support our customers in such an amazing way. And then those customers would move over to customer success, and you have a completely different experience. Sometimes a different message about the business, the value prop, what you actually do.

And so, you kind of break that customer journey as soon as they move on to the next team in your organization because there isn’t that thread. You’re not threading that consistent approach, messaging, methodology, way of engaging your customers about your business. And as a customer, that stinks, right? As an enabler, I purchased a ton of technology, I go through tons of sales cycles, and there’s nothing worse than having an amazing experience with your seller and then showing up for implementation and being like, “Who are you people? What do you do? What did I buy?” We’re doing that to our customers for the teams and companies that we support because we’re putting all of this effort and energy into making this stellar world-class sales organization and kind of dropping the ball for the rest of our team.

So, I think a lot of organizations started to see that, and maybe not necessarily the negative side of things, but the positive side of sales enablement impact. So, you have these onboarding programs, these ever-boarding programs, upskilling certifications, all of these things that are actually working. You’re creating a unified force. Your team is on message, you’re executing flawlessly. So many organizations said, “Wait a second, I want that for my customer success team. I want that for my marketing. I want that for all of my teams.”

A lot of businesses organically just started stamping out enablement across their other teams. And frankly, that is what happened to me. That’s how I fell into revenue enablement. When I was at a company called Sailthru, I started in sales enablement. Thankfully they hired me. I had not been a seller before, and I had literally no idea what I was doing. I barely knew what enablement was, and they just took a chance on an unknown kid, and I was able to partner with an amazing, honestly the best sales leadership team I’ve ever worked with in my career who took me under their wing, nurtured me, but helped me figure out like, “Hey, how do we shape a sales process? How do we build a methodology?”

And we were able to really build out this very hearty, very impactful sales enablement program. Again, all the things we just mentioned: you had our kickoff certifications. And my head of customer success was like, “This is cool. Can we do that for CS? But maybe just some webinars.”

And that’s how we fell into it. So, I didn’t have a strategy or an approach, and I did do what you’re not supposed to do at that time, which is rinse and repeat. Initially, I was just like, “Hey CS, come join our sales enablement webinar so at least y’all are hearing the same things and thinking the same way,” which did incrementally improve those customer conversations. But we really had to take a look and see, how do we modify this programming for this unique group?

And then eventually, we expanded our scope to customer enablement, which was really cool. So many organizations, customer enablement sits in your L&D team on customer success, but bringing that group into enablement was so incredible. Now we have full command of the message and full command of that customer experience. And wow, so much magic happens there. I think I’ve gotten a little bit smarter in my strategy when it comes to revenue enablement, but it was a really cool, exciting kind of just throw your feet in. What is it? Jump into the deep end of the pool and figure it out.

Danny Wasserman: Love it. So, you capture lightning in a bottle with this sales team, and people are like, “Holy smokes, what the hell is Devon cooking up?” It’s contagious. And then other people are saying, “Well, whatever she’s doing, I want it for CS.” You talk about perhaps unfortunately early on making that mistake of a one-size-fits-all approach. But stick with me to the question, which is, okay, it’s hard to quantify what enablement does. Speaking as an enabler, I feel that all the time. You’ve created magic in sales, but people are having a hard time abstracting or extrapolating your value. They just know they like it. So, when you say, “Well, I can’t do this for sales and for CS, I need someone who specializes in CS enablement,” and that’s another headcount, and you’re already a cost center. How do you go to the CFO when times are tight, even when times are good, and justify the headcount? What’s your justification?

Devon McDermott: That is a challenging one. Thankfully, a lot of that has happened organically, but I think we can start to show the impact of the work that we’re doing, which I will caveat, this is the hot topic in enablement: demonstrating your impact. It can be really hard to do if you’re a sales enablement team of one and you’re in a startup. So, we know at a startup—and I’ll use that as our example to kind of frame up the conversation—metrics might not be defined. They might be tracking them in different ways. That might change day over day.

So, for an enabler who is trying to expand their team and bring in a full revenue enablement function, you have to find the areas where you can actually track the impact of the work you’re doing. And so for the sales team, what we were able to do is look at, how are we shifting the behavior of our reps? A simple example: we have a new pitch, and we need to get everybody on message. How do we do that? Well, we can demonstrate through our enablement programming, through training reinforcement, role-playing—I love a certification—through certifications, we are getting our new reps comfortable with this new messaging. But how do we know it’s working?

