Gap Selling Expert's Secrets to Sales and Marketing ft. Rachel Mae

# Revenue Reimagine Podcast Transcript

And so I started teaching my sales team Gap selling, and within six months, the whole world changed.

Welcome back to another episode of the Revenue Reimagine podcast. We are so excited to have with us Rachel May, who is the GM of Partnership Enablement at a Sales Growth Company. She's also a multi-time former head of sales and an expert on all things Gap selling, which we'll talk about in a little bit. Rachel, welcome to the show.

Thank you, I'm so excited to be here. That was such a nice intro. I try, and it's like one of the few books back here that I've actually read. It does sit right here. Everyone sees it, and every call that I'm on, we'll talk about why Gap selling works. Um, why that's one of the few books I read. But let Dale ask a question.

I wonder why it's only one of the few books you read, but we'll get into that later. I just learned how to read, dude.

Rachel, thanks so much for joining. So you've been in sales for a long time. You talk to a lot of sales and marketing leaders. It seems like alignment in revenue has become so difficult nowadays. Talk to us a little bit about the most creative way that you've gotten to align a sales and marketing leader and how that alignment actually came to be valuable for them.

Wow, coming straight out the gate, Dale. I got to solve sales and marketing alignment, really. This is as old as time, right? You know, I think what I focus on is aligning the entire revenue engine in marketing, you know, in sales and CS around a shared common sense of values and a common idea around how we think about our buyer and how we speak about our buyer internally and externally. And so what we really focus on is: What are the problems, the business problems that our products and services solve for these buyers? And getting really specific and clear on that. What are the root causes? What are the impacts? And if we can align the way we all think about our buyer and the way we all speak about our buyer to our buyer, then we're all on the same mission.

I love that. I wonder if alignment can even truly happen or if people are just giving up on it. What do you think about that? Have they given up on it?

No, I don't think they've given up on it. But I do think that part of it comes down to a huge lack of understanding around who owns what, right? Is it getting too blurry?

I definitely think it's getting too blurry. I think it's always been too blurry. Who owns what? Interesting, right? So I agree with you. I think it is blurry. But I also think that alignment is a term that people throw around, like, "Oh, let's all get on the same page and let's have alignment." When most people don't have the ability to align because, and this is just my opinion and I'm super curious your thoughts, you can't align if you're incentivized on different things. When marketing is incentivized on leads and sales is incentivized on sales and CS is incentivized on God knows what, and everyone's not incentivized on revenue as a whole, how do you get aligned? Marketing says, "I'm giving you great leads, but your sales folks suck." Sales is like, "We could close everything, but your leads suck." Marketing's like, "But you just don't know how to sell. Maybe you should go read Gap selling."

How do you fix that again?

I think that comes down to ownership. Does marketing own that revenue piece, or do they just own delivering leads and that is what they're measured on and that is what they're held accountable to? That might change from organization to organization, but as long as you have clarity and agreement on who owns what, you're going to bring down some of that conflict. But to your point, Adam, I don't think that alignment means agreement always.

Right, like tell me more, right? Like to me, I need the customer journey to be aligned. I need everything external to be aligned. I need the messaging to be aligned all the way through that buying cycle. But that friction between marketing and sales is not necessarily a bad thing, right? When marketing is pushing on me and they're like, "Hey, what is happening with these leads? We are delivering these leads to you. Please help me understand what the process is and how many meetings are getting booked and if they're getting converted, and if they're not getting converted, we need to all get some agreement on: Is it because I'm giving you something and asking you to turn it into gold, or am I giving you gold and you're letting it sit there and not turn it into whatever gold is supposed to turn into?"

I love that, right? Like I love that conversation about it being about the customer journey and alignment on that customer journey. And then it always—I always wonder, is it a compensation issue internally? Because if they're getting comped on leads, they're going to give you leads. If they're getting comped on leads that turn into opportunities, then that may be a whole different conversation.

Yes, yes. I'm—oh, go ahead, Adam.

No, please, Dale, go ahead. I insist.

Well, I was super curious because you're a sales leader and you've been a sales leader in many different places. What other parts of the organization, the go-to-market function, would you take other than sales? What would be your go-to if you couldn't be a sales leader?

Going right for the normal rapid fire end, you know, these days I would say if I couldn't be a sales leader, I would go be an Enterprise rep. Why? Because I love selling. I love the strategy that is involved in Enterprise. It's like a giant chess game and you're playing the long game. And it keeps me, like, it's very compelling to me—that Enterprise sales cycle, the strategic, the maniacal, operational part of it, all the moving pieces. And yeah, so that's what I would choose. I think that's the best job in sales.

