Sheevaun's Role at Demandbase

Alex Kracov: So you joined Demandbase about a year ago. Let's set the stage for the listeners who are maybe not familiar. What does Demandbase do? What does the go-to-market look like that you help support?

Sheevaun Thatcher: So Demandbase helps B2B companies focus sales and marketing and make sure that the accounts they're trying to sell into are the right accounts. So it helps them with pipeline growth. It helps them avoid missed revenue targets. It helps them with sales and marketing alignment. And it helps them essentially waste less budget, pretty much.

Alex Kracov: And so how big — how many sellers are you supporting?

Sheevaun Thatcher: I've got about 300 across both acquisition and retention side of the business. So the new business side as well as growth and expansion in the CX side — that also includes professional services, the pre-sales folks, so solution consulting. And of course my team.

Joining an Established Company: Priorities and Early Focus

Alex Kracov: So what does enablement kind of look like when you first join the company? And I'm curious — when you join a company that's obviously established and has 300 sellers, how do you think about priorities? How do you sort of think about tackling, you know, building out the next generation of the enablement program at Demandbase?

Sheevaun Thatcher: So a lot of what I did when I first started — well, first of all, when I started, it was the fixture of broken things, right? I know, it's a problem, dumping on enablement. That's what it was. There wasn't a leader here. So enablement folks, just by their very nature, were in service. And so we say yes a lot, regardless of whether or not it's something that should be done. And so I spent my first two to three months meeting with all the sales leaders, meeting with the CEO, the CFO, the CMO, all the PMM folks, just to get a handle on where we were and what we were doing.

And then the very next thing I did was, first of all, ensure that the team that I had was the right team, and then making sure that the projects we were working on were the right projects, because frankly, 60% of them were ones that weren't aligned. I have something called the five questions — and I'll go into that later — but it was teaching my team how to make sure that what we were working on was not only the right things, but had been agreed upon with our strategic partners who are sales leadership and frontline managers on up. Are we actually doing the things that are going to move the needle and move the needle now, not move the needle in six months or a year?

The Five Questions Framework

Alex Kracov: Because you brought it up, I'm curious — what are the five questions? I assume that helps with the prioritization framework of all the things.

Sheevaun Thatcher: Yeah, I'm happy to. The hardest thing for us to do is always to say no, right? Or not yet, or not us. And so the five questions — I actually wrote a LinkedIn article about it. The first one is: how is this aligned with go-to-market? This project you want me to do. Now, this is whether it's someone on my team, somebody in sales, somebody in leadership — if they're coming to me and asking us to do something, these five questions go out. So the first one is, how's it aligned with go-to-market? Now that is predicated on the hope that there is clarity in go-to-market, and so that's also part of what I work on — that clarity piece.

The second is: given everything we're already doing — not just for you, but for your team, for our division, and for the company as a whole — where does this fit in the priority? And of course, everybody says it's priority one. And my response is, if everything's a priority, nothing is. So let's start with what you've already asked us to do. What are you willing to push? What are you willing to stop in order for this to be worked on? And a lot of times they go, nevermind. I'm like, yeah, exactly.

The next one is: how are we going to measure it? And what I hear a lot is, we want them to learn it, or we want to make sure they take the training. That is not what I'm asking you. What I'm asking you is, what do you expect is going to change from now that is going to show that we are making advancements — either in performance, reduction in attrition, reduction in churn, something along that line? Give me business KPIs. I am concerned about the vanity metrics for enablement — that is not your concern. Your concern is are we doing the right things? Are we measuring it appropriately? Because if we don't have a measure, what's the point?

The fourth one is: what behavior do you expect to change? What do you want them to actually do? Make more calls, access more LinkedIn, do deeper research, not spend as much time on administrivia — whatever it is. What do you want them to physically do?

And then the last one is the urgency. Is there credible urgency to this? Or is it a, I just had this idea? As I tell people, the scariest five words to me in enablement are, "Hey, I have a great idea."

Alex Kracov: Especially now with AI, everyone's got a great idea.

