Most Sales Enablement Teams Are Failing- Here's Why? | Ruchi Saini

Most sales teams do not have a coaching problem. They have a diagnosis problem. They're training the wrong reps on the wrong thing at the wrong time. And by the time they realize it, the deal is gone. In this episode, Ruchi Sani, one of the sharpest minds in SaaS. Enablement reveals the brutal truth. Enablement is not just broken, it's decades behind. You learn how AI powered role plays are replacing ride alongs, how real time insights are replacing end of corporate reviews, and why the best reps are skipping enablement entirely, building their own systems. And this is not another best practices chat, it's a survival guide. Because if you're still reacting after the fire started, you won't make it to the next quarter. Ranchi, you've seen this transformation up close. What is the biggest wake up call sales enablement leaders need to hear right now?

I think the biggest wake up call that sales enablement leaders need to hear right now is your enabling approach. And your coaching cannot be ad hoc, reactive, observational, based on guesswork anymore. It has to be personalized, it has to be predictive, it has to be proactive. And you will have to embrace artificial intelligence. It's not the future, it's present, it's already here. Think of it as an agent that's there with you 24 7, never takes a coffee break, never asks for a leave, it's always helping you. And it's certainly going to help us elevate the way our function is perceived in the industry. And it's going to help us make that needle movement from being looked at as a cost center to actually a strategic function that's helping solve larger problems for companies out there. And if we are still relying on traditional methods where we are waiting for problems to occur so that we can figure out what should enablement do now, then we're definitely lagging behind.

Love that. And that makes so much sense. You know, enablement has shifted from being a reactive support function to a strategic performance driver. Let's unpack that a little. Okay, so if enablement was seen as more of a support role five years ago, what is it expected to deliver today? If it was on the phone even.

Now, if you approach people and you ask them, hey, you're starting an enablement team or you're hiring an enablement rep in your organization, what is expected out of them? People will tell you, we have new people joining in, we need them to do onboarding, we need our people ramped up faster and so on. So I think it's got a lot to do with that mindset change that's happening across the board where we're actively involved in deal discussions, forecast discussions, reviews, QVRs. We have visibility into the pipeline not just in terms of the numbers, but the entire sales journey of a deal throughout the sales cycle so that we can identify gaps and provide help right then and there where the seller needs it, instead of providing generic coaching sessions where nobody really learns a lot and they don't go back and implement that in their actual workflow.

You mentioned earlier that, you know, sales enablement is still too reactive. And I can agree. I see that all the time, too. What do you think is one thing that most teams are doing too late that they should be doing much earlier?

I think we wait for people to come to us with problems and then we think of a process that we can put in place to solve those problems instead of us identifying gaps, or I'd rather say foreseeable gaps that can occur at any point of time during the sales journey and provide a solution to it so that the seller, the sales deal, the execution doesn't suffer. So similar to what you said, we're just sitting here, we are creating a lot of content. Our calendars look busy, we're doing tons of trainings, but we don't know where that's heading, what's the impact of it on the business. And then we wait for business to come to us and say, hey, our win rates are down, can you do something about it? And then we're constantly thinking on our feet, firefighting, solving a lot of problems and not attaining that level of efficacy with each approach because it's very, very ad hoc and reactive.

Got it. And it's clear, you know, the expectation from sales enablement has changed. Like you mentioned and you mentioned earlier, one of the biggest reason for that shift is also AI. And I'm aligned with when you said, you know, how, you know, companies think of this as reactive approach even today. And while a lot of people are talking about AI, I don't think so. Everyone is using it. Well, I might be aware of some use cases that say in sales, in general, prospecting, closing, I had no idea about. So in your experience, where is AI actually helping your teams enablement teams be dangerous?