So that's interesting. I want to come back to that, but you said something that hit home with me. You said you love the strategy of Enterprise sales, that it's a chess game. One of the things that we talk a lot about with revenue leaders and with founders is go-to-market strategies that just aren't taught enough, aren't used enough. And oftentimes they're the lesser-known things that really can make a huge difference in whether your deal is going to close, everywhere from SMB all the way up to Enterprise and even SLED in government as well. Talk to me about one or two go-to-market strategies in your mind that aren't taught enough that you've seen, either firsthand or secondhand, make a huge difference in closing deals.

I mean, I can't not say Gap selling. I mean, you can if you give some context. I won't poo-poo it totally. I think the number one thing right now missing in people's GTM strategy is that there is not consensus around the product-market fit and who do we sell this to and what problems do we solve for each one of the personas? None of that is new, right? Like, that concept is not new. But it seems like every conversation I have today, there's something that was done in the beginning, it's done once, and it's not done again. It's not done consistently. And then we add a lot of features and we have acquisitions and we all of a sudden offer this full product line. But all of our PMF is focused around kind of that initial product. And so I see this big loss in product-market fit and in understanding who we now sell to that maybe we weren't selling to in the beginning, and then what problems do we solve for them. And I know it's like a horse that I keep beating, but it's what I see every day. Every day I meet with CEOs and VPs of sales and my first question is: Can you help me understand what business problems your product or services solves for XYZ that you just told me you sell to? And they struggle to answer the question.

True story on this—I post, because I ask every founder also: What is the number one problem your product solves for your prospects or customers in under thirty seconds? Don't give me a diet tribe. Don't give me a dissertation of you know, we do this, this, this, this, and this, and because of this. Quickly. You're in an elevator with someone who's like, "What do you do?" How do you answer that? You're spot-on, 100% correct. Or they'll give you what their product does, right? They'll tell you the technical jargon that goes along with it. And in larger organizations, you just multiply this by a hundred. I mean, this is hard enough when you're talking about a Series A company, right? But like, I just worked with a huge company with fifteen-hundred reps. They've had multiple acquisitions over the last five years. They're integrating AI. Their product has just changed dramatically. And they've done no work in understanding: Who do we sell to now? What problems do we solve for now? And I think people think this is like an isolated thing that you do when you're seed stage and you never do it again. But it changes. And it changes. You know, there are all these products and services that came out during COVID that...

We're solving a COVID-specific problem, and now that problem doesn't exist anymore. So they just keep adding features trying to make this thing relevant. But they don't know what they're solving. If we could fix that one problem in organizations—your go-to-market strategy—everything comes from there. Literally everything stems from there. But they're building playbooks and they're building processes and they're building marketing messaging and they've no idea what that foundation is.

And so then you mentioned something about AI in that conversation. Is AI helping us, or is AI hurting us? I think everyone's trying so fast to get the AI features out and the AI products in products and get all these integrations. But they're doing it again without a sense of: are we really solving a problem here, or are we creating shiny objects?

So in that sales process, we're not creating the right foundation. I think everything you were saying was let's build the foundational elements and then we can build on top of that. But people are trying to put the AI piece on top of already broken conversations, broken ICPs, broken buying personas. How do we stop? Because everyone wants it done now—more revenue today—what are three things you would recommend every founder do immediately? Like three things they can do today to help them stop, get off the hamster wheel of trying to fix something that's broken?

My number one recommendation in early stages is you're going to need outside help.

Oh, I like that.

But not any outside help, right? Because they probably get tons of information. Like, how do you articulate the right thing? How do you vet the right outside help? People buy from people. That's why companies who invest in meaningful connections win.

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And I would say, like, if I was a founder right now, the first thing that I would be doing is I would be finding a consultant who specializes in product-market fit. And I would be looking for someone who has a process that they follow to nail that down.

For example, and you could do this by yourself, but you're so close to your baby. You're so close to your own baby, and it's just you have blinders on. You only know your world, and you haven't seen this play out in multiple organizations across multiple worlds, right? And so your perspective is going to be very narrow, and you're not going to think of the things that someone else is going to think of from the outside when they see your problem. Because they're seeing it from a lack of industry knowledge. It requires curiosity that you don't have when it's your own baby, because you think you already know it.

So, for example, the process that we use is our problem identification chart creation. And one of the first things that we do with all of our clients is it usually takes like four, maybe five sessions to get their problem identification charts refined. And they might need one, or they might need multiple ones. It depends on if you're selling into wildly different verticals with wildly different personas that you're selling into, right? The business problems that are vested in might be wildly different. But for most organizations, they really just need one overarching one.

But how we do this is we get marketing in the room. We get product in the room. We get sales in the room. We get CS in the room. And we're going to get on calls and we're going to hash this out, right? And in a lot of ways, we're playing moderator there because nobody agrees. Nobody agrees what the problems, impacts, and root causes are that we're solving. In the same room, you're like, "What's the problem?" And everyone's got a different conversation. Everyone's got a different thing. Everyone's got a different perspective on it, right? Which is actually terrifying to me. It's terrifying when the CRO and the head of product have a completely different idea of what this thing is solving. What are you building over there? What is product doing, right?

