Episode #105 Enablement Is DEAD: Why Sales Teams Don’t Trust You Anymore with Sreedhar Peddineni

Sales enablement sounds great on paper. In practice? It’s a mess.

In this episode of Bridge the Gap, we sit down with Sreedhar Peddineni, founder of GTM Buddy and co-creator of Gainsight, to pull apart everything wrong with enablement in modern GTM orgs — and how to fix it.

From outdated content and AI hype to onboarding disasters and leadership blind spots, Shridhar holds nothing back. If you’re in sales, marketing, enablement, RevOps — or just tired of pretending like enablement isn’t a mess — this one’s for you.

🚨 Topics We Cover:
•Why enablement gets cut first — and what that reveals
•What “just-in-time enablement” should actually look like
•Why your team hates your onboarding (and they’re right)
•How to tie enablement to revenue without lying to yourself
•The biggest mistakes GTM leaders still make in 2025

Follow Sreedhar - https://www.linkedin.com/in/sreedharpeddineni

PS - huge shout out to Sendoso for sponsoring our show.

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ZoomInfo is also a proud sponsor - check them out here!

🎁 Lastly, we have a gift for you! We’re tired of seeing people getting critical GTM components wrong. Need help with your ICP, Buyer Persona, and Value Prop? Tired of the shitty “resources” people “give away” to gain followers?

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Transcript

This is Bridge the Gap powered by Revenue Reimagined, the podcast where we dive into all things revenue. Each episode, we bring you the top founders and go-to-market leaders to challenge how you think about growth and help you bridge your biggest go-to-market gaps. I'm Adam Jay. And I'm Dale Zwizinski. 

As always, thanks for hanging with us. There's a million ways you can be spending your time and we're grateful for you choosing to spend it with us. Be sure to check out our newsletter if you want the show notes and tactical advice on how to bridge your GTM Gaps. Let's get to it. 

Welcome back to another episode of the Bridge the Gap podcast powered by none other than Revenue Reimagined. Today's guest is Shradheer Panini, who is the founder of GTM Buddy and one of the original co-founders of Gainsight, where he helped get this, 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. Shradheer, thanks for joining the show. Thank you for having me. 

Awesome. Let's get, like, jump right into it. So enable it as it exists is kind of a joke. Like, 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's that, where does it start? Why is it so broken? 

Yeah, it's really interesting one. So, like, you have been in leadership roles for most of the past 25 years. And whenever we are having conversations at the leadership level, we'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. The new competitors coming up. 

The market is changing, and we need to up-level our teams on a continuous basis. I've never, ever come across any leaders in my personal experiences and in my network. Anybody who questions this fundamental premise that enablement is important. Right? But at the same time, we are seeing this, especially with the end of growth at all cost mindset over the past few years, a lot of enablement professionals, seasoned professionals, a lot of well-respected enablement professionals have been impacted by it, by the layoffs and so on. Now, what gives? Why, what's happening here? There's a lot of perspective that we hear that, okay, enablement is good to have. When the times are hard, you've got good to have. It's a cost center. 

I'm sorry to interrupt you, but you hit a nail in the head. I worked for Toast for many, 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. Wow. That's a massive cut. Don't need enablement anymore. Times are tough, so you don't need to train your people? Yep. 

And a lot of times, people think that, at least, a lot of enablers come with an enablement background, and there's a lot of excessive focus in many ways in terms of new hire onboarding, ramp time, a lot of that gets talked about. And when in the world where nobody is hiring a lot, then 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 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 some geeky people who are doing this cool stuff with this tool, chat equity or cloud or things like that, but a vast majority of people are going into chat equity and they're using it like Google search. Yeah. There's this interesting statistic that we see in our own platform. We have a chat equity style UI where reps can ask questions and define answers. That's within GTM body platform. And we get access to the statistics and also how the people use the tool. The most common length of a prompt is about pre-words. Yeah. 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 it's like when we do the evaluation and we may need to find additional teammates or we may need to level people up. There's no enablement. And like that list 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. 

Like here's your badge, here's your laptop, here's your blog. But they don't do go to market onboarding. And you're spending a lot of money on these people. And we talk about the cost on a phone 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 extending on that observation days. 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 really seems to be how we are enabling people. The leadership does not seem to be convinced that the way we are enabling the team is the problem. And some people get ascribed to the people who are doing the function, whether or not they have the charter or 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 how, I was reading your content, you talk about the gap. 

And I believe that gap is in terms of the expectations versus the reality. Most enablement come on board. Like you said, one of the first things that you do, you do company on board. 

Yes, you do it with new highs. This is our company and our culture, this is the history and this is the employee policies and all of that. That's all needed, fine. 

