Enablement Is DEAD: Why Sales Teams Don’t Trust You Anymore with Sreedhar Peddineni

Welcome back to another episode of the Bridge the Gap podcast powered by none other than Revenue Reimagine. Today's guest is Shreder Panini, who is the founder of GTM Buddy and one of the original co-founders of Gainsite, where he helped create an entire category. He's now on a mission to fix what he sees as one of the most persistent go-to-market gaps. You all see what I did there, right? Bridge the gap, go-to-market gaps. Enablement, that sounds good on paper, but actually fails on the front lines. No fluff today. We're going deep on what reps actually need, where most GTM orgs get it wrong, and what enablement looks like when it's built for reality instead of theory. Thanks for joining the show, man.

>> Thank you for having me.

>> Awesome. Let's jump right into it. So enablement as it exists is kind of a joke. Let's start just really out there. Why is enablement broken in most organizations, and where do most teams go wrong with sales enablement? Maybe it's at the definition level, but where does it start? Why is it so broken?

>> Yeah, it's really interesting. So like you, I've been in leadership roles for most of the past 25 years. And whenever we're having conversations at the leadership level, I've never really seen anyone on the leadership team questioning the importance of enablement. Enablement as a need—we're hiring people and our business is changing all the time. The product is changing, new competitors are coming up, the market is changing, and we need to uplevel our teams on a continuous basis. I've never come across any leader in my personal experiences and in my network who questions this fundamental premise that enablement is important, right? But at the same time, we're seeing this, especially with the end of growth-at-all-costs mindset over the past few years. A lot of enablement professionals, seasoned professionals, a lot of well-respected enablement professionals have been impacted by the layoffs and so on. Now, what gives? Why is this happening? There's a lot of this perspective that we hear that, okay, enablement is a good-to-have. When the times are hard, you cut good-to-haves. It's a cost center, you know.

>> Dude, I'm sorry to interrupt you, but you hit a nail on the head. I worked for Toast for many years. We had an enablement team of almost 70 people. It was the biggest enablement team I ever saw. And we'll go into what they did or didn't do, but you're right. Times get tough, the first team that got cut—we went from 70 to three.

>> Wow. That's a massive cut.

>> Don't need enablement anymore. Times are tough.

>> Yep. And a lot of times, people think that, at least, a lot of enablers come with an L&D background, and there's a lot of excessive focus in many ways in terms of new-hire onboarding and ramp time. A lot of that gets talked about. And when in a world where nobody is hiring, there's this argument that comes up: "I'm not hiring, so why do I need enablement?" But you know what? There's not a single technology company out there that I know of which hasn't launched an AI something in their product.

>> There's not a single company that talks about, "Okay, I need to equip my teams with AI awareness." There's a geeky few people who are doing cool stuff with these tools—ChatGPT or Claude or things like that—but the vast majority of people are going into ChatGPT and typing in like they're using it like Google Search.

>> Yeah.

>> There's this interesting statistic that we see in our own platform. We have a ChatGPT-style UI where reps can ask questions and they find answers that are within the GTM platform. And we get access to statistics in terms of how people use the tool. The most common length of a prompt is about three words.

>> Yeah, because they want the easy button. Everything's like an easy button for people. And I want to jump back a little bit to enablement. One of the biggest things when we're working with founders and CEOs and CROs is, "What does our team look like? Is the team doing the right thing?" And then it's always like—I get super nervous because when we do the evaluation, we may need to find additional teammates or we may need to level people up. There's no enablement. And that lift on the enablement side can be very heavy because they don't have the documentation. They haven't done the enablement or the onboarding. But the onboarding itself, they do—like, company onboarding: here's your badge, here's your laptop, here's your blah. But they don't do go-to-market onboarding. And you're spending a lot of money on these people. And, you know, we talk about a cost center from an enablement perspective, but the cost of losing people or having to turn people over is so high that people don't factor that into the team.

>> Absolutely. Just going back to that observation, I guess the question that people are really asking, especially from the leadership side—we discussed how people aren't really questioning the importance of enablement, but really the question seems to be, "How are we enabling people?" The leadership does not seem to be convinced that the way we are enabling the team is the problem. And some of it gets ascribed to the people who are doing the function, whether or not they have the charter or are empowered to do the enablement the right way. There could be any number of reasons. I guess the challenge is people are not questioning the need for enablement, but the question is on how we are enabling people. Now, the moment you talk about the gap—and I believe that gap is in terms of expectations versus reality. Most enablers, when they come on board, like you said, one of the first things that you do is company onboarding. Yes, you do it with new hires: "This is our company and culture. This is the history and this is the employee policies and all of that." That's all needed, right? Fine. But what next? What's GTM enablement about? So a lot of times people would do, "Okay, I'm going to do domain training. I would do product training." And in the traditional world, even not too long ago, I would create a product training course and a domain training course, and I hope that it stays true for a couple of years. I might make minor tweaks and so on. But when change is coming at us at a walk speed, the domain is evolving, the product is evolving, and the competition is evolving, how do you stay current to begin with? Are the enablers enabled to keep pace with the change that's hitting them?