Sheevaun Thatcher: I'm like, Lord, okay. And so that's where the five questions come in. Because it comes from everywhere — the CEO, the CRO, I've had all of them: hey, I've got a great idea. And we have a chat about, is it really a great idea? Now? Maybe it's something for later? So that's the five questions. And it was those five questions that I taught the team, and then we evaluated and investigated everything we were working on to see whether or not we actually had that data. We created an Asana spreadsheet — they already had an Asana sheet, but it was just: here's the person who requested it, here's when it's due. Nothing else. And so we expanded it to include these other pieces. It was a learning opportunity for not only my team, but also for the folks internally, because they weren't used to answering those questions. It typically was, hey, give it to Mikey, Mikey will eat anything. But it really helped get my team focused and gave them the ability to say no, or not us, or not now — through these series of questions.

Alex Kracov: It's a great framework. Prioritization was one of the things I learned as a young exec. I used to work at a company called Lattice — it was my first job, I was the third employee there and then became the VP of Marketing. There's a million things you can do, a million ideas from the CEO. I had a marketing coach at the time who was like, let's just do a simple exercise of above the line, below the line, the five things we care about. It saved me. If you don't have that prioritization at the beginning, you can't be successful as a leader. I really like this framework. It's a good way to approach it.

Team Structure at Demandbase

Alex Kracov: I'm curious — maybe flash-forwarding to today — how is the enablement team structured at Demandbase and how do you sort of think about that structure?

Sheevaun Thatcher: We have a small and mighty team. I've got five enablement folks and I've got two designers. The designers are actually creating e-learning for our customers — I adopted them about two months ago. But in my enablement team, there is a tools and PMO person, a project manager kind of person. I have somebody who does product, who is liaison between product and enablement and the salesforce. I have someone who is field enablement and he covers not only new business but also growth and SDRs at the moment — we're desperately in need of another person. And then I've got someone that covers the CX side of the business. So growth is more the, we're told a customer is interested, now we go in and try to sell it. Whereas CX is more the customer discussions and support and all of that. And then one person who does onboarding.

Alex Kracov: Makes sense. And so you have them sort of structured against the funnel and then each of those enablement folks kind of partner with someone on the sales team or the CS team and work together on the enablement roadmap?

Sheevaun Thatcher: Yeah, I mean, that was part of what I gave them too. By having the five questions, they were able to say, we know what we're doing and now we can have an actual voice. That was where they really struggled — they were being directed instead of believing in themselves and relying on their knowledge and experience in these types of roles.

Moving from Product-Led to Value-Based Selling

Alex Kracov: Do you have a top-of-mind example of something that the enablement function brought to the table — pushing the sales team or CS team toward a program you wanted to put in place, as opposed to being directed from the sales side?

Sheevaun Thatcher: I think there's a few things. One is the company had been product-led for a long time. So most of the sales opportunities, when you listen to calls and all that, it was product, product, product, product, product. The problem is — and this is something I worked very hard to get across, and the good thing is the CRO who started probably two months before me feels the same way — it's got to be a value-based and a customer-first conversation. Otherwise, you're simply a list and a set of checkboxes on a clipboard and then it's yes, no, yes, no, how much is it? And that's what it comes down to.

Demandbase is an investment. It's definitely not the most inexpensive out there — for a reason. There's a ton of capability in it. But I didn't want them to continue doing the product sell. And so we moved from that much more to a value-based approach. It's not value-based selling in the traditional sense, but it was: what are our customers really dealing with? ABM is a capability, it's a type of tool, but what is it solving? And so we looked at things like, is it missed revenue targets? Is it sales and marketing alignment? Is it bad data? Is it lack of account knowledge? Are they actually reaching out to the right people, or is it just a scattershot hoping that somebody is going to nod and say, okay, talk to me? That's really how we transformed, and are continuing to transform, how we go to market.

Alex Kracov: And there's something very meta about enabling sellers to sell an ABM tool and sales intelligence, right? Like I assume you're using the tool to sell. Does that shape your enablement work? Does it make product education easier?

Sheevaun Thatcher: Well, I would say that for a long time, Demandbase was Shoemaker's children, right? We were selling something and not necessarily using it, or weren't aware we were using it. Like our DB1 for sales — everybody was using it, but it was hidden behind Salesforce. Now we've made a concerted effort to say, no, we want you actually interacting with it all day long. You need to be able to understand. And I think it was that that gave our sellers the empathy and the knowledge of how this was actually helping them.

Because ultimately my stakeholder is not my internal folks. My stakeholder is my customers' stakeholders. Because what we are doing is helping them provide for their people and for their customers. So if those folks aren't buying from our customers, our customers aren't buying from us — and there you have it.