But what's 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, okay. 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, might make minor tweaks and so on. But when the change is coming at a box speed, the domain is evolving, the product is evolving and the competition is evolving. How do you take correct? To begin with, are the enablers enabled to keep pace with the change that's hitting them? 

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

I think, hate to say this, but I guess my perspective is that all three of them, right? And that's okay. Yeah, so when you look at the people aspect of it, first and first, enablement needs to feel supported and empowered to begin with. 

That's the two ways to do it. And in order to give that trust and empowerment, the leaders needs to be convinced that there's a strong 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. The people empowerment, empowerment gap. 

That's one issue. And the second issue is about the currentness or how current is the enablement content that I'm creating. Call it learning content, data sheets or comp intel 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 into their laptops, they would tweak it a little, make it their own. They'll keep using it. 

And there's no coming back after that, right? So if you want to keep the content current, now you move into the technology problem. I could throw bodies at keeping the information current at all times. Most companies operate on a biweekly sprint. If you talk about product knowledge being current. Companies operate on a biweekly sprint and tag, 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. How do people... 

And enablement and training. The challenge is people think it's a one-time thing in the stun where it's like evolving all the time and you need to keep all that content up all the time. 

Yeah, just taking an example of the role of technology. So how do companies provide ongoing training to the field? Because there's the... 

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 is very, very common to see in companies that whenever there's a product release, every other week, there's this Zoom meeting with 100 people on it. Saying that, hey, here is what we have best and here is what we are shipping. And half the people don't join. 

Legit reasons I'm working on this deal or whatever. And the people that join, 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 on sitting on GONE or a link is posted on Slack. A week later, there's a document that gets created or 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? Therein comes the role of tech. Therein comes the role of AI. 

How do you do this kind of stuff? So a lot of times we look at, AI is a much longer story. I've seen some of your perspective on that. 

That's an interesting conversation that would be great to have. But I could leverage AI for some of this stuff, whereas how do I keep content freshness, content updates? These are solved problems, especially if you're 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 that are going on. There's tech in terms of how do you do source content. And for that, do I go to ChargeGPT? 

Okay, yeah, I could do custom GPT or ChargeGPT projects or do cloud projects or whatnot. But halization doesn't go away. But if you were to go to something like a notebook LN, it does. But does it mean that I'm going to take my content, put it on notebook LN, write some queries, then comment, update my slide decks and PDFs back? 

That's a lot of things. Not going to happen. Can I have a more integrated system? This is where AI integrated into the workflow system, workflows. 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 are getting into an agent workflow that's connected and put it in a business need. 

Not just a buzzword of, you know, to look cool for the investors or in the market. Talking about I have got a 200 agents that's becoming like everybody's counting how many agents do I have. So I have an agent for writing LinkedIn post. 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 calling it like counting the number of agents. There seems to be a raise, especially in the new companies that are emerging companies. People are talking about AI, Rapper 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 our severe things of that. And I would call each of them an agent. Yeah. 

And it gets onto it. But what I was referencing earlier is that how do I take this conversation? The conversation could be of a product that is enough or I could take. 

Okay. Take all the discovery calls that have happened in the past month from GOM. 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 I extract the objections, do I have my objection handling rights? Do they cover it? Is there a need for up leveling 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, pass that content, extract out the objections manually and go on to update. Now that job is becoming much more easier now. 

So you have to go through all the content. But one of the things that I've seen in little fun fact, Dale, I don't even think you know this. I actually spent, call it six months in enablement. Is there 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, very common to see even with our customers that a maximum of 10 to 15% of the content gets used by the app. There's content pieces that get created that have never been seen in a year. But there is hesitation in terms of archiving that there is this FOMO of, okay, what happens if I delete? 

Maybe somebody will look at this content. And actually it's becoming counterproductive where we actively advise our customers to retire content on a regular basis. Where we have, AI does provide the guidance in terms of, in so I could run a report to see which content was viewed the last and engaged and so on. 

Now with AI we are able to write a conversational peri-shoming all content over the past X number of days which has seen engagement, 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. And the more content, that's something that is necessary. 

Thank you for actually pointing it out. And having more content also results in another problem. It's almost like a garbage in garbage out problem. So you have too much content and there could be dated content that talks about the same stuff in different way. 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? All of these million, I'm going through this with a client now, actually. I'm building onboarding for a new BBR. And the old sales leaders no longer here. And 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 reached 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 it's huge. People buy from people. That's why companies who invest in meaningful connections win. The best part, gifting doesn't have to be expensive to drive results. Just thoughtful. Sundosa's intelligent gifting platform is designed to boost personalized engagement throughout the entire sales process. Trust me, I let sales first Sundosa competitor and I could tell you, no one does gifting better than Sundosa. If you're looking for a proven way to win and retain more customers, visit sundosa.com. 