>> So is it the tech, the mindset, or how go-to-market orgs are structured when it comes to enablement?

>> I think—hate to say this—but I guess my perspective is that it's all three of them, right? And that's okay.

>> Yeah.

>> So when you look at the people aspect of it first, things first: enablement needs to feel supported and empowered to begin with. It's a two-way street. And in order to give that trust and empowerment, there needs to be the leader convinced that there's a sound plan that's put together and sees the outcomes. If this plan is executed well, I would see the outcomes, right? It's a two-way street there. That's one issue—the people empowerment gap. And the second issue is about the currentness of the enablement content that I'm creating—call it learning content, datasheets, or compendia that I create, or what not. How current is it? And the moment a rep sees that it's outdated content, they lose trust. And they would download it onto their laptops, maybe tweak it a little, make it their own, they'll keep using it, and there's no coming back from that, right? So if you want to keep the content current, now you move into the technology problem. I could throw bodies at keeping information current at all times. Most companies operate on a bi-weekly sprint. If you talk about product knowledge being current—

>> Yeah.

>> Companies operate on a bi-weekly sprint in tech, as you know. And how do I keep the people up to date? Every other month, there's a significant new product capability that's coming up that needs messaging.

>> And enablement and training, like, it's the challenge—people think it's a one-time thing and it's done, where it's like evolving all the time. And you need to keep all that content up.

>> Yep.

>> All the time.

>> Yeah. Just take an example of the role of technology. So how do companies provide ongoing training to the field? First, there's—

>> It varies very widely.

>> Yeah. The key is ongoing, right? It's not one-time. New-hire onboarding is one part, but how do you keep it current? How do you keep it continuous without overwhelming people? It's very common to see in companies that, okay, whenever there's a product release every other week, there's this Zoom meeting with a hundred people on it, saying that, "Hey, here's what we have built and here's what we are shipping." And half the people don't join, citing legit reasons—"I'm working on this deal" or whatever. And the people that join in, we don't know how—

Many are tuned in and how many are tuned out, and after the session is done, there's this recording sitting on Gong or a link is posted on Slack. A week later, there's a document that gets created—release notes—and that's it. Now, how do I take that and how do I update my product data sheets that have been circulating for a long time?

There comes the role of tech. There comes the role of AI. How do you do this kind of stuff? You know, a lot of times we look at AI as a much longer story. I've seen some of your perspectives on that. That's an interesting conversation that would be great to have. But I could leverage AI for some of this stuff. How do I keep content freshness? Content updates? These are solve problems, especially if you are able to get AI to be rooted in the source content. AI hallucinates. So you need systems and guardrails. Where if you were to constrain the problem statement saying that okay, here is your input. I don't want you to think too much. Just limit your answers based on what I'm giving you, and this is the specific job that I want you to do.

There are multiple things going on with this tech in terms of how do you do source grounding? For that, do I go to ChatGPT? Okay, yeah, I could do custom GPT or ChatGPT projects or I could do cloud projects or whatnot. But the hallucination problem doesn't go away. But if you were to go to something like Notebook LM, it does. But does it mean that I'm going to take my content, put it on Notebook LM, write some queries, then come and update my slide decks and PDFs? That's a lot of heavy lift. That's not going to happen, right? Can I have a more integrated system? This is where AI integrated into the workflow—systems workflows—right, wherein I could pull in a call recording, namely a product release webinar that was conducted internally. I extract the transcript and I would create a piece of content out of that—a summarization of that—and then I am able to identify the product content that needs to be updated.

You're getting into an agentic workflow that's connected and rooted in a business need, not just a buzzword, you know, to look cool for the investors or in the market. Talking about "I have got 200 agents." That's becoming like everybody's counting: "How many agents do I have?" So I have an agent for writing LinkedIn posts—that's an agent. I have an agent for writing an email—that's an agent. So everything is a content creation agent. You could call it one Uber agent, or people would count every little thing that their thing could do and call it like counting the number of agents.