Not just as I think AI is a very, very powerful tool and I firmly believe in that because we are experimenting left, right and center with AI technologies out there. I feel like for every problem out there, there's an AI tool that exists. And some of the areas where we have tested different use cases for AI and it's proven to be a massive game changer for us would be one in terms of content creation, not just for the enablement team, but for the product marketing team, for the LND teams out there as well. You don't have to spend hours and hours creating content, then proofreading that content and then that content coming back to you. You having to create several iterations of it for several different kinds of audience. All those manners gone and very little outcome achieved out of it. You can do that with any AI tool out there, the good ones of course, in fraction of minutes. And we've seen some beautiful results coming out of those content creation AI tools that we've experimented with off late. Apart from that, conversational intelligence has been again a massive game changer in the last few years. I don't think people really had that mindset of thinking beyond a call getting recorded. But now you can pick up key moments, keywords, longest monologue. And based on the conversation, the tool is also highlighting where are the risks in the deals, what's missing, what you could have done better. All that intelligence was not there and it's really helping us, not just the seller, but also the managers and picking up those data points because it's taking the guesswork out of everyone's work. It's not observational anymore. Everything's there in black and white. It's reducing a lot of admin work for you as well as an enablement person or even for our partners in Revops because there's tons of data. It's filtering out that data for you and giving you actionable insights. And one area where I've seen a massive, massive change is AI powered roleplays. Super, super important because you have so many reps, you can't be everywhere help every rep on every call. So they need some kind of safe space with psychological safety where they can practice before their actual sales call, get that actionable feedback that they can implement without feeling like they've been put on the spot or they're getting to learn from someone who probably does not know as much as they do if they haven't done sales before. So there are a lot of inhibitions as well when you work with different sellers. I have seen that AI powered role plays have proven to be really helpful. No amount of ever boarding can help you provide that one is to one customized personalized coaching to each rep in your team right when they need it. If I have a pricing call tomorrow, I don't want to wait for my enabler to find time on her calendar to sit with me and then for us to figure out how should this conversation go tomorrow so that my opportunity, which is bottom of the funnel now I don't lose it. Eventually I can just use the beautiful tools out there. I can use one of those AI tools in my comfortable space. The tool is also going to tell me what are the kind of questions you could have asked, you know, what did you miss out on asking? What are the things that you did really well? Here are some of the things that you should know about this customer etc etc. And now I'm well prepared and it takes away a lot of dependency as well of sellers on their managers and their enablers. So that's one area where I've seen it to be really effective in driving real outcomes for us and on all fronts, not just the sellers or the AE side of the business. But even with our HDR ecosystem, it's proven to be really helpful.

Wow. You know, that's a lot to unpack. So you mentioned content creation, call coaching and personalization. I want to play very quick game. If you could only keep one call coaching, content creation or personalized training, which one are you fighting to keep in mind?

Coaching 100%.

Okay. Do you want to explain why?

Because the expectation from you as an enablement team is that you're going to help people do better at their jobs. That's what we're supposed to do. And that's not going to come from giving them hundreds of pieces of text and videos to go through. That's not going to come from us conducting hundreds of sessions out there. People need that help. And the only way you can help people is if you know the needs are very nuanced. Someone's new in the system, someone's old in the system, someone's good at prospecting, someone's good at. Objection. Handling. Someone's good. The negotiation. Everybody has different needs and they need that kind of personalized coaching in that regards. So if I'm somebody who's very good at pipegen, but for some reason I'm not a good closer, I don't want to sit through a session on discovery because it's not helping me. So everybody has very nuanced needs and like I said, an enabler cannot be in hundred different places at once. You cannot have an army of enablers working with different sellers. So that's where AI is going to be super, super powerful and impactful. That would be one area that I would pick. Coaching. 100% Interesting.

I like that insight. Let's flip that for a minute. Okay, what's one use case AI use case that you think is a total waste of time right now? Or at least let's double click on something which you have brought up time and again, which is AI powered coaching. Because coaching has always been one of the things that's high value but hard to scale. So here's the real question. Does AI actually make reps better or do you think it's just another shiny tool? I know you endorsed this a bit already, but I want to still go deep into this and understand your I.

