Ep. 7 | The Future of Revenue Enablement in the AI Era with Sheevaun Thatcher - Part 1
The Selling Economy, hosted by Jeff "Yosh" Yoshimura. Guest: Sheevaun Thatcher.
https://www.youtube.com/watch?v=G5kxrFw0-NI
Transcribed automatically from the episode audio.

[0:01] Somewhere out there right now, a sales rep is walking into a meeting and sitting across from them is a buyer who already knows more than they do. That's no accident. AI has created the biggest shift in selling in 30 years and millions of sellers and the leaders behind them are living it every single day. I'm Yosh and this is the selling economy, a show about the people in the middle of that shift and the stories of what's working now and the lessons that they've learned along the way. The selling economy is presented by Any Key, the team behind every rep. Hey there, I'm Yosh. Welcome to the Selling Economy podcast, the show about how modern revenue teams actually sell, train, and win in the AI era. My guest today is Siobhan Thatcher.

Meet Sheevaun Thatcher: Building Revenue Enablement at Scale

[0:47] Over 20 years, she's built enablement functions from the ground up, scaled teams from three to more than 150, and has helped take companies from 300 million to over 2 billion dollars in revenue. Today, she's the VP of revenue enablement at Demandbase, and a 2025 GTM AI Award winner. Siobhan, welcome to the show. Hey, Jeff. How are you? I'm doing great. Well, first of all, I think we have to start off with the Hawaiian shirt. What's the inspiration? What's the love for Hawaiian shirts? You go first. Maui is one of my favorite places on Earth. There's nothing like the plane door opening and going, "I'm here." And [snorts] I just love Hawaiian shirts. I think Hawaiian shirts make people happy because they're not boring and I have probably 100 of them. All different types of styles, some funny, all different.

Hawaiian Shirts and Personal Connections

[1:33] And so, I just I love to wear them. They're comfortable. I think they're entertaining, and they just make me and people happy. I share a lot of those same experiences. I do not have 100 Hawaiian shirts, but I probably have at least 20. And I think Hawaii is my happy place. I think any island, anytime you're outdoors is a happy place. And I agree, it kind of takes you out of the element that we're so used to, which is we're in front of our computers, we're in meetings. And when you you think about kind of the beach and Hawaiian shirt and the islands or a beach, what it brings to you is really happy thoughts. So, excited to really chat with you about everything that you've done in your career, your journey, and what you're doing with AI today. But, I'd love to start off with like tell us about your journey into sales enablement, revenue enablement. How did it start?

Sheevaun’s Journey Into Revenue Enablement

[2:19] How did you end up becoming a master of this trade? Well, I have a jungle gym career. It's not a ladder. There was no going from here and up we go. No, I was all over the place. Couldn't make up my mind. Tried a lot of different things. I think I settled on solution engineering, right? Pre-sales, back a long time ago. And I did it for about 25 years. And then back in 2008 during the recession, I worked for a visionary SVP of sales, Eileen Vote. And on a February morning, she called me up and she said, "Okay, times are hard. So, either you take this package that we have for you or I'd like you to do this other thing." And what is that other thing? She said, "Well, all that stuff that you do with the pre-sales people, I want you to do it for everybody in sales." And I was like, "What does that mean?" And she goes, "I don't know. Make it up. Whatever you're doing over here, do it for them, too.

Beyond Onboarding: Measuring Business Impact

[3:06] Make them ready. Make them prepared." And that's really where enablement for me started. It wasn't called that at the time. We didn't sales enablement as a term didn't show up until 2013, 2014. But, my first role, and I got to make it up myself again, was the VP of global success metrics. So, even back then, I knew the data had to What was that role called back in in those days? There wasn't one. It was just kind of initially it was onboarding. I was doing onboarding. And I thought, "There's got to be more than this." So, it was onboarding and then it moved to how are we going to do what's now called everboarding? How are we going to continue, right? Continuing education. And then what do we decide that we're going to do? Like there are multiple phases I went through with this. Finally to the phase where it was like, "Hey, maybe I should ask other people's opinion and work together with, I don't know, the folks that are closest to the field and closest to the customers and figure out what really needs to be done.

[3:57] How do we really move the needle? How many people went through a course and what their average score was and all of that. I'd call those vanity metrics and they're important for me to know as a leader to make sure our courses are hitting the mark, but the relationship I have with the people that I report to and how I show that we are not just a cost center, we're actually an investment in an organization is around productivity. How do we move the needle? How do we influence the movement of that needle? And attrition. How did the courses give people professional development? How did they want to stay here because they were getting coached? How did Right, all of those things. So, attrition not only internally of our people, but reducing churn of our customers as well because they were getting a different experience from the people that we had worked with. Yeah, I think my first kind of foray into to sales enablement was sales training. I was like Miller Heiman training and the complex sale.