So they're just building shiny objects. Sales is coming and going. "I met with this client, and XYZ competitor has this. This one client needs this. So drop everything and build it." They're chasing it, right?

Yeah, so that's why this exercise is so important. Because you're getting everyone there, and you're creating these problem identification charts. And then you're fighting about it. You're duking it out, man, until you have that agreement. Well, once you have that, whenever someone asks for an additional feature on the roadmap, you're okay, here's the problem identification chart. Tell me how it solves these problems. Or are we now chasing another problem? And if we are, where's the business case for chasing a new problem?

Identify the big. Identify the loud versus the important. You could have one customer or one prospect who's screaming that they want this one feature. But how much revenue is it going to drive? We used to do an exercise where every sales request would have to come with an ROI analysis. How many customers are going to buy this? What's it going to bring in? How quickly are they going to buy it? And prove it.

Yeah, I love it. Most of the time, that feature that the client is requesting is a shiny object. If sales understands the problem identification and how to do that with their clients, then not having the feature probably isn't going to stop you from getting the sale. It's something that someone told them that they had, and now they're like, "That sounds really nice. I would love to have that. It sounds fancy." But when you really dive into what the client is looking to solve for, nine out of ten times, that thing is just a nice to have. It's not actually going to solve their problem. It's a distraction, right?

But the salespeople don't know how to do that—how to ground the client in the problems they're actually looking to solve and help the client go, "Should I really be making this decision based on a feature that doesn't actually solve my problem?"

One hundred percent, right? And it cascades throughout the entire organization. If everyone could do this one thing—if we could do it as foundational in our organization to understand our product-market fit and shape our messaging around it—then now once we have those problem identification charts, sales knows exactly what to look for in discovery. I am looking for these five problems. I am looking for these root causes. I am looking for these impacts to measure. And if the client is asking me for something that doesn't help solve those things and that's what they need to solve, then I can counsel them in that way, right?

What's the gap? Um, all starts with problem identification.

So it's funny you said, "What's the gap?" That's exactly where I was going to go next. So there's a ton of sales methodologies out there, right? Rachel, there's GAP, there's Challenger, there's MEDDIC, there's SPIN, there's whatever the hell you want to call it.

Rachel says there's only one whole. Slow your roll.

Um, because I'm getting there. You're slow. You're a successful sales leader. You didn't have to go work for anything to do with gap selling. You could have gone to be another sales leader somewhere. You could have probably gone to work for Challenger or whoever. Like, why gap selling? What is it in that? And this isn't a pitch, but like, what is it that makes gap selling work? Because I am a huge fan. Like, I will say that. Gail, Gail, Gail Dale D Dale, just asked the right question: what's the gap? Talk to us a little bit about gap selling and how that comes into play with all of this.

Yeah, I don't know if you know this story, but okay, so I come from the copier world. So I worked at Xerox and Konica Minolta, and I was in learning and development there. So I was a sales trainer at Xerox much. What we were teaching was very Challenger-esque. And why Challenger-esque is I love Challenger, but it's not really a sales methodology to me. It's theories. It's principles. It's research, right? But there's it misses the execution piece, right? Like, okay, this all sounds really great. I understand why I should sell this way. But like, how the F do I do it, right?

So that's kind of how I walked away from that. And so we were like building kind of the dirty street execution arm of Challenger principles. And it was working with certain types of reps, and it was working in certain types of deals like enterprise deals. But it wasn't working in mid-market, SMB, and it certainly wasn't working with my twenty-four-year-old straight out of college with a business degree who didn't know their ass from their elbow, right? Like, it was not working with those people. And in fact, we were turning over almost one hundred percent of new hires year-over-year.

Wow.

Um, so I was poached to go over to Conforce, and I was over there kind of doing the same thing again. They were getting better, but my sales cycles weren't reducing. My average sales price wasn't going up. People were still discounting their faces off to get deals, and my ramp times were still at like six months to a year before I had a really productive rep.

# Transcript

Rep, which was a huge problem when my average tenure of a new rep was 12 to 18 months, right? Which you see a lot of this out here today in all industries. And I started following Kenan, and I was in my dream job, y'all. Like, my dream was to become a regional director of sales where my real job was to go around teaching people. And that's what I was doing. I had hit where I wanted to be in corporate America.

I started following Kenan, and then Gap Selling came out. I read that book, and I was like, "This is every single thing that I have been trying to teach." But the way that he positioned it and packaged it made it so executable. So I started teaching my sales teams Gap Selling, and within six months, the whole world changed. My reps were getting their first deal within like two months. My sales cycles were going down. My average sales price was going up. My productivity per rep was up like 36% after only four months. And I was like, "This is it. This is the Holy Grail."