Alex Kracov: Yeah, super interesting. It's a very similar dynamic at Dock where we're an enablement tool — we create deal rooms, we sell to our customers, but it's only successful if our customer's customer is successful using it and getting the value they need as an end user. Very, very interesting.

Building a 162-Person Enablement Team at RingCentral

Alex Kracov: Going back to the team-building stuff — I know you've led much bigger teams. You were at Salesforce and Slack and RingCentral. You saw a lot of growth — went from three to 162. What does a 162-person enablement team look like?

Sheevaun Thatcher: We started out, of course, with a smaller group of salespeople. We ended up supporting initially about 200 people and we ended up supporting 10,000 by the time I left. So as the sales teams moved upmarket and got bigger, we got bigger because we had to make sure that we were able to support them the way we did. We were restructuring, doing the things that needed to be done so that enablement could support.

Then, around year three, I realized that the only difference between what I was delivering and what the rest of the company needed was how they were gauged on performance. Everything else was the same: how does it align with go-to-market? Do you all understand the message? Are you using the websites properly? Are you producing content that aligns with go-to-market? Are you making it easy for folks to find this information? And then the last part is how are you gauged, how are you measured on performance? That was the only difference.

So I went to senior leadership and said, I want all of it. I want to enable everybody in the company because what we're doing on the sales side with onboarding and with all of that is much more structured — so the rest of the company could definitely take advantage of it. They could take advantage of value-first discussions. They could take advantage of understanding the company.

One of the first things we do with new hires — especially on the sales side, and we do it here too — is: here's why the company exists. Here's why Demandbase exists. This is what we are helping customers solve. Here are the customers we work with. Here are the products we have and how they fit into all of that. Because what I discovered is outside of the sales organization or PMM essentially, no one else knew the answer to that. Nobody knew the origin stories. Nobody knew any of that.

I know from my own experience at RingCentral — I had half a day for onboarding. They gave me my laptop, said here's how you get to your benefits, which of course I forgot immediately, and here's a desk. I didn't know the tools. I was a month in when my boss came to me and said, you have to stop sending me emails. You need to use the internal messaging system. I'm like, I don't know how to use it — Glip, I don't know how to use it. And he sat down beside me and gave me like 15 minutes. That's all I needed, but nobody was getting that. And so we took over the whole onboarding for the company. We took over supporting engineering and everybody. We were doing enablement for the whole thing, and that's kind of how things grew.

We also took over customer training and turned it into a revenue stream where it wasn't before. Customer training was always the first thing on the invoice that got scratched. We're going to discount by not charging you for any of the training. And so one of the things I said is we're not going to do that anymore. Number one, we've got 30 trainers out here who don't know whether they're valued at all — because you're not charging anything, customers maybe show up, maybe they don't. So I said, we need to change that. We have to deliver it in three different ways. If they're willing to take training right off the website, great, zero dollars, knock yourself out. If they want instructor-led, it's going to be a certain price. If they want us to go on site, it's going to be more. If they want us to customize anything, it's going to be even more.

So we changed it so it was five thousand, ten thousand, twenty thousand. And they're like, that'll never fly. And I'm like, you watch. Because all of a sudden there was a line item on the invoice that people could see was being discounted. Here's how much they were getting. But also folks all of a sudden thought, it must be really valuable. And so our first quarter once we did that, we had a quarter of a million dollars in pipeline. We closed half a million dollars by the end of the second. Closed. Revenue. For this brand new stream. It's just because we looked at things differently.

Alex Kracov: And it makes the customer more committed to the training too. If they're going to pay 5, 10, 20K for it, they're going to show up, they're going to take it seriously, then they onboard your product. As somebody starting a company, you're always scared to charge low — but the more we charge, actually the better the customers are because they're more bought in and willing to work alongside you.

Sheevaun Thatcher: Right. They perceive value. If they're getting something for free, they think it's a throwaway. If they're investing, there's perceived value and they will follow up.

World-Class Onboarding: The Three P's

Alex Kracov: So you gave an example of what bad onboarding looked like when you first started at RingCentral. But what is good onboarding? What is world-class onboarding? Maybe we could talk about what Demandbase's onboarding program looks like today.

Sheevaun Thatcher: Yeah, Demandbase's onboarding program — it's all around the three P's: people, process, product. So we spend a lot of time around people and company — getting them to know the origin stories, getting them to understand our customers, understanding use cases. Why do customers buy from us? So the whys: why are they buying, why are they buying now, why are they buying Demandbase? All of that is done upfront.