[4:44] And then when I went over to Salesforce, I was part of the deployment team. So, my job was to set up and configure the application and then we'd have a a training group that would go we call it enablement, right? We so we train and enable the teams that we deploy. And then we'd work with the system admin to do ongoing training and best practices, but it was all more around how to use the application versus what I think the strategic aspect of sales and revenue enablement has come to how it exists Yeah. Yeah, yeah. When I talk about it, the really important thing with enablement, especially in an organization, is to ensure that our charter is understood. And when I talk about a charter, it is what do we do and even more importantly, what don't we do? Because typically enablement teams are the dumping ground, right?

The Four Pillars of Revenue Enablement

[5:31] It's like that, "Hey, give it to Mikey. Mikey will eat anything." I mean, we're the fixers of broken things. Scott Santucci said that years ago and I've never forgotten it. It's like, "Oh, look. Hey, let's give it to them." And I think I've told you, right? The scariest words to any enablement person is, "Hey, I've got a great idea." It's like, "Okay." But, I had to come up with a charter and that is what I call the four pillars. And the four pillars really helped me describe to organizations what enablement is and then I talk about it being a business within a business, which talks about what it is, but also what it is not. And so, I'll get there. But, the four pillars are The first one is did they get the memo? Does everybody understand what the go-to-market is? Because all too often, the go-to-market is decided at the board, it's decided at senior execs, all of that, but nobody ever gets told. It doesn't trickle down.

[6:17] And so, folks are never told how they fit into the whole picture. What puzzle piece are they? They're never told that. And so, it's really important that people understand how does their work contribute to the success of an organization. So, that's did they get the memo? Did everybody understand what the go-to-market is? The next pillar is all of our assets, all of our content, everything that we're using, scripts, decks, data, is that all aligned with the go-to-market? Because when you start looking into content systems, for example, you'll find, I know I've been at different organizations where I come in and there's 15 or 20 corporate decks. It's like, which one is right? Right? There's no way to determine which one is correct. And so, the sales people that have been here for they just go off and create their own. So, you have no idea what the messaging is. So, it's really important number two, everything is aligned on the go-to-market and there's one version of it.

[7:06] Can be customizable, but there's one version that people are working from. Number three is are they getting what they need in the moment of need? So, it's like just-in-time enablement, right? Or activity-based enablement is what I'm calling it. So, if you are just starting with an organization and we're doing onboarding, I'm not going to teach you how to do a proposal because you're not going to be doing a proposal for likely a number of months. And anything I teach you right now is a waste of time because it's going to go in and out. That's not going to stick around. The fourth one is tribal knowledge and this is the one that gets missed by most companies. This is making sure that whatever it is you're doing, you're actually checking to see if it's working. You're talking to your customers, you're talking to your sellers, right? Are we hitting the mark with this? If we're not hitting the mark, let's stop doing it as soon as possible.

Capturing Tribal Knowledge Across Revenue Teams

[7:54] If we are hitting the mark, let's make sure that everybody in the company knows it and it's proliferated everywhere. That's pretty much the four pillars. Now, each one of these leads back into the others and you go again, right? So, it never stops. It's constantly the a movement. Yeah, could we dive into tribal knowledge? I find that kind of fascinating topic because it's so hard to do, right? Because historically, right, we've asked reps and customer-facing teams to input that data through activity records or through fields inside of CRM. And then came the advent of conversational intelligent tools which could now record or transcribe or even in a Zoom or Google Meet, you can record a call. And now today you have AI note-takers that can also sit alongside calls and do extremely rich detailed job of transcribing.

Learning From Lost Deals and Customer Conversations

[8:40] But those are all bespoke things that are happening. How do you take all this information that's being consumed, delivered, listened to, and bring it back into the company for tribal knowledge? What is your perspective on that? That seems like a a very hard challenge. The bigger the sales organization is, the more global it is, the more products they sell. What's your thoughts there? a couple of things. Number one, I chuckle when I get into Zoom calls in the first five people there are all the AI recorders. There's not one human yet, right? It's just like, okay. So, and that's fine. But when it comes to the tribal knowledge piece, what are we trying to solve? What is the gap that we're trying to look at? It's impossible to go and say, "Give me all of the Gong calls we've had over the last 10 months and tell me some themes." Ok- okay, great. But is it giving you what you really want to know?

