Sales Enablement—Teach Reps Through Feedback with Thomas Cheriyan

Foreign.

Welcome to the live Better Sell Better podcast with your host, Kevin Dorsey of Inside Sales Excellence, the number one Patreon group and YouTube channel for tech sellers and tech sales leaders, where we dive in deep for tactical advice on how to book more meetings, close more deals faster, and lead sales teams to success. But we don't stop there. We also focus on the person in salesperson. We talk about mindset goals, time management, and so much more. So thank you for listening and if you're interested, head on over to patreon.com InsideSalesExCexcellence now with that, grab a notepad, get ready, and let's dive into the good stuff. But first, a quick shout out to today's sponsor, Vidyard. If you aren't using video in your sales process, I promise you, you are leaving money on the table. I personally have been using Vidyard with my teams for years now and we use it everywhere. Top of funnel to book more meetings via email and LinkedIn, middle of funnel to improve show rates, to demos, post demos to do proposals and follow up.

And close deals faster, react or whatever to do their job. And salespeople just need to learn cold calling to do their job well. Sales enablement, the way I've defined it with my team and here within on backup, it's a philosophy. So, so what are not only the skills you need, but what is the process, the technology, the tools, essentially the entire ecosystem or environment so that you're truly being set up for success. And so from that perspective, my team is working on not just the skills training, but we're deciding which technology and tools we need to buy. We're helping to determine the architecture of those tools. Right? So we use Salesforce as our CRM. And as you know, there's a million ways to implement Salesforce in a good way or in a very painful way for both the rep and the manager.

Right?

And that also in turn determines the rep behavior in terms of what you want them to do or not to do out in the market. We have rebuilt our sales stages, we have rebuilt our sales methodology, so we threw our old one out and we're obviously with Winning by Design as our new winning sales methodology partner. And it's literally just that whole ecosystem or all of those different dimensions of enablement from boot camp and onboarding all the way through the foundational and advanced skills and trainings that we need to deliver to our new and tenured reps so that everyone's being set up for success. It also incorporates things like culture, enablement, Product enablement, HR enablement, all of these other things we take for granted, but we gotta make sure our reps are mindful of all of these things so that they're doing their job well.

And I think it's funny. This is why I'm not allowed back at the Sales Enablement Society. At least I haven't checked in in a while because of, like, four or five years ago. I was like, we need to change it from sales enablement to sales success. Because if we're not actually able to tie back what we're doing to sales success, then what are we really enabling? Right. So if we go another layer deeper here, like, what are some of the things that you have seen to work, or maybe even more powerful things that you've seen not work in terms of actually enabling the team? Because one thing to call it sales enablement, but we actually need it executed across the team. We actually need to buy in the execution. So, like, what are things that you've seen to be successful, to actually get what you have and what you're doing implemented by the team?

So one of the first things I did when I started at OWN Backup over two years ago was I just wanted to listen. I didn't want to come in with my own assumptions or just take my own personal bias and experience or authenticity, and it would feel foreign to everyone. And I didn't want to do that. So the first thing I wanted to do was understand the current state. But I also understand. Wanted to understand, like, what are our average reps doing along with our top reps? And that uncovered a few things. I understood that our top reps were actually delivering a different pitch, a better pitch than what sales and marketing was teaching our reps. And I wanted to institutionalize that. They had their own process which was not aligned with what we thought our process was. So I wanted to institutionalize that. It's amazing what you can learn from our. From your top reps. Yes. From a new hire standpoint, we had this thing called boot Camp. And I told my boss at the time, I don't know if I should be saying this out loud or not, but I will. But it's like, dude, you hired me to really own Bootcamp and everything. Enablement. And I'm telling you, as a guy with an engineering degree with an MBA, with over 10 years of enterprise sales experience working at Gartner and Yelp and all these other cool companies, I have no idea what OWN Backup is. I don't know our pitch, our products, our services, and if you're asking me just as a rep, to sell this solution or product, like, the week after bootcamp. I'm screwed. I am beyond screwed. Like, I am scared. I actually want to leave. He's like, no, Tom, don't leave. This is your baby, and this is where we need your help and we need to rebuild this whole thing. And so I had to rebuild and re architect that, But I wanted to do that in the lens of, like, okay, what are our top reps doing? And then I also. Because the other thing I do outside of on backup is I'm also a professor. We're going to get into this.