Then there is the process piece, which is: here's how we sell at Demandbase. This is what it looks like. We're using the Spiced model from Winning by Design. We're using nine-box models from Solution Selling. There are all of these pieces — get them to understand how we sell.

And then the last part is product, but that's very light. I remember talking to somebody who said they had a three-month onboarding and they were losing people after a month and a half. And I said, well, tell me what it is. And they said, we spend the first two months on product and we go deep, deep, deep, deep on product. And I'm like, well, no kidding. They don't need product that early. They need to know kind of what it is and kind of what it does and what customers buy from us. But going deep on product — they need to be able to have conversations, not go deep on product. They have to have value conversations, not product conversations.

So it's always light on product. And as they get more experienced, we make sure that they can fish for the things they need. But not just fish for all of this stuff and put it all in a basket and come back to it six months later — that's no good, it's dated. Rather, it's teaching them how to fish in the moment of need and how to fish for what they're really looking for. Not just throw the lure in and hope you're gonna catch something. It really is precision over volume. We want to be very precise on that.

Alex Kracov: Is there like a capstone to the onboarding where they get in front of you or other managers and have to practice a value-sale pitch or qualification? Is there a certification thing?

Sheevaun Thatcher: Yeah, the platform we use has an AI coach and an AI role play capability. So we can have them do AI role plays over and over again for various types of personas, various types of customers, markets, all of that. And then at the end, they have to be able to present back. They record themselves and upload that recording to the platform and their managers, senior managers, and our enablement folks all go in, take a look, and comment to make sure that the manager knows who they're getting on the next week. So there's a lot of self-serve learning in there. But AI has really made a difference when it comes to that. We don't need to involve the frontline managers as deeply as they would have needed to be involved in the past.

Alex Kracov: Yeah, it's crazy. The AI role play space is blowing up. I was at an enablement conference two weeks ago — how many vendors and things. It's super interesting. Do you use it mostly on the onboarding side? Because I've heard it's super valuable for onboarding, for cold calling, for younger sales folks — but maybe more tenured reps are not using role play?

Sheevaun Thatcher: We go across the board. I don't care if you're 100 or you're 10. You have to role play. Because if you don't role play and you don't practice, it's not going to stick. I don't know how many SKOs I've been at where it's, we're going to do all this fabulous training, and there's no follow-up. And there is a surprise two months later — they've just come back to the way they did it. It's because you didn't reinforce it.

I think it's the Ebbinghaus curve — after 30 days, they only retain 7% of what you taught them if you don't reinforce. So with these AI role plays and AI coaches, we push everybody through the platform. Now, it doesn't mean they're all taking the same thing. It's precision over volume — not everything needs a certification, it can be a knowledge check. The ones with the least experience — like BDRs, SDRs, maybe small business — they probably need a little more coaching and knowledge checking when new stuff comes out. Whereas when you've got high performers, my advice is just get out of their way. Make sure they know where to find everything. Give them the rod and the reel and the lures, but let them go get it when they need it.

Because forcing everybody through certifications and the same stuff is just ambiguity and a challenge. And the moment somebody is taking something that doesn't make any sense, you've lost them. From that point forward, it goes from being something they really want to use and a choice for their performance, to a chore.

Coaching Managers: The Biggest Gap in Enablement

Alex Kracov: Totally makes sense. One of the important things you mentioned was what happens after the training — the reinforcement side of things. And obviously managers play a really big role in reinforcement post-training. I've heard you say the biggest failure is that managers don't always know how to coach — not because they won't, but they just don't quite know the best way to do that. Why is that such a problem and how do you overcome it?

Sheevaun Thatcher: I think there's a variety of reasons. Number one, it was never a focus for a long time for most companies. The focus was, what have you done for me lately? Let's look at pipelines, look at forecasts. Didn't look at skills, didn't look at any of that. Now the really good managers did, but it wasn't a consistent program. And so as you have high performers moved into management roles — big mistake, by the way, because the high performers do it because it's an unconscious competence. They have a really hard time telling people what they do. But as you have AEs moving into management roles, if they haven't been coached on how to do it, they're just going to play what they've learned, which in most cases is just going to be the pipeline and forecast stuff. And it's just not going to fly, it doesn't work. It doesn't mean they don't want to, they just don't know.