[9:27] The thing is, what have we seen in the data that says we might have an issue or there might be something there, right? Or do we have a new competitor that's come up or whatnot? Use specific things that you're going against this communication software for. Have a specific search that you're looking for. Get that data, then from that use your experience, use your knowledge, use your insight, use your gut to determine does this seem right or not? Then you validate it. Everybody does win-loss reports, they do that kind of stuff. That's great. Everybody loves talking about wins. No one likes talking about losses, but in fact the losses is where all the learning occurs. So, you have to. And I find that I get most of the loss information from these communication software packages because the people that are losing the deals don't really want to talk about it, whatever the reason is.

Using AI to Ask Better Questions

[10:15] So, we can really dig in using those tools. But again, you have to be smart about it and make sure that it makes sense that what you're hearing and what you're seeing and the data that's coming back does seem right and validate it. Yeah, do you think that's easier to grab now or to get that data now with the use of AI and the advance of all the tools? Oh, yeah. It's the advance of all the tools has definitely helped us gather the information provided we're asking the right questions. If we're asking the wrong questions, you'll get an answer back just as fast, but it'll be a wrong answer as opposed to asking the right questions and getting the answers back. And that's where the experience comes in, right? I know a lot of people are like, "We're just using AI for all of this." And I'm like, "Okay, but what if AI doesn't know what questions to be asking, right?" So, there's only there's so much automation you can do. And I know we're going to talk about AI at the end, but I just want to do a caution.

[11:01] Make sure that you're looking at the data to make sense about what you're asking the AI to get Yeah, it's otherwise it's garbage in, garbage out. You're not going to get the right answer. That can Yeah, that's how it's been computing since day one, right? You put garbage data in, you're going to get garbage data out. And I laugh when people are like, "You're doing all their competitive stuff using AI." Because AI is plumbing the big bad internet, all it's seeing is marketing. It's seeing marketing information. So, if you're using that as your comparison, then your comparison marketing and your spin is being measured up against their spin and the answer is who spins better. It's not necessarily the truth. Yeah. That's it. I like who spins better. I can just just see that. Let's talk about R2N4. I've heard you mention this on various podcasts that you delivered. What does R2N4 stand for?

Introducing the R2N4 Framework

[11:48] So, one of the things that comes up a lot in enablement is who is responsible for what when it comes to these programs, right? A lot of times enablement gets blamed if sales didn't do well. And I had to come up with a way to make it very clear who does what and why. So, R2N4 stands for responsible to not for. We are enablement is responsible to the customer-facing organizations to give them the best possible programs, best possible marketing, best possible documentation assets, communications, so that they can have the conversations with their customers that allows the customers to come first, right? That's our job. Now, we are not responsible for the sale. Could we close business?

Responsible To, Not For: Defining Accountability

[12:33] And could we be sellers? Probably. I think we all have the experience to do it. Mostly most of us have have all done it. And we're not there for whatever reason. Mine is because I was very risk-averse. I'd hated the end of every quarter and every year wondering, "Oh my god, I just didn't want the pressure." So, I got into enablement because I still understood sales, but it allowed me to do it. So, responsible for means that the sales managers uh sales architecture leadership are responsible for the execution of any program. What I mean is this. So, let's say we determine that we have to do more multi-threading within an organization. So, we do an enablement program around multi-threading. How do you make sure that you ask the right questions, right? You think a nine-box. Yes, that affects you, but how else does it affects others in the organization? We do all of that. Then, the program itself and the execution of that has to happen by the sales managers on up.

[13:26] Because if they are not involved and they are not accountable for the execution of this, and all it takes is one influential manager to go, "I don't want to do it." The program is going to fail. It doesn't matter how much money, how good the program is, how good your enablement people are, how much investment's done by your corporate investors, it's eventually going to fail because it doesn't have the support and the accountability to success. We have agreed our two-in-four assumes that there is a partnership between enablement and sales, and we have agreed these are the KPIs we're aiming for, this is a hypothesis of what great looks like and how we're going to move the needle, and this is the goal we're after. We'll create the programs, you execute to hit that goal. Because if either side of this doesn't work, then none of it works. How do you think about in a large organization, how do you deploy that at scale? Do you start with the CRO, for revenue leader, and then the line leaders, or do you pilot this in one group or two groups?