There seems to be a race, especially in new companies that are emerging. People are talking about AI wrapper companies, if you will. Sure, you would be familiar with that. Put on a wrapper on top of an LLM—large language model—and I do ask trivial things of that and I would call each of them an agent.

Yeah, and it gets on it, right? But what I was referencing earlier is: how do I take these conversations? The conversation could be of a product release webinar, or I could take, okay, take all the discovery calls that have happened in the past month from Gong, take that content, and identify what are the common objections that have come up from across 20 customers. Can I do it at scale? And after you extract the objections, do I have my objection handling guides? Do they cover this? Is there a need for upleveling it? And that helps me in terms of keeping my content current. And this is far more possible today with AI than ever before. Earlier it was possible, but I needed to spend that time listening to those calls, parse that content, extract out the objections manually, and go on to update. Now that job is becoming much easier.

So you have to go through all the content, but one of the things that I've seen—and a little fun fact, Dale, I don't even think you know this—I actually spent call it six months in enablement. There's so much content, right? And this was obviously before AI could parse it, but there's so much content. How do you prioritize which content to use and which content to throw away? Said differently, how do you prioritize the context?

Great question. So it's very common to see, even with our customers, that a maximum of 10 to 15% of the content gets used by the reps. There's content pieces that get created that have never been seen in a year. But there is hesitation in terms of archiving there. There's this FOMO of okay, what happens if I delete? Maybe somebody will look at this content, right? And actually, it's becoming counterproductive. Where we actively advise our customers to retire content on a regular basis. Where we have AI—AI does provide the guidance. Instead of I could run a report to see which content was viewed last and engaged on, and so on. Now with AI, we are able to write a conversational query: "Show me all content over the past X number of days which has seen engagement and which did not see engagement," and connect it back with the questions that are coming up or the objections, and recommend the content that needs to be archived, right?

And more content—something that is necessary. Thank you for actually pointing it out. Having more content also results in another problem. It's almost like a garbage in, garbage out problem, right? So you have too much content. And there could be dated content that talks about the same stuff in different ways, and it is easy for the AI models to get confused in terms of which one should I pick the answers from.

Yeah, I like it. I mean, I think listen, AI makes it much easier than it ever was before. But having a way to systematically go through and figure out the contextual stuff and flag what isn't being used. And I think that's what was missing before, right? Is we have all of these million—I'm going through this with a client now, actually. I'm building onboarding for a new BDR. And the old sales leader is no longer here, and like there's no, like what are we using to onboard people? "Oh, I don't know." Well, how are you guys? I had a sales rep tell me the other day, "We don't have a sales deck." So I reach out to the marketing team. I'm like, "Why is there like, we have four different sales decks? They're in this folder. No one knows where the damn folder is."

So being able to actually see what is being used and what isn't, I think, is huge.

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So, you talk about the enablement of revenue gap. So let's talk a little bit about accountability and who should actually, like, how should enablement be tied to revenue?

Great question. So the classical measures have always been things around new hire onboarding, ramp time, time to first deal—those are common. But increasingly we're looking at this debate in enablement, pitching to the core here. But is enablement effectiveness measured in terms of causality or correlation? This is a forever ongoing debate. Does enablement cause the revenue outcome directly? Did I win this deal because of enablement? Or can I say that my enablement efforts are correlated with this person winning the deal or this team winning these deals or these revenue outcomes?

So there's a broader consensus in terms of like I could not clearly attribute or singularly attribute a revenue outcome—namely a closed one deal—just to training. Just because you took this training, you won the deal. Or just because you read this content or shared this content, that alone is going to be challenging, right?

Having said that, if we are able to elevate the role of enablement in terms of meeting the rep where they are at as they are working on a deal. The classic examples that resonate with our customers—some of the things that we do—is about the importance of social proof. Citing a relevant story from a relatable customer who has solved for the same pain point. All of us know this, but what are the reps doing today? They have these five or six case studies they have practiced with or they know, and that's what they keep sharing.

Now, can enablement surface the right customer story that takes into account the account's firmographics and stated problem statements, and with a similar person? Talked about that. If I share that both as a bite-sized content on a call like this and follow it up with a digital sales room that includes that piece of content, I'm taking a very simple example here, right? Just that power of telling the right story at the right moment to win over the buyer's confidence—that matters.

How do you think about it?

And I think if you can, first of all, I always believe that everyone across the go-to-market motion should be tying to revenue somehow, some place, because that's the only way to actually move the needle. Like time to first deal, time—like there's a lot of things that may happen on—

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That time to first deal could be territory, could be a lot of other things. But how do you actually get that lead into the funnel, qualify them properly, and start pushing them through the funnel with enablement content that you understand?