Have firsthand seen massive improvements in some of the BDRs whom we recruited. They were fresh out of college, they had no sales experience, but they needed to be ramped up in maximum six weeks to go live into production and they were doing mocks with us, with their buddies. But we knew that's not going to help us move the needle. And our usage of AI to complement what we were doing and provide that relevant support to them has helped them meet their targets as soon as the event lies. Soft quarter with the company where I am at, what fix, they've all been able to meet their targets.

I love that and especially the idea of AI picking up talk time objection moments that a manager even might miss at the same time, like you said, how it has helped your entire team ramp up faster. Have you seen any other insights from AI that probably surprised you? Something, let's say even a great human coach like you and me might have.

Missed plenty actually, and in different areas. So in terms of call prep prior to a call, as an enabler, you will not always have visibility into every lead, every opportunity that someone is working in. And so your feedback is purely going to be based that one conversation that you have with that person. What AI tools do these days is they integrate with the CRMs out there. They're integrating with several other tools in your tech stack to provide you with a comprehensive feedback. This is what I know about your deal so far basis the notes that you've entered in Salesforce. These are the things which are currently missing and on your next conversation these are the things that you should be saying. It's not manually possible to do that for every deal, every opportunity out there. So those kind of insights have been have been super helpful. We've used tools where you get this entire report that gets emailed to the seller or the XDR right afterwards and it has everything what was your language like? What was your level of proficiency? What were the questions that stood out and what were the questions which should be eliminated and you shouldn't be asking them because they're risky. And here are some of the words which are too high risk to be utilized in this conversation. Keeping the nature of your prospect that you've mentioned and here are some of the powerful words that you should be utilizing. So lots of things which we when we give subjective feedback, it's purely basis that one conversation, that one mock that we've done with the person and detached from the actual opportunity that they're working on.

I want to flip the lens a bit and I love the insight that you mentioned this, but I'm also thinking from a SDR lens right now. If I'm an SDR listening to you, maybe I don't have a lot of 101 coaching. And let's face it, not every company is as good as what makes. But I do have access to ChatGPT. I have access to, let's say, some call summaries or gong summaries or even call feedback. How can I as a rep use the AI to coach myself even without informal.

That's actually a good question. There are some of the ways where before we started testing out the AI tools out there where we used to coach our teams some of those areas. For example, when it comes to prospecting and you have to send emails, we would enable our BDRs with. Here are some of the prompts that work. Go ahead, utilize these. Here's a bad email. We want you to turn this into a highly personalized, effective prospecting email that you would send to this particular prospect and then come back and then we would discuss more prompts. So we've seen tag being used left, right and center. I use it every day for lots of work that I do. That's one of the ways we've even seen people come up with, you know, not every BDR wants to just wing it. Some people like to have some kind of script which they just want to keep there as a plan B. They've been able to come up with some really good elevator pitches. We've been able to secure a lot of good responses to some of the objections that we get on the calls. And I even use that as an enabler. Sometimes I'd go to ChatGPT and I would say, this is an objection that we get from our customers. This is a response that I can think of. Do you have anything better that you can share with me? And then I'll get several suggestions and sometimes they resonate with you and help you refine the quality of content that you're creating for your people.

Amazing.

I don't know if that helps.

No, it does. See, I think, I think I'm totally aligned with you. I don't even have the count of the number of hours I spend with ChatGPT. Yeah, I have the like the Pro Pro version, like $200 a month version. So I do like deep, deep research. And even, even while preparing for the podcast, I think I did that not just with you, but I think for all the podcasts for a lot of things, which we do. We are preparing right now the next curriculum for school of sdr and we've done like deep research combining and going to the depth of things which we don't even remember, you know, which was taken from three years ago. How things have changed.

Yeah.

And it's impossible to keep up. Right. And as a human, I can only keep up with so much. So I think that's where I believe AI kind of gives me the sanity. And I think there are ways I can't even disclose publicly how I use it all ethically. But you know, you, you, you'll be surprised and you'll be like, wow, you know, for this as well, you're using Chat gpd. But the truth is, yes, we're kind of so much dependent on it. Go to personal, you know, habit of using chat GPD is when I go to the gym, it's a 10 minute walk and I switch on the voice mode and I'm talking random things and saying, hey, give me the structure, give me a thought process. I believe I'm not structuring it right. I'm not thinking it right. And between, in the gym, when I'm, you know, between the sets taking rest, that's when I'm again chatting with ChatGPT. So that's how I think. Sometimes it scares me that I'm probably in the, in the phase where it's actually becoming that whole thing where I'm probably getting in love with AI.