So I actually messaged Kenan on LinkedIn and I said, "How do I become you? Like, I want to be the one who goes and does all the Gap Selling training. I want to be the one." And he said, "Well, you could do that someday. But right now you can come be my AE." So at 40 years old, I had climbed all the way up the ladder, and I freaking packed up and joined the circus and became Kenan's AE for like two years because I really wanted to master it.

And so I guess the long answer to your question is I've tried them all. I've done SPIN Selling, Solution Selling, Challenger Sales. I've done it all. I've taught most of them. And this was the only one I've ever found that works no matter what—whether you're small, mid, enterprise, whether you're a brand new rep, whether you've been doing it 30 years. It's relevant no matter where you are because it is based on how human beings decide to change. How humans change. What is the neuroscience behind what is the process that we use as humans to decide whether we are going to change from our current state to something else?

And that's the biggest problem. That's the biggest gap in all selling. How are we going to get you from doing what you do today to something else?

100%. That's all it is. Everything, everyone is selling change. And salespeople are change agents. Which means we need to be able to take other humans through their change management process.

And I love in the book like he says, "You don't know the game you're playing." And I think when I look out here and I see all the advice and I see what people are talking about, they don't know what they're up against, right? Humans are very change resistant. We do not like change. We do not want change. We will do anything to stay in our status quo state. That's why 70% of deals are lost to status quo.

So if you can't as a salesperson uncover if their current state is "I can't stay here anymore because the cost of staying here is too big. It is going to ruin me if I stay. My current state is intolerable or untenable." And what we're doing today is we're waiting for people who have already done that work themselves, diagnosed themselves correctly, not incorrectly, showed up on our doorstep and said, "I must change." When you have a 15% conversion rate, that's who you're getting.

And that's not sales. I'm sorry, it's not. It's order taking. You're getting lucky. If you want to get into 25%, 35%, 45% conversion rates, you've got to take the people who have not figured that out yet, who have misdiagnosed themselves, and you've got to move them from "I think I'm probably doing all right" to "Holy, I've got to change now."

And the reason I think Gap Selling works is because it bifurcates those two sales. So the first sale is "Yes, I must change." And the second sale is "Yes, I must change to you."

What most sales methodologies and processes and sales organizations are doing is they're saying, "Person shows up. Here's how you get them to 'I must change to you' when they have not even decided they must change yet."

See, Adam, you can change. I knew you could do it. You can do it. I can here. Here's the funny thing though. You said sales folks are change agents. Hey, Dale, before we partnered together, what was the name of your company? Because I saw your face. Sales Change Agent.

That was my. I love that. Yep. Yep. It was a great play.

Rachel, so we believe in giving back at Revenue Reimagined, and you've been super kind to give something to the audience. Let them know what you're going to give away.

Yes. So I'm going to give away five Gap Selling books today. Or if you already have a Gap Selling book, you can choose a t-shirt. I love that. Yeah, I have my book. My signed book. We're gonna have to get Rachel to sign the book for you to send it out here. If only Dale knew how to read and didn't listen on Audible.

Super pictures. We won't talk about the type of books you read on this show. We do have an explicit label on the show because we curse a lot. But we can't go there.

Rachel, before we wrap it up, let's throw some rapid fire out there. I think you dropped a ton of value, and we could go on forever. But this is only a 30-minute show because no one wants to listen to Dale for longer than that.

Where do you start first: marketing or sales?

It depends on the problem that you're solving.

Great answer. I'll take it. I'm gonna pull this question out from the Wayback Machine. What song would best describe your revenue strategy?

Workbench by Britney Spears.

Oh, I like it. I like it. Early bird or night owl?

Night owl.

What is the first app you check when you wake up in the morning?

LinkedIn.

All right, two more. What's your favorite guilty pleasure snack?

Diet Coke.

Is that a snack? Not really. Snacks, food. I mean, I guess I feel really guilty when I drink one because it's like really basically poison. So that's why I. Yes, fact. Yeah, it's like a treat. Like, I'm like, "Oh, this is so bad."

What's your dream vacation destination?

Ireland.

Oh, nice. Very nice. Top of the morning.

Rachel, thank you so much for spending some time with us. Where can folks find you and all things Gap Selling? I'm going to assume LinkedIn, but where should we go to learn more? Where could we book a call?

Yeah, well, you can find me on LinkedIn at Rachel May Mae. I'm the only one. So hit me up there if you need anything. If you have questions, if you want help, like I'm open. And our website is SalesGrowth.com. And you can buy Gap Selling on Amazon.

Awesome. I love it. Rachel, thank you so much for joining. We appreciate it.

Rachel: Thanks, guys. Bye.