You probably need some tests or other things that you can run to make sure that enablement is being managed properly and they understand not only what we are delivering, but the why. I find we do a lot of what enablement, but we don't do a lot of why enablement. And if we don't do why enablement or people don't understand the why that they're doing something, they can never tell the story.

**Yes. Totally, totally, totally. Just extending on that, the effectiveness or the way to measure enablement—how well am I doing discovery calls? What are my micro conversions? Don't worry too much about the win rate, which is what every sales tech company out there talks about. We help you improve the win rate. We help you with quota attainment. We help you with closing the deal cycle. And all of that without running into that vanity—think about your micro conversions across the pipeline. How do you move from S1 to S2? What needs to happen in S1? What does a good discovery call look like where I can qualify in or qualify out?**

**Mm-hmm.**

**And how do I win the trust of the prospect that I'm talking to?**

**Mm-hmm. That aspect—you're getting into—okay, given that I know this person, how many people are doing the person research, going into LinkedIn and connecting back that person with the personal training that I might have received, personal objections that I have received? It's all part of my LMS, and there's a slide deck with 120 slides in it—all the personas that we sell to, four slides per persona. And there's this slide number four for every persona that lists out all the objections and pain points. Now, when I'm talking to this human being, am I going to remember slide number 63, which connects to this person? Am I remembering that?**

**What the tech is able to identify? You're meeting with this person. I know this person's title from your CRM and I know that that title maps to this persona, and here are the objections that come up. And I'm able to surface that. That's enablement delivering value.**

**Yep. 100%. And that's exactly what needs to happen—the value has to be delivered. Otherwise, there is no enablement. You have Google Drives and you have software and you have all sorts of things, but there's no value.**

So controversial question: in a modern go-to-market org, 2025 going into 2026, who owns enablement?

**That's a million-dollar question. I wish I had a magic wand. In terms of what I would recommend, I would recommend strongly that enablement reports into the CRO. CRO owns the budget, which is the case for most organizations. But then the CRO says that in a lot of companies, "I'm too busy to manage so many directs." So I would have enablement roll into RevOps. That's a trend that's coming up with a number of companies. Or the enablement doesn't get the mindshare. Technically, there might be a reporting relationship.**

**So the ideal structure—if I had the magic wand, I would say CRO spending 5% of her time on enablement, thinking about what enablement means. Not enablement, the function or the tools and all of that—what does the person, the leader, want the enablement to happen on? What do we need to enable that my team on? If that is clear to the team, the enablement professionals in the organization, the outcomes will be so much better.**

**Yeah, I couldn't agree more. I think for enablement to be viewed as important, as a real function, as a must, as a value, you have to have someone in the C-suite owning it, and it has to tie back to revenue. Otherwise, it's this afterthought that we have because we have to say we have an enablement team. But no one really cares about that.**

But sorry, just adding one more.

**No, go ahead please.**

**Yeah, please.**

**So what we are seeing in the market with our customers, again, is that the growing importance of customer success enablement. That's becoming a thing. Finally. The revenue enablement—the transition from sales enablement to revenue enablement. Initially, it was an analyst thing, but we are seeing that happen on the ground, right? So where a lot of expansion that we see has come from two areas: customer success enablement and from partner enablement. These are the two things that come up consistently.**

**And for customer success enablement, there are CS tools—Gainsight or any other alternatives that companies might choose. Those are more like operational tools for the customer success function. But how do I enable them on an ongoing basis? And the nature of enabling CS is different from the nature of enabling sellers. CS needs to be deeper in certain areas, could be more surface level—let's say on pricing or objections—but needs to be way deeper on the value prop and on product, because customers expect that, right?**

**So that specialization is starting to emerge right now. Users are getting added from the CS side, but CS enablement strategies are catching up. That's another trend that we are seeing.**

**And I would say a trend that I would love to see, and I think we've talked about this a long time in the go-to-market world, is all of the learnings that we're getting from the CS world get back into the marketing silos and the sales silos. Like, we don't have this full-loop conversation, because it's almost like it goes to CS and CS can tell you: do we really have an ICP? Like, we think we've qualified them in marketing and sales, but when we're doing the execution side of it and we're delivering the value that we promise in the sales world, is it the right person? Is it the right thing? Is the right messaging? Is it the why?**

**And then that message, that data flow, needs to go back into the marketing engine and the sales engine. And I have not seen anyone do this really well at all.**