So we spend a lot of time saying: if you're doing a pipeline call, focus on pipeline. If you're doing a forecast call, focus on forecast. If you're doing account management, focus on that. Skills — don't forget the skills, focus on that. Keep the one-on-ones focused with a regular schedule and cadence. Make sure they're happening at the right time, you're asking all the right questions, and you're actually getting in and investigating what is actually really going on.

Alex Kracov: And like, how do you develop those skills? Are you doing manager offsites? Because I assume you're not listening in on people's one-on-ones with their reps. How do you get insight into how they're even doing coaching in the first place?

Sheevaun Thatcher: It starts really at the root of the request. And it's like kids — if you want kids to do something and you get them involved in the decision, they'll do it a lot more. That's the same with any type of enablement you're doing. If you get them involved in the discussion, if they're involved in the five questions, if they're involved in giving you feedback on what's really working — if you've got that corporate intelligence and customer intelligence they're bringing in — get that early so that what you're doing is going to land.

Then when you roll it out, you roll it out to managers first. They're involved in all of this. They are auditing — as opposed to being trained, they're auditing to make sure they're on the same page. So by the time it gets to the feet on the street, everybody above them has already done it. And I mean everybody above them.

Like we did a big pitch contest for our RKO, and the CEO reached out to me and said, I want to do it too. And I was like, God, I love you. So he was one of the first ones to do it. And they were all rated — the AI coach went in and gave them scores, and their peers had to go in and give them scores. The CRO had to do it, all the SREPs, everybody did. So you have that kind of waterfall responsibility. And when you do that, the managers are a lot more invested. They start to learn. Because it's not just the managers who don't know how to coach. If you go up another level, they don't know how to coach managers. And you go up another level, they don't know how to coach VPs. It's this whole hierarchy of need.

Alex Kracov: And it's super hard. Coming up in sales, you learn how to close the deal and work with the customer, but then you become a manager and it's like, my God, how do I become a people leader? And then it just keeps going up.

Sheevaun Thatcher: Right, exactly. And you have to learn how to do it. Being an AE, you learn how to close a deal. And what you often see is at the end of every quarter it goes into full-on hockey stick — managers are like, I'm just going to go out and close everything myself. But when they get out there, there's no coverage. They can't get enough out there. And so you start to see big discounts and deals slip because they're not spending the time on skills with their own people to say: here's how you close. This is what negotiation looks like. Here's what a pre-proposal looks like. Here's what discovery and alignment looks like between you and the rest of your sales franchise. If they haven't even been taught that, then they won't be closing the deals either.

Responsible To, Not For: The Enablement Philosophy

Alex Kracov: One of the interesting dynamics in go-to-market and enablement is that everyone's aligned to the revenue number. But I've heard you say enablement is responsible to — not for — the business. Can you talk about what that means?

Sheevaun Thatcher: That is the absolute linchpin of this whole thing — of enablement being able to work. Responsible to, not for — hashtag R2N4. What it means is that we as enablement are responsible to our sales managers, frontline managers and up, to provide them with the best possible enablement we can. That could be messaging, product release information, skill training, whatever. It is our job and we are responsible to do that. We are not responsible for the sale.

What that means is we are working very closely in strategic partnership on what we're actually delivering as enablement. Once we are ready to go, it becomes the responsibility and accountability of sales management — frontline manager on up — for the execution of the program. And that is something I get established from the very beginning when joining a company. Because if I don't have that support, it doesn't matter. All it takes is one influential manager to go, hey, I don't want to do it. And it's a house of cards.

If enablement is the stick — you have to go do this — and you're pounding, it becomes a chore. If their manager is saying, for your skills and your performance and your learning, you need to be able to do this stuff — that has a very different connotation. It becomes a choice. And so that is really, really important.

I had a situation where a sales manager, in front of his boss and my boss and VPs and everybody else at a QBR, said that he and his team didn't make their number that quarter because enablement was bad. And my response immediately was, oh, so you wanted me and my team to go out and close all your business for you then? And he said, that's not what I said. I said, that is exactly what you said. Because enablement is only a piece of this puzzle. You're responsible for the sale. You're responsible for the execution of these programs. Because if R2N4 is not established early on, it doesn't matter what you do. It doesn't matter how good your enablement team is, what the resources are like, what the investment's like, what your programs look like — they will ultimately fail.