I'm excited.

So. So I have. Consciously or unconsciously, I understand how, like, just people learn. And I know from a rep perspective, I can teach you the pitch, but I need. You need to show me also that you know the pitch. So one thing I know that we're doing, and I haven't seen a lot of other companies do this, but we make boot camp immersive and engaging. One of the things we do is that we ask. We actually ask all of our employees, but our sales reps in particular give me the pitch. Right? And not from a sales perspective, but like, let's pretend we're at dinner and I'm interested in learning more about OWN backup. Maybe you want to refer me into own backup. Well, how would you pitch it to me from that context? Right. So it's not a high pressure thing, but you still have to deliver the pitch, right? What is the problem and what is the value or solution that own backup solves for that problem, and that gives everyone the confidence along with the skills and the knowledge that they need to be set up for success. So I've been. I've tackled it from day one, multidimensionally. It wasn't like, hey, here's like, the silver bullet to solve for it. It's like, no, I gotta see what our top reps are doing. Clearly, they, you know, they're doing a different pitch. I need to rebuild that. We don't have Personas. We need to build that out. We need to have a new methodology. We need to build that out. We need to rebuild bootcamp. We need to have a way to deliver training asynchronously. So I joined, like, a month before the pandemic, and when the pandemic hit, okay, well, even with the playbook I'm inheriting, I gotta throw that out and then some and build everything from scratch. And, you know, even though things are better, you know, we built something that Works virtually and in person and remote. And, yeah, it's been a win, win, win across the board for everyone in sales at OWN backup.

And I love how you started that description, because I cannot tell you how many enablement teams I've talked to that literally never talk to the sales team that they're actually at odds of. Like, oh, yeah, our top performers do it totally different. I'm like, cool. So, like, what are you learning? Oh, no, we're teaching this.

Are you listening to yourself?

Right now?

You're fighting the top performers versus taking what they're doing.

We call the internally scaling greatness. So every quarter, I have my managers focus on the positive outliers. Who has the highest close rate.

Why?

Who has the highest deal size, who has the fastest deal cycle, who books. And, like, it was the shift because we always focus on what's wrong. Study greatness. Right.

So now let's go another layer deeper.

You're starting to touch on this a little bit. Okay. So you find out what the best you're doing. How do you kind of roll that out or create a program around it, like. Or a process. You said process a couple times. All right, you study greatness. You find out this is what the best are doing. How do you create a program for that that then kind of builds that into the rest?

Sure. So I'll give you. I love. Because I teach and I teach through, like, the Harvard case study method. Let me give you some case studies. Let's go.

Let's go.

Because I think it'll be relevant to you, but whoever else is listening, it's like, just don't give me the theory or the bullshit. Like, tell me what you're actually doing, so I'll tell you. So first off, like, let's take bootcamp as an example. I've consciously made it a point not to have sales leadership or even myself deliver on the skills or trainings that a rep needs to own. So what I mean by that is, when it comes to our top reps, let's say doing discovery, and doing discovery really well. Well, why would I have a sales leader do that? Or me or someone on the enablement team do that versus actually having those top reps do it themselves.

Yes.

Yeah. So, uh, maybe it sounds, like, controversial in another company, but for me, I don't need the spotlight. I don't think sales leaders need the spotlight. I actually had an AE who was delivering the disco training really well. He got promoted to management, and I had to, like, give him a hug. Like, dude, I love you. But I need. I need somebody on the ground that is practicing this as a practitioner every day. Because the way we do discovery this month is going to be different of how we do discovery next month or next quarter. Right. The landscape changes, the market changes, seasonality changes. Right. So we need to have reps, teaching reps. And that's awesome because that means it's authentic. It means it's credible. Right. The knowledge transfer actually sticks. The Q and A and engagement, it's different because people just want to get real and get. Get. Get deep into what their peers are doing. And so that has elevated the boot camp experience.

Hold on, I want to jump on that one real quick.

Yeah, yeah. It's a good case study. Yeah, go ahead.