**Yes. You have hit the nail on the head.**

**Don't give him credit, please, because I'll never hear the end of this. I hit the nail on the head for the first time ever. When was the last time you picked up a hammer, Dale, and actually hit anything?**

**A lot.**

**Probably more. Probably more recently than me, actually.**

**It's almost like such a temptation that you never want to say no to a deal that's closing.**

**It's so hard. Yeah.**

**And it gets into...**

**Especially now.**

**Yeah, yeah. Gets into the CS, and the team is throwing up their hands and saying, "Why did we even sign this with the promises of this stuff?" That's—no, it's been a problem for a while. It's not just new right now. The effects of that is becoming even more pronounced now because nobody wants to pass on a deal in this market.**

**Yeah.**

**Yeah. But not every deal is a good deal. Like, I...**

**I struggle with not wanting to pass on a deal. And listen, I'm guilty of it too. But like, you have to be able to look at a deal and be able to say, "Not a good deal."**

**Mm-hmm.**

**Or if it looks like a good deal and it is a good deal and you are going through it, but something is not working properly in the CS side. It could be product. It could be the promise of what we delivered. It could be a myriad of things. It could be shifting in the customer's business model. Like, that data needs to be fed back into the top of the funnel and throughout the whole funnel. Because if not, then we're just going to get into the cycle of: we're not getting the right people through the funnel. So our EBITDA and our gross margins are much lower than we need to be, and customers are costing us money.**

**So I haven't seen a full-loop cycle, a full-loop process, to get that data back into the right hands at the top of funnel.**

**Yeah.**

All right. Final question, and then we'll dig into some rapid fire. And this could be the first part of rapid fire, but I don't expect a super quick answer on this one.

It's two years from now. Enablement's changed over the years. We have a ton of AI. Onboarding has changed. Some companies do it great. Some companies do it like... where? What does enablement look like two years from now at a high level? What's a good enablement plan?

**A good enablement looks at equipping the reps as they're working on their deals with the right information, delivered at the right time, contextualized for the problem statement or the deal that they're working on. And this was always an expectation from the website. It's not a new expectation per se, but in two years from now, and in some areas already, it is possible that just-in-time enablement is not a theory anymore. It's not just marketing talk. There are elements of that that are already possible today. They'll get stronger in the next 12 months. I don't even think it requires 24 months for that.**

**Yes.**

All right, let's dive in. So the goal of rapid fire: 10 words or less. What's the one thing go-to-market teams are still doing that drives you nuts?

**Enablement. Doing it the wrong way.**

**I love that. Love that.**

**What's one piece of enablement advice**

That's a tough one. There are multiple perspectives to choose from. So I'd say there's still a world where people are insisting upon the badges, the importance of badges, learning paths, and stuff, where the world has changed quite a bit in terms of microlearning, byte-size learning, delivering in-the-moment learning. But there's a group of people who would still insist on their learning paths and courses and badges and so on.

>> That makes sense. Who's doing enablement right today?

>> Everybody in the company. In a good company, it starts with the CEO.

>> Let me reword it. I'm sorry. What company is doing enablement right today?

>> I would like to pass on the question.

>> Okay. I like that. I'll go to another one. This one's going to be just as controversial. If a rep fails, who's actually to blame?

>> First of all, I would say the rep himself or herself has at least a portion of the blame. If a person needs to be blamed, if I have—if you put a gun to my temple and say somebody has to be blamed—without sufficient information, I would say the rep has the ownership. If the rep needed support, they could have reached out internally.

>> Yeah, yeah, we can't be holding hands all the time. Last one as we wrap this up: What's your dream vacation destination, if you ever take a vacation?

>> Home with family. A long vacation with kids talking to me. I have two boys—they're 23 and 19 now. They don't spend a lot of time with parents, but my wonderful idea is staying home with them when they have time for me.

>> Awesome. I love that. By the way, as much as I travel—and Dale will make fun of me—I probably travel more than anyone I know. But there's something about just coming home and being home with my wife and my kid and sleeping in my own bed. As much as I love to travel, it's nice to be home.

>> Yep.

>> Shar, thank you so much for joining us and sharing your thoughts on all things enablement. Where can people learn more about what you're up to, and where can people learn more about GTMBuddy?

>> So we're at gtmbuddy.ai, which is our website, and I'm on LinkedIn: Sriraini.

>> Everyone's on LinkedIn. We're all on LinkedIn. Awesome. Thank you so much for joining the show.

>> Thank you so much for having me. Wonderful speaking with you. Thank you.