We’ll use our tech stack. So, using things like call recording, Gong, and your CMS, we can start to track, are people able to do this thing that we expect them to do? If they’re not, what can enablement do to actually help support that behavior change? We’ll set up scorecards for our managers and get them involved for reinforcement. So now we have this super holistic program. We’re tracking incremental moments: yes, enablement is delivering all this great stuff. Good for us. Yes, people are taking our programs. Great, even better. And hey, they’re actually using this on calls with customers. And hey, those calls are actually resulting in better conversion rates, more robust discovery, better demos. We can actually show that.

Now, the direct impact on revenue is a whole other story, but we can start to draw those correlations and tell the story of the impact of the work we’re doing. So, having that business case or case study to share back with your CFO shows, “Hey, if we just threw the talk track at our reps, some of them would adopt it, but we’d also be working with nebulous data and insights to say we think they’re adopting it, we think they’re following what they’re supposed to be doing, but we don’t really know.”

And so for enablement, it’s methodical tracking of everything you’re doing and being able to report back on whatever you can. Now, I just made some big statements about your tech stack, call recording, and CMS. I also know a lot of enablers, especially if your CFO says, “We’re not spending money,” don’t have any of that. And so it’s figuring out ways, if you don’t have access to the tech, to track that. You can still build a business case back to the CFO, but it has to be data-driven, and you have to demonstrate that the work your team is doing is moving the needle.

Handling Resistance from Tenured Sellers

Danny Wasserman: Let’s talk about the use of data to legitimize everything you’re doing, and presuming you have all of the elements in the tech stack that you just enumerated. Awesome. Let’s talk about a really commonplace scenario where you’re either in an organization or you join an organization, and you’ve got that really tenured enterprise seller. They’ve been successful long before you arrived at the org, maybe long before you were born. And they say, “Get out of my way. Get this monkey off my back. I know what I’m doing.” How do you contend with reluctance, resistance, stubborn behavior that flies in the face or defies what it is that you’re espousing?

Devon McDermott: Yeah. I’ve worked with so many of those reps. Some of them are now my very good friends. Especially for me, with no sales background, already the target is, “You’ve never carried a bag. How dare you tell me how to run discovery? Who are you?” So I’ll take a step back. What do I have control over? I’m going to read every book I can. I’m going to follow every sales leader, CRO influencer on LinkedIn, and learn everything about them.

I’m a very shy, strange introvert. It may not seem that way, but I’ve actually called people and said, “Can I have a call with you? Can I unpack your brain?” Now, those aren’t the reps we’re talking about, but I want to make sure I’m backing myself up with a little credibility, knowledge, and to show my reps that I’m doing the work. But for that rep who’s been selling for longer than I’ve existed, I make them my partner. I say, “You are my new best friend. You are my SME. You are my partner. Let’s run a discovery session. Come build it with me.” If they’re too busy, I’ll build the whole thing for them and ask for feedback.

Help me run those Gong call reviews, help me make sure our reps are on track, be the face of the programs that you are the star of. Really celebrate those folks, evangelize them, bring them into the fold. In enablement, we talk a lot about change management, and we know a lot of that is heavily dependent on your guiding coalition, getting the buy-in, building the groundswell, building your evangelists. That super seasoned rep is your number one evangelist. You bring them in, ask for their feedback on things, make them the star of the work you’re doing.

I can’t tell you how many workshops and training programs I’ve built from my enablement layer and then said, “Here you go, go be the star. I’m the stage mom in the background.” And that’s okay because I know that’s what’s going to make it work. So it’s psychological where A) I need to show up as a trusted partner to you, and B) I also need to say, “Danny, you’ve been doing this for 25 years. Teach me the way. Let’s do some knowledge sharing. Let’s grow together.”

Danny Wasserman: I think that it’s the humility with which you’re approaching this, which avoids the all too common dynamic of finger-pointing. “Why don’t these lazy people do what I’m asking them to do?” And sellers looking at us and saying, “You tone-deaf, ivory tower, Evian-drinking doofuses.” So I love your tactic when it comes to being a partner, saying “This is not our show to steal,” and propping them up. It’s awesome.