So love it. I literally had a call, literally this morning. I was walking a company I work with through what we called tribal training. Right. There was a training with a tribal training. And funny enough, actually learned this, I think was from. So one of the books on learning I have on that top shelf there of like, that's actually how we've learned for our entire, like, call it species until recently, where we had, like one person trying to teach. We learned from the tribe. And so pulling in the tribe and teaching is a huge tactic. So I love to hear you. I knew we were going to vibe on all this. But a question I get asked, and so I'm going to ask it to you is how do you incentivize that top performer to do that? Or how do you get that top performer to. To engage in a boot camp when that's not their job or that's not whatever else? I get asked this all the time, like, how do you do it? How do you approach that? This is a top performer they could teach. How do you get them involved?

So there is no. I just wanted to call it out. There is no incentive. Right. I'm not giving anyone a gift card or even a pat on the back. I mean, I am very in much in gratitude of the time that they're willing to share. And I make sure everybody in bootcamp understands that this person could have been prospecting or closing deals or doing a million other things that would help them with their pipeline and revenue, but they chose to share this time with all of you. So, you know, from that sense, that's. That is what I do share. But I. The. It all starts with culture. And the culture, at least of own backup, is that it's. It's. It's tribal and it's community driven. And I think what I've done is I've made it. I've made Bootcamp as one of those institutions where, first of all, if I'm reaching out to you, like, that's. That's a good thing, right? That's not a bad thing. And look, nobody wants, you know, people want to move up or around, and this is an opportunity to. This is one of the few opportunities to build up your personal or professional brand name within the company and to leverage that to move up or sideways or whatever. So, you know, because Bootcamp is so visible, because Bootcamp has such an impact, my theory, and I haven't done a survey or anything, so I'm just talking out of my butt right now, but my theory is people really see the opportunity to speak and present at boot camp as, like, an opportunity to build their brand. But I also feel like they get the sense of feeling that I do that it's. It's just beyond rewarding, right, to help others out and to be, you know, quote, unquote, like a. Like an influencer or a teacher or a professor in that context. And, you know, I think, you know, there's very few people that may have that Persona or personality to, like, just give back, but it does take a community to raise a child. It does take a community to raise up a new hire. I think, you know, we were doing boot camps like, six, seven hours a day for five days a week, and I have about 30 to 35 people actually helping me to deliver content throughout Bootcamp. So it's not just me. It's not just like the five folks I have on my team right now. It's literally top down. So from our CEO, our CRO, our cfo, our cto, I pretty much have the entire C suite to individual reps and SDRs and AES delivering and contributing content throughout boot camp. So it's. I can't. Yeah, it's the entire tribe.

I love it. I love it. And that's what I was. Because, like, people ask that question, like, how do you incentivize them? I was like, I don't. I just ask them if they'd be willing to do it. And 90% of the time they say, yeah, it's like, yeah, that'd be cool.

Yeah. And one of our core values is we care about everything we do. And so I think it actually says a lot if the CEO, right, for a multimillion dollar company, is willing to take time out of his day, out of his week to show the vision, the strategy, talk about our values, and make it very Clear that it's coming from the top down, but it also has to come from the bottom up. Right? And, you know, that's actually one of the ways he ends his session. Sam Gutman. He doesn't own culture, but it's. It's everyone within own backup to the individual contributor. So we all contribute to it. And I'm also conscious that the folks that I'm reaching out to, like, are they cultural ambassadors? Do they have. Do they. Do they exemplify that in what they do and how they do it in their respective roles? Because. And even if they're doing a lesson on discovery, like, it's not just about discovery. It's about those core values as well. Right? It's about how do we do discovery with, you know, if I'm trying to sell to you, Kevin, but doing that with the lens of care and value and all those other things. And that's actually what our customers rave about. This is the only company, by the way, that I've worked at or I've seen where, you know, if you look at G2 Crowd or the app exchange on Salesforce, our customers are writing about our reps. Wow. Our reps. And about our customer support people, folks. Customer supporting customer success. Yes, there are reviews about the product, but the majority of the reviews are about our people. And that's also one of the things we're using Boot Camp. Like, it's the people that make this company. Yes, the product works. Yes, the product is awesome. But it's the people that drive it home. It's the people that are the reason why our prospects are buying from us. It's definitely not our price.

You're getting some job applicants after this. I can promise you. Like, this is amazing. Okay, let's keep going now. So I jumped in. I ruined one case study. What's the next case study of, like, okay, we got new hires. Because, again, this is where people go. They go, well, that's new hires. It's easy to impress new hires with the veterans, right? How do you enable or roll things out to maybe the. The greater crowd, Right? Like, people that have already been there. We need to change behavior.