Measuring Enablement: Vanity Metrics vs. Business KPIs

Alex Kracov: And so then how do you think about what enablement is gauged on, or how do you measure what's working? Are you doing internal CSAT to see what the sales team feels about your programs? How do you think about measuring your own team's success?

Sheevaun Thatcher: All of what you're talking about — those are what I call vanity metrics. They're important to me. I need to know: is this hitting the mark, are we getting the throughput we expect, what do the scores look like, are there teams that are doing it and teams that aren't? But that's not what my stakeholders care about. They care about: is the needle moving? So I can take all of those vanity metrics, but I need to align them with all the performance metrics to say — did this enablement program change anything? Did behavior change? Did numbers change? Ultimately it's sales velocity: did our deal wins go up? Did average sales price go up? Did the length of sale shorten? Did all of those things get impacted?

Because they really don't care about the vanity stuff. And this is why a lot of enablement leaders can struggle — they go in thinking, 98% of the people went through it, the average score was 92 out of 100, and we got great CSATs. And leaders are going, and I haven't seen any difference. So it's being able to have those business conversations. I call it running a business within a business. You have to be able to talk about it like a business.

Alex Kracov: But then how do you reconcile that with the responsible-to, not-for philosophy? Because you have this indirect puppeteer sort of lever to get to the actual number — for you to hit your goals, the sales team has to perform well.

Sheevaun Thatcher: That's the game. That's how it all goes together. They have to perform. There's a quid pro quo. When I talk about my investors — that's anybody that wants to give me anything, could be money, could be people, could be time — the quid pro quo is I have to give them back the results they're expecting for this. And as I give them back those results, I get more. That's how you grow.

And there's the supply chain — that's marketing, PMM, anybody that wants to put something in front of the salespeople. My discussion with the supply chain is: what do you really want? What's the quid pro quo? And their big thing is adoption. You go to any company and ask them how much of the marketing material is actually seen by sales — you'll see numbers like 20%, maybe 15%, maybe 25%. Which means 75% of all the work that's being done by marketing is never seen. It's just lost.

And so they're like, how do we change that? And I said, you change it really, really easily. First thing: don't give me an hour-long video. Don't give me a 50-slide deck. Not gonna work. Nobody has that attention span anymore. Instead, break things up into consumable chunks. Then do two things. The first thing is — if I'm a seller, what's in it for me? Why should I even care about this? Is it going to open up more opportunities? How am I going to get bigger commissions? Is there an SPF associated? What is it? That's how you start.

And then the next thing is: how is it going to help my customer buy from me? Not how is it going to help me sell. Marketing's in marketing for a reason, sales is in sales for a reason. Marketing should not be telling sales how to sell. What they do need to help sales with is understanding how customers are buying. Give me the five to ten open-ended questions I can ask that are going to allow me to introduce this to a customer and see where we sit. Do they see value upfront? If not, can I create value in their mind? If I can't create value in their mind, can I reset their vision? And if I can't reset their vision, get out, move on. How many deals go way past when they should? So expensive, so costly to do that.

It's a very different conversation for most customers. They're used to getting pounded with all of this product info. We don't even talk about product info initially at all. It's all values. It's all those pains I talked about at the beginning.

Relationship with Marketing and Content Strategy

Alex Kracov: I'm curious about your relationship with the marketing team, because you obviously have a very strong point of view on the type of content that's going to work well in the sales process. How does that relationship work between the enablement team and marketing? Are you reviewing every piece of collateral that gets in front of sales? How do you give feedback?

Sheevaun Thatcher: Someone on my team is doing that — that's why I have a product enablement person. She works very closely with that team. Most of marketing is top of the funnel — great, show me what you're doing, but I'm not going to get involved in that. What I do want though is once things start getting down further into the funnel, when we actually start having these conversations, I need to make sure that my folks are armed with the right questions to ask.

Because most companies, when they come to us, most of these customers have already done all their research — especially with the tools we have now. What they're trying to find out is: do you understand their pain? Can you help them solve the pain? Can you have conversations understanding what their business is about and what they care about, as opposed to pounding product into them?

AI in Enablement: What's Actually Working

Alex Kracov: Switching gears a little bit — this wouldn't be a podcast in 2026 without talking about AI. We've talked a little bit about AI sales role play. What AI tools are actually working right now, both for the enablement function and for sales teams — versus what feels like overpromised and underdelivering?