Scaling Enablement Across Large Organizations

[14:18] It depends on what it is we're doing. So, if this is a major process change, right? Let's say we change the CRM, or there's a major whatever it is, right? Where it's a daily thing that they have to do differently now, that I use we use a waterfall approach to that, which means the very first person that sees it and gets involved is the CRO. Very first. And it's like, "What are you trying to accomplish? Why is this change been made? Help me determine how you think it should show up." And then we do the first iteration, run it by the CRO, and get the CRO's nod. "Yeah, yeah, that looks that's Yeah, that's what we're after." Then we would go the next level down. That the CRO's direct reports. And it's the same with them. Now that we have this idea, now each of you that has your section, does this align with you as well? Right? Here's the process change, how is it affecting you? Is it affecting all of you? Maybe it's not affecting this group, it's just affecting these.

Driving Organizational Change Through Leadership

[15:05] And so they get they get invited to audit, which in other words is we're training them, but we're not telling them we're training them. So, they get to audit the program. Once that passes there, then it rolls again. Rolls down to the next level. They get trained, and down and down until it hits the people on the street, right? It hits the the sellers themselves. And so everybody above that seller already knows the change, and so there's no reason the seller won't do it, cuz everybody else knows and is aware of it. And two, the folks above them can support them in doing this new change. So, that's a process. If it's product, it's slightly different. So, with product, and you and I talked about this, right? This is the sales and marketing thing, right? There's a lot of head-to-head with that, where marketing will say, "We create all the stuff, product sales never uses it." And sales is like, "They never create anything we want to use." And I came across this very very company I've ever been at.

Bridging the Gap Between Sales and Marketing

[15:55] And so it's like, "Okay, well what does marketing really want?" Well, marketing really wants adoption. Hmm. What does sales really want? Well, sales wants content that is in the language of the customer. So, how do we do that? Okay, here's how we do it. We say, "Marketing, you have a new brochure, a new product, something you want coming out. Great. Give that to me. However, I need two questions answered before we do the training. So, the training starts with two things. First thing is, what's in it for the seller? What are they going to get out of this? Is this going to allow them to open more doors? Will they be able to sell more product? Is it going to increase their comp? Will they be able to go on their Hawaii vacation this year, right? What's it going to give them? And the second thing is, how is it going to help customers buy from them?

[16:44] Marketing all too often says, here is how you should sell this to the customer. Marketing isn't marketing for a reason, sales isn't sales for a reason, and there's nothing like a salesperson being told, here, here's how you sell. Don't do that. Instead, what you want to do is you want to provide the five to 10 open-ended questions that can be used with a customer to accomplish whether or not the customer sees value in what it is that you want to talk to them about, this new product thing. So, do they see value? If they don't see the value, can you describe the value to them so then they do see value. If they don't see that, there's a good chance you're calling fodder, which means, can you reset their vision so they're looking at it differently? Is there Is there something that maybe they're not seeing that you have? So, that's where you need some insight. Can you reset their vision?

[17:30] And if none of that works, then they likely don't need this. And get to know, N O, faster, right? Figure that out. But those are the questions coming from marketing. And then when sales gets this, they have a full complement of curiosity questions that they can ask to have a different type of conversation. They're not trying to sell them demand base. They're trying to ask them, what are your biggest gaps that we might be able to help you with? And if we can't, maybe we can tell you who can. Yeah, I think that's that's brilliant. It's such a hard thing to do in practice because by nature, we all like to touch and feel things. So, because of that nature, we go straight into the feature, straight into product versus attempt to elevate the conversation to value. The problem is when you go into product and feature sell, it's like a page on a clipboard, and all you're doing is check, check, check.

Moving Beyond Product Features to Customer Value

[18:20] And then what happens? It just comes down to price. You haven't shown value, you haven't shown anything, you've just said, "I've got a better bid twiddler than you do." And you're never going to win that way, right? It's got to be around value, it's got to be what are they going to get out of this? Then you can talk about what are the features that might support Well, this is a good place to pause. We just walked through our love of Hawaiian shirts, Shavon's journey into enablement, and what she's doing today, her four pillars, and her R2 and four framework. Stay with us, and on the next episode with Shavon, we'll dive into what she's working on now, and her perspective and point of view on AI. That's the show. If this one sharpened how you think about selling, send it to one person on your team who should hear it. Follow the Selling Economy wherever you get your podcast, and subscribe on YouTube so you never miss a conversation.

Closing Thoughts and What’s Next in Part 2

[19:11] To learn more about anything, visit anything.com. New episodes every Wednesday. I'm Yosh. So long. Thanks for listening.