So it depends on the context. So, for example, we're at a stage of growth where we're rolling out essentially a new product once a quarter or once every two quarters. So, for example, we have a new product rolling out within the next month or two. ServiceNow. Backup and recover for ServiceNow. So that's something we have to do with the entire company. And so one of the things that we're mindful of. It's not just about the product and how it works, but the ecosystem. Right? What is ServiceNow? Because even though IT decision makers know what ServiceNow is, nobody at home backup knows, right? Because that's just not the world we live in. So what is that ecosystem? How does it work? Why. Why do customers love them? Because we need to resonate with them. Who are the Personas? Why are those Personas important? What do they care about? Right. Emotionally and rationally? And again, show me. You know me, right? And so with the entire company, it's leveraging a platform like Brain Shark, where we can do those asynchronous stand and delivers. So they record themselves doing the role play, the pitch, the objection, handling. They get feedback from their managers. And one of the things I've been conscious about, and this is just how people grow. You grow through feedback. It's not necessarily about me teaching you something. It's about me giving you the feedback based on how well you've actually understood it and mastered it. And so what I've done is I've been measuring and architecting and measuring these feedback loops. And so brainchark as a platform is amazing because I can report back to my CRO, hey, I've. I documented over 4,000 times in 2022 or 2021 where we've given this type of explicit feedback for manager to rep. The other story behind that is I had this one rep. She complained to me. She's like, tom, I had to record myself over 17 times before I felt comfortable giving the pitch and submitting it to my manager. And she was frustrated. She was like, beyond frustrated. Maybe she wasn't, but she, yeah, she conveyed it in that way. Like in a sarcastic, but maybe not so sarcastic way. And I told her, like, look, that you. First of all, I applaud you for doing it 17 times. You think any prospect would have taken, would have just did like a Zach Morris, you know, saved by the bell pause, right? Like during your pitch and be like, hey, let me give you feedback so you could do it better next time. Like, it's never going to happen with the prospect. But the fact that you're able to do it 17 times and you reflected on it over 17 times and then you felt comfortable doing it for your manager. Like, do you feel like you're better for that now? And she's like, yeah, mission accomplished, right? So that, that's how we drive change from that aspect. And, and that's. And that's what the tenured rep that wasn't with the new hire. Right, Right. So even tenured reps, no matter how long that they've been with the company, they could struggle on something, and that's okay. Right. But are we giving them the means to get to do that reflection and to get that feedback? And I think that's the hard part. Like me telling you something is one thing, but if I can create a situation where you're getting that feedback and you're getting that ability to self reflect, that's even better.

And that's what I break down with a lot of managers, even in the courses I'm teaching is like, if there's not feedback and doing, it's not coaching, it's teaching. Right. You're teaching if you're just transferring the information you're coaching when you're giving feedback and they get to do it again with that feedback. That's also where I think a lot of managers go wrong, is they listen to it once they give the feedback, but they don't realize the rep still hasn't done it with that feedback. All they did is they got the feedback. They still need to do it with the feedback.

Right.

So then this is kind of segueing into the next point because when I was looking up your background, I also see that you're a professor, right? Which like I said, wait, how many roles? Okay, we don't have enough time for all this. I was like, okay, but also a teacher, Right. And so actually behind me, half that bookshelf up top is all on the science of learning. Because about three or four years ago now, I was like, okay, like, as a leader, like, maybe, maybe people aren't catching what we're teaching because we're not teaching it. Right. We're not actually presenting in a way that empowers learning. So, like, how do you take what, you know, as a teacher, as a professor, and weave in that? So the retention is there. So I hear this a lot from enablement too. Right. It's like, oh, we taught them it, we taught them it, but it didn't stick. Okay, what are some of the things that you inject into these processes that have, like, the science of learning behind them?

The science of learning. This is probably where I have to say, I don't know. But I will say this because I'm modeling the way I teach through the style of the Harvard case study method. There is a lot of science behind that. It actually took me a while to figure that out. I'm wrapping up my seventh year now as being part of the faculty at the City College of New York. But I reflected back on, like, who are the best professors I had, especially in graduate school. And it was those classes where we were using Harvard case studies to learn from real life examples, not from a textbook, and then have that furious, constructive debate with one another and everyone's just, like, fighting it out and.