Sheevaun Thatcher: It depends on what group you're a part of. AI is very black and white when it comes to the development side of the company — product engineering, all of that, it's pretty straightforward. AI for everybody else gets a little squishy, and you have to decide what it is you're really after.

Like we've got integrations internally with ChatGPT — everybody uses ChatGPT. So it's teaching them, A, it's available, and two, what can you do with it? Most every tool now has some kind of an AI piece to it. Whether it's real AI or just machine learning, that's still a question. Me personally, I use ChatGPT for a lot of things — pretty simple stuff. If I've got a quick question, go find me, or give me the one sentence that allows me to talk to folks on a webcast about what Demandbase does, right? Which is exactly what I did.

When I get into doing much more complex, much more process-heavy work — a masterclass I just did, I did in about 12 hours what would have taken me four months to do. And I did it myself. With input from the CRO, of course, to make sure he was going to have buy-in on it. But it was going through and gathering all this stuff together, and I used Claude for that. Initially it was just Claude Chat through the project, but then Claude Cowork came out and I was like, ooh, this is good — because now I can save all this stuff, I don't have to start over from scratch every time. I haven't used Claude Code yet. I've also used NotebookLM to take content and say, make a podcast out of it or a five-minute video or these various pieces.

So depending on what I want to do is depending on the tool that I'm using. Internally, ChatGPT is a standard, we also have Microsoft, and we're a Google shop so we use a lot of Gems. It's mostly Gems and things like that. Workflows and agents and all those kinds of pieces that are used not only within our own software that we sell, but also internally with how we do workflows.

It's almost in its infancy because there's still so much to learn. I was talking to somebody earlier today and I've been up and down through troughs of disillusionment — yay, yay, look at this really cool thing, oh, I can't integrate it with anything else. Oh, it's not giving me the answers I want. So you have to be very prescriptive about what you want. You've got to be able to synthesize, reroute, put together the packages that make sense with AI. Where can it be used? Where can it not? Where shouldn't it be used?

Because the downside is if you're using AI for everything, then everything is homogenous. All you're doing is doing what everybody else out there is doing. There's no insight, there's no creativity. The human in the loop is absolutely critical. AI doesn't have intuition, it doesn't have empathy, it doesn't have gravitas. It doesn't have 40 years of experience doing enablement and pre-sales and all of that. So doing this masterclass — yeah, it was 12 hours, but it's because I knew exactly what I was after, why I was after it, and how I wanted it presented. Then I let it go and do its thing. But it was all of that other human stuff that got it to where it is.

Alex Kracov: Yeah, that's because you were driving it. You were driving the AI.

Advice for an Enablement Career

Alex Kracov: I'd love to end today's conversation with some advice for someone who wants to get into enablement, or maybe they're early in their career and want to get to where you are. How do you have a successful career in enablement?

Sheevaun Thatcher: I'd like to say it was climbing an enablement ladder, but it really was a jungle gym. I did all sorts of different things — I was in marketing, I was in development, I was in product management. I came into this actually in 2008, so out of a really bad time came really good things. Because I was running pre-sales at the time and the SVP of sales came to me and said, I need you to do something else. Whatever you're doing over here, I need you to do with everybody. Because I don't have to worry about you, but I'm worrying about all these others. Can you do that? I'm like, what is that? She said, I don't know. Call it whatever you want. You're simply white-labeling this thing. Go do it.

So initially I was the VP of Global Success Metrics, because even then I knew that data was going to be important. But I mean, sales enablement as a term didn't even come out until Forrester came out with it in 2012 or something. It hasn't been around all that long.

What I would tell people trying to get into it is: understand your charter first. Make sure that you have a very strong point of view. Make sure that you understand the relationship and establish the relationship between what you provide and what your sales leadership needs. Now, notice I keep saying sales leaders are my customers, because they are. Salespeople are the lucky end users — they're not my customers.

And a lot of that is the R2N4. I need frontline managers to be responsible for the execution of the programs, so they're my stakeholders. So it's understanding how all of that works, having a point of view, making sure the five questions are asked so that you're working on the right things at the right time — and you're not just a fixer of broken things. That's how we started this, right? If you're a fixer of broken things, you're never going to accomplish anything.

Alex Kracov: That's a great answer. Thank you so much for the time today, Sheevaun. This was a lot of fun.

Sheevaun Thatcher: You're welcome!

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