Devon McDermott: Yeah. And I think too, being crystal clear that everything enablement is doing is in service to sales. We don’t have our own agenda. There’s often a disconnect because enablers are fighting for a seat at the table to be C-level, to be strategic, to have a voice. We need that, but we often lean on that to say, “Well, the CRO said we have to do this training on X.” Then we go build it, and we don’t have sales leadership buy-in. Our reps say, “What are you talking about? We’re doing fine on mutual action planning.”

It’s also about finding our job as the dot connector, as the cross-functional person who’s saying, “Hey, CEO or CRO, we might need some work on that mutual action plan. Tell me why.” Then you go back and scope it, and say, “Great. I’ll make sure the sales leadership team is fully bought in.” I’ll go back to the reps and run a field advisory board, run voice-of-the-field programs to figure out where challenges are. You must ensure that any time spent asking your team to step away from revenue-generating activities is actually time well spent.

The CRO might’ve heard a soundbite in a meeting and said, “Everything sucks. No one’s doing what we need them to do.” Enablement must take a breath and say, “Great, let me ask you some questions and I’ll get back to you.” Use the data that’s available to you, talk to your teams and leadership, and build a plan that works.

Danny Wasserman: The art of enablement is rooted in fostering relationships between sales and the rest of the cross-functional teams that have a vested interest in sales adopting their agendas. In healthy internal relationships, those lead to clear and consistent customer outcomes. According to Gartner, by 2025, 89% of customer interactions will be managed by AI, through chatbots and messaging apps, which will help us but cannot replace the human-to-human component.

Let’s get back to Devon and hear more about asking those why questions to deepen partnerships. Devon, you said you slow down and connect the dots, which implies that there’s pacing and composure in the role. Walk us through how to reasonably course correct with the volatility that comes with the role of connecting the dots.

Devon McDermott: I like to joke that I always have a contingency plan in place. I blueprint the heck out of every program I build. I have a map that allows me to pivot forwards or backwards. Explosion and everything’s falling apart? We pivot with a contingency plan. It comes down to thoughtful change management and methodically aligning with where we need to go. We must also get the right people in the room, reset the vision, and determine our path forward, using all the data available to make good decisions.

When we react without consulting cross-functional teams, we miss the forest for the trees. I always ask, “Why is this a problem now? What did we miss?” For example, urgent changes from a new competitor may prompt a pivot, but we need to ask the right questions. Instead of a full certification program, we might need to focus on getting the right information out first, and then focus on behavior change later.

I think my biggest pet peeve in enablement, especially because we’re constantly trying to show leadership our value, is that we don’t slow down enough to ask the right questions. I ask, “Why? What data do we have?” It only takes a moment, but it ensures we’re solving the right problem.

Danny Wasserman: You talked about correlation and causation, and how you can’t always causally say enablement hit a number, but you can show how it contributed. How do you wrap up the year and say, “Our team kicked ass and here’s what we delivered”?

Devon McDermott: We track behaviors, like new messaging adoption using Gong and CMS tools to track how reps are using what they’ve learned. Monthly roll-up reports help show leadership what we’ve delivered and its impact. We track quiz scores, certifications, and behavior changes in Gong, and use the data to show that reps are engaging in the right behaviors that lead to better business outcomes. If better pitching or mutual action planning isn’t working, that’s something we need to track and address too.

In my current organization, we track the resources delivered, such as reinforcement moments, job aids, and scenarios. We also track whether teams are engaging with that content. And for those using tech like Gong, we can track how they perform on calls, their progress, and improvements over time. It’s not perfect, but it helps tell the story.

Danny Wasserman: Looking at the clock, we ask all our guests the same question. I’m curious: if you could describe sales in just one word, what would it be?

Devon McDermott: Juggler. Sales is like juggling multiple tasks—prospecting, relationship building, negotiating—without dropping any of the balls.

Danny Wasserman: And if you could describe enablement in one word?

Devon McDermott: The great unifier. Enablement brings together all the strategies and people needed to succeed.

Danny Wasserman: Devon, it’s been an absolute pleasure having you on the show. Thank you for all your insights and for setting an amazing example in the enablement space.

Devon McDermott: Thank you, Danny. It’s been awesome chatting with you.

Danny Wasserman: Thanks for listening to this episode of Reveal. For more resources on how revenue intelligence can help you create high-performing sales teams, head over to Gong.io. And if you enjoyed this episode, give us a five-star review on Apple Podcasts, Spotify, or wherever you listen.