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 missions have always been things that are new hire, onboarding, exam time, time to first deal. That's those are common. But increasingly we are looking at the, this debate in enablement, which is to the core here, but is this enablement effectiveness, is it 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 the revenue outcomes? So this broader consensus in terms of like, I could not clearly attribute or singularly attribute a revenue outcome, namely a close 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 won the deal, is going to be challenging. 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 getting working on it, the classic examples that resonate with our customers, some of things that we do is what we all know about the importance of social growth. Citing an 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 this five or six case studies they have practiced with or they know, and that's what they keep sharing. Now, if enablement is able to surface the right customer story that takes into account the accounts, thermographics and stated problem statements, and where the 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 system that includes that piece of content. I'm taking a very simple example here. Just that power of telling the right story at the right moment to win over the bias content, that message. 

First of all, I always believe that everyone across the go-to-market motion should be tying to revenue at some place because that's the only way to actually move the needle. Time the first deal, there's a lot of things that may happen on the time the 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? And 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 work enablement, but we don't do a lot of why enablement. And so 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 of 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 tech company out there talks about. We help you improve the win rate, we help you with quota attainment, we help you with crashing 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? And how do I win the trust of the prospect that I'm talking to? 

That aspect, you're getting into, okay, given that I know this person, how many people are doing the other person research, going into LinkedIn and connecting back that person with the person or 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 stuff that we sell to four slides per person. 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 this slide number 63, which connects to this person? 

Am I remembering that? 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 suggest that. That's enablement delivering value. 

Yep, 100%. 

And that's exactly what needs to happen is that 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. Modern go to market org, 2025 going into 2026. Who owns enablement? 

That's a million dollar question. I wish I had a magic bond. I know what I would recommend. I would recommend that strongly that enablement reports into the CRO. CRO owns the budget, which is the case with most organizations. But then CRO says that in a lot of companies that I'm too busy and to manage so many directs. So I would have enablement rolling to revops. That's a trend that's coming up with a number of companies. Or the enablement doesn't get the mind share. 

Technically, they might be a recording relationship. So the idea is that 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 wants? If that is clear to the team, the enablement professionals in the organization, the outcomes would be so much more better. 

Yeah, I couldn't agree more. I think you need 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. 

Sorry, just adding one. No, go ahead, please. Yeah, please. So what you're seeing in the market with our customers 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. So with a lot of explanations that we see have 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, the insight or any other alternatives that the 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 seller. CS needs to be deeper in certain areas, could be more surface level, it's on pricing or objection, but needs to be way deeper on the value prop and on product, because customers expect that. 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. 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? 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 it 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 problem on its nail on its head. 

Don't give him credit, please, because I'll never hear the end of it. 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? Probably more recently than me, actually. 

So it was like such a temptation that you never want to say no to your dealer's closing. Yeah, so hard. And it gets into the CS and the team throws it throwing up their hands and saying, why did we even sign this with the promises of this task? 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 put on a diss in this market. 

Yeah, but not every deal is a good deal. I struggle with not wanting to pass on a deal. And listen, I'm guilty of it too, but you have to be able to look at a deal and be able to say not a good deal. 

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. 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. 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 going to get 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 process to get that data back into the right hands at the top of the funnel. Let's take it. 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 has changed over the years. We have a ton of AI. Onboarding has changed. Some companies do it great. 

Some companies do it like shit. 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 deals 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 the just in time enablement is not a theory anymore. It's not just the 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, do you get the wrong way? 

Love that. Love that. What's one piece of enablement advice that you completely agree with, you completely disagree with right now? 

That's the one, the multiple to choose from. So I'd say there's still a world where people insisting upon the badges, the importance of badges, learning paths and stuff, where the world has changed quite a bit in terms of micro learning, bite size learning, delivering the 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, he starts with the CEO. 

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

I would like to pause on the question. 

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

What's the point, I would say the rep himself or herself? At least a portion of the blame. If a person needs to be blamed, if I have, you put a gun on my temple and say, somebody has to be. Without sufficient information, I would say that, okay, the rep has the ownership. If the rep needed support could have reached out internally. Yeah. 

We can't be holding hands all the time. Last one is we're out to talk. 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 to grow boys like that, 23 and 19 now. They don't spend, they don't have a lot of time for parents. But my idea is staying home with them and they have time for me. 

I love that, by the way. As much as I travel and Dale will make fun of me, I travel probably more than anyone I know. There's something about just coming home and being home with my wife and my kid and sleeping in my own bed. That is much as I love to travel and like, man, it's nice to be home. 

Yep. Shridhar, thank you so much for joining us, 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 GTM buddies? 

So we're at gtmbuddy.ai, it's our website. And I'm on LinkedIn, Shridhar Pardineni. 

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

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

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