Yeah. Yeah.

So yeah, it's scary and at the same time exciting at the same time. I'm kind of loving it. Anyway, I think we talked about AI coaching so much. I wanted to also talk about other companies were also exploring AI driven coaching. What is one common mistake which you feel enablement teams might make or are making when implementing AI?

If you don't know what's the goal that you're chasing or what's the outcome that's anticipated out of any process being laid out, then you just firing shots in random directions and hoping that one of Them hits, you know what I mean? So, and then we need to solve, we need to have a very problem solving approach. So what are your key problems at the moment that you're looking to solve for the company, not for your team. You need to keep the larger company okrs and problems in mind. And whatever tool you're evaluating amongst those high priority problems, how many of these is it able to solve for you? Because there are tons of tools out there. Like I told you, for every problem there's a tool out there. Even in the whole arena of call coaching, there are several tools out there. How many of them are aligned with the business objectives that you're looking to meet? What's the goal that's anticipated? What does your success criteria look like? And how successfully can this company partner with you before you even make that decision? And once you roll it out, it cannot be a one size fits all. And you need to keep in mind the nuances associated with different kinds of audiences that you have at the maturity levels. BTRs would have different needs, your A's would probably have different needs. So how you're gonna still customize this? The usage of this tool for different teams is important because it cannot be one size fits all. So if you just roll it out, glorify it and say, hey, we've invested in this tool and we need you all to start using it, that's not gonna cut it. And months down the line, if you don't know where you were and how far along are you in terms of a metric that you were chasing, whether it's win rate, conversions, your sales velocity, pipe gen, whatever it is that you're tracking, if you're not doing that, then it's just you're adding one more tool in that tech stack to an already heavy tech stack that your seller has to use. And you'll receive that feedback from them where you've just added to their list of laundry activities and given them very less time to sell, which is their biggest complaint with enablement and our function, you know, in general where they need more time to sell and we need to think along the lines of how can we make their lives easier, how can we make them more productive, how can we automate tasks for them? So we need to think of sellers needs, but also tied to the larger business metrics that we are looking at. Otherwise, one year down the line, if that tool hasn't made any movement in terms of the business metrics that you were tracking, then your entire project was a fail and you end up looking bad. Within the company.

So Ruchi, we talked about what's working right now. I want to talk about the future because I know that you're already thinking five steps ahead. What do you think is one AI capability you think is coming next in enablement? That most people would be excited.

It's going to be long term, Rahul. But I think that what the future possibly might look like would be an AI agent being there with you at all times. Because your enabler can't be your manager, can't be. On every deal and every conversation that you have, there's someone who's telling you they don't ask this question. Your next question should be along these lines. This is what you should tell this customer now to provide them value. Here are the weak spots in the conversation. Or be able to figure out and pick up non verbal cues from the customer and say, hey Rahul, read the room. The customer seems to be disinterested. Can you just quickly engage them with this question? Something along those lines would be really, really helpful. But I can also understand the apprehension because a lot of leaders might feel like isn't that my job?

No, I mean I'm thinking if I were to put a same leader hat right now and let's say you are my prospect, right? And not everybody is, you know, smart enough where they have the social quotient or emotional quotient, where they're able to read faces, you know, read minute nuances. So if AI is able to tell me, hey, Ruchi doesn't seem interested. Like you mentioned earlier, AI is able, if AI is able to detect where the call is going off, where the call is going off track. If similarly in a demo, if I'm able to prevent that real time because what we discussed earlier was course call, right? Oh, here is where you went wrong. But if I'm able to course correct, like right now, why would I leave that opportunity?

Yeah, yeah, I have, I have heard conversations where prospects have. When we ask them, how are you? How's your day going? And the prospect is not so good. And we dive deep diving straight into the agenda and we're saying, okay, this is what the call is going to look like. Ask the guy what happened? Is this a bad time? Do we need to reschedule? I understand little bit of empathy and I feel okay. It's easier for us as enablers to say that because probably it comes to us naturally because we're in that rhythm of coaching people all the time. But when you're on that call sometimes it doesn't Occur to you. Everybody is at a different level of proficiency. And again, that's why everybody has nuanced needs. But that's definitely the future for sure.

Yeah. I'll tell you what. We explored a tool last year for school of SDR where what it does is, if I have 20 students in the class, it can detect who is actually watching the screen and who has checked it to do something else. On a sidebar, it tells me who the engagement score of each person, and that's based on how frequently they're switching screens. So it doesn't tell me what they're looking at. It simply tells me if I Are they on the screen I'm presenting or are they looking at the zoom or are they looking at something else?

Yeah.

Imagine if we were to be able to do that real time. And that helps me. I mean, we don't have the tool. I'm just saying if we did. I think if I see how Ruchi is probably engaged somewhere else and I can probably call out, Richie, hey, Ruchi.

What do you think?

All of a sudden Ruchi is like, oh, my God, you know, my name has been called out and this can happen more, more often. So I would rather pay attention rather than, you know, doing something else.

Yeah. Several other use cases, like, you know, for example, you have multiple people on the call and you're constantly asking all your questions and directing them towards one or two person. And there's a third person who's just quiet throughout the entire conversation. And it probably doesn't occur to you at times as well, but that slight nudge where it tells you, hello, you have someone from the IT team. They're an important stakeholder. The risk assessment will happen there. Good time to engage them because they don't usually get involved early in the opportunities. This is what's the trend we've seen that would help you, you know, prevent that conversation from going south and rescue it before there's a massive.

I can think of so many use cases. So let's say Ruchi returned from a holiday and imagine I don't know how to start a conversation. Ruchi hasn't been speaking for a while, but I have a conversation starter, you know, popped up on in my screen where it says, hey, ask Ruchi about the London vacation. You know, has she returned? Is she still there? You know, that could be a good starter and it'll be great for people that say, who do not know how to start.

Yeah, yeah. One of the areas where we also implemented AI for our XDR teams was we have some of our key competitors. The moment that competitor's name comes up in a conversation, immediately a battle card will open up for you with the top three pointers relevant to that person whom you're speaking with. So now you don't have to think of, okay, these are several reasons where we win what would be most relevant for this person. And I don't have to recall all those CI metrics or areas where we do better than our competitors on the go, because those Persona cards, those battle cards are popping up for us right there in the conversation. That's proven to be really helpful as well.

See, I believe that's slightly also getting old because one, you as let's say head of sales enablement, has to still go and punch those battle cards.

Yep.

The way the future we are imagining right now is if there are three people who have already dealt with all that competitor questions right in the company. So instead of enablement team, let's say working with the sale leader on how to best pitch. We already know what has worked. Why don't we take those insights, put it in real time and say, hey, your colleague closed a deal sometime back with this fetch. Why don't you try this? Yeah, 100% that will that, will that. I think that will be the future.

Yeah. And let's up level that a bit. Pricing conversations. Huge dependency of sellers on their managers. Right. Every pricing discussion, you need your manager to be there and they only have limited bandwidth. But now if you have a frame of reference where somebody says, in this particular industry, these are the kind of deals that have closed and these were the areas where we went above the list price. So go ahead, don't worry, don't be hesitant, and go ahead and quote this price. That's the kind of help people need because they're often wondering, should I give a massive discount or should I quote above the list price? Below the list price. Oh, this is so complicated. I don't want to lose my deal. Let me just put all that pressure on my manager, have him drive that conversation. So several areas where it's also going to reduce the dependency of the sellers, make them more independent, more confident in their approach towards sales overall, and make them future ready.

Interesting. Yeah, I think I love the conversation so far. Ruchi, I have a final question for you. Okay. Now you have to imagine that you have got to fire your entire tech stack, which you have right now, rebuild everything from scratch. What will make the cut and what role would AI play from day one.

If I'm building everything from scratch, I. And when you say I'm building everything from scratch, does that mean I'm also doing away with all the content that we have? Everything. Everything. Okay. I would need to have one tool that helps with the productivity of my team. We don't want to waste a lot of. Waste is a wrong, negative word to use. But we don't want to spend a lot of hours creating tons and tons of content where we're going to again face the issue of adoption with the seller. So we want to create content that clicks and helps them. So I would want to use some kind of tool that helps us automate that task and create powerful content that can be delivered and can. And the adoption of it, the effectiveness of it can also be tracked. That would be one second would be having a call coaching AI tool in place that helps prior to the call, during the call and post the call. If that can be done with one tool, nothing like it. If I need to do that with the combination of tool where I need to have gong or chorus or call AI partner with another tool out there like blue or work ramp or hyperbound, then I do that. And the last one would be a tool like go Astra or docket out there, which would help us with predictive de coaching. Instead of us wondering where are all our deals going or forecasting being going for a toss rescuing before they see failure, identifying gaps in them and also reducing a lot of admin work for the sellers. That's another thing that we would want to do so that sellers don't see places like CRM as a place where I'm putting in a lot of information, but there's nothing in it for me. How can we automate that for them so that they have more time to sell? So I'd invest in any tool that helps make those redundant, monotonous, repetitive tasks, take those away from a seller, automate those and help us with predictive coaching. Give us real insights into the deals where it's heading so that we can take proactive measures during the deal cycle and partner with the sellers and ensure that the deal goes to closure.

Amazing. Thank you so much. Now we're walking into the last part of the podcast. Okay. You have no idea about what's going to happen. This is where we wrap with the rapid fire. You have to ask first answer that comes to your mind. Let me know when you're ready.

I don't do well with rapid fire, but I'll try.

Okay, question number one, wrong answer only. Okay. What is the best way to say rap think like a RAP1 sales enablement buzzword you wish you would, you know, you wish would die in 2025.

Training. I don't want to hear that word again ever again in my life.

See, you're doing well. Only three more questions left. If AI would coach like a celebrity, you know, Oprah or Gordon Brownstone.

I'm already a fan of everything that I know or hear about.

When you want to take care of people, you're like, oh, my God, you know, I want to take care of everybody.

Uplift the world. Use AI in good hands is a very powerful technology. AI in bad hands. Well, you know, I definitely want opera to leverage it. Yeah. And help people around.

Two more left. One enablement metric. That's completely overrated.

Number of certifications, number of trainings. Doesn't matter. Don't give.

All right, last and final question. If enablement were a Netflix show or a movie, what would it be?

Let me think. Am I taking too much time for a rapid fire?

It's okay. We'll. We'll cut the time we took for the last one. I think you did it really well. It's the last one. You're taking time.

Okay. I'm trying to think. Wow. If it was a Netflix show, I got round. I'm not able to think. Give me a moment. Okay.

I can give you the answer I.

Want to give you. You want to give me an answer? You want to give me an answer? Okay, what's the answer?

Enable or die trying.

To. That's a good one. Is that a show?

No, the show is. The show is not. This show is get rich or, you know, die trying. So I'm just saying enable or die trying.

Wait, no, I want to think of a funny story. I found one. Wait. Okay. Ask me.

Okay. For a Netflix show or a movie, what would it be called?

It would be called Stranger Pinks because of all those unlimited slack messages and last minute requests that we get.

That's amazing. I love that. All right, so, Rajee, this was definitely packed with insights from AI powered coaching. We discussed that a lot towards the broken enablement. I know a lot of sales leaders and leaders are going to rethink their program after this. To everyone's listening. If you're in sales enablement rev ops, you want to stay out of the car. This episode is your playbook. Thanks again, Ruchi, for being here. Let's do this again.

My pleasure, Rahul. Thank you for having me.