Sales Enablement—Teach Reps Through Feedback with Thomas Cheriyan

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This is.

This is your host, Kevin Dorsey, AKA kd. And today I get to talk to what I almost consider my brother from another mother here, because I was introduced to Thomas Cherrion at OWN Backup actually through a sales call. And I got to watch this man work this sales call in a way that instantly gathered my respect. Because what a lot of salespeople don't understand is that you don't buy software, so you don't actually understand what it's like to be a professional buyer. As much time and energy that goes into the sales side on how to sell things, there's just as much energy on the flip side on how to buy things. And so we're going to dive in today of not only what it's like to be a professional buyer and what we think about, what we look for, how to work with us, but then also how we can take this and enable our teams. Because Thomas is also the Senior Director of Learning and Development at OWN Backup, and he's A former salesperson, so he gets it. He knows how to sell, how to enable and how to buy. We got the triple threat today, my friends. Thomas, welcome to the show.

Kevin.

Kevin.

Kevin. So awesome to be here with you.

Let's do this, man. I've been looking forward to this one all week, so I'm pumped. So, okay, we're going to start like the style of the show. We get into it, we get into the trenches very quickly. I want to start actually with enablement and then we're going to work to buying, right? So this term, sales enablement, been a hot term now for a few years. More and more companies are building out orgs and everything, but I don't think the industry has actually done a great job of defining what it is. So when you say sales enablement, when you say learning and development, what does that mean to you?

So two things. So first of all, sales enablement and L and D. It actually has like two different philosophies, right? So when I think of L and D and I'm biased, but I think of L and D is just like skills training, right? Hey, what are the skills that person XYZ needs in order to do their job or thing well, right? And so you can think of it as like developers might need to learn, 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 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, you know, 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, because this is why I'm not allowed back at the Sales Enablement Society, at least haven't checked 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. Cause 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 experiences from my previous employers and just roll them out. I mean, I would have no credibility 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, like, 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. And 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, multi dimensionally. 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 boot camp. 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 got to 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. 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. 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, you know, 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, don't. 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 have 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 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. 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 bootcamp 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 is a train with a tribal training. And funny enough, I actually learned this, I think was from 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, called 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 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 you 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 much in gratitude of the time that they're willing to share, and I make sure everybody in boot camp 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 from that sense, that is what I do share. But it all starts with culture. And the culture, at least of own backup, is that 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 boot camp as one of those institutions where, first of all, if I'm reaching out to you, that's a good thing, that's not a bad thing. And 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 just beyond rewarding, right, to help others out and to be, quote, unquote, like an influencer or a teacher or a professor in that context. And I think there's very few people that may have that Persona or personality that they'll 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 Bootcamp. 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, 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, like, 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, they're also. 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, 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 and 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 own backup knows, right? Because that's just not the world we live in. So what is that ecosystem? How does it work? 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 brainchark 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, 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 what 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 was like, 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. Because 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 who are the best professors I had, especially in graduate school. 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 fighting it out and people have to not only just present their argument, but defend their argument. It's kind of hard to do that in sales training. But I am doing everything that I can to teach through real life example, to foster positive and constructive debate, to give everyone the opportunity not to just to pitch the act of pitching or role playing, but to do it with senior leaders within own backup. So first of all, it creates that sense of pressure in the room. Like, holy crap, I got to present, I got to do the stand and deliver with this RVP or this VP of sales. And it's, it's, it's interesting. I never expected this to happen, but I guess because we're hiring so many people and you know, everybody gets connected to everyone else, it's like, hey, you better prepare, you better get ready. And I'm seeing people come in with their scripts and that's one thing I haven't done in sales enablement. There's not a single scripted pitch or role play that anyone can find. Maybe other people have done it. I haven't, I haven't institutionalized that. I've given people the frameworks and the content that they need to deliver a pitch, but it'd be impossible to script it out for every Persona and industry that exists. So I see them coming in with their notes. That's awesome. The other way we're doing it, I forgot my train of thought.

It's all good. It's because you're too, you got too much stuff up there right now. So what?

It's a lot. But the stand in delivers, I think, exemplifies that. The way we deliver content exemplifies that. The culture where people can interrupt the presenters and do Q and A and ask engaging, thought provoking questions. Oh, and the other thing that we do that really ties everything home is we bring in the voice of the customer.

Yes.

So talking about the customer is one thing, but for every freaking boot camp that we do, we have one of our amazing 4000 plus customers come in virtually or in person, and they literally present on their journey? What was their pain point? What was their situation? Why did they end up buying what they buy from OWN backup versus the other options that they did have and just elevating that journey, but also giving our reps and everyone else that's in the audience the opportunity to do Q and A and really get to understand them just more as a human. Not just as a buyer or a Persona, but as a human Persona. Everybody does Persona training, and it seems very foreign. I didn't really understand. I know the value of Personas, but the value of talking to a real Life customer is 100 times more important. And so to bring in that voice, and we bring in a different voice every boot camp, so there's always a new perspective, and it's open to the entire company, whoever wants to join. It's not just for new hires. So everyone just. Just the excitement, the elevation, the. The endorphins, like, it just goes up, and that's just what elevates the experience.

And he just tapped on something a little bit there. All of that improves retention and learning, right? Positive chemicals being released in the brain, the dopamine, the serotonin, and the oxytocin, creating a positive learning environment increases retention, it increases attention. And, like, the culture. I'm just getting fired up on this, dude, because I never get to talk to people, like, do this. And this is amazing because it's so much. And I hope people listening are picking up on how much culture can drive this. When people are talking to each other like, yo, you better prep. Like, Tom's gonna get you if you're not prepared, right? Oh, you got the vp. Oh, like that. When you can create a culture around that. Like, I guess I got to ask this, like, was that already in place when you joined, or how did you help create or craft that culture? Like, I'm a big believer. Ben Horowitz, in his book, the most recent one, what you do is who you are, he says, if you're not intentional with your culture, it'll happen on accident, and you don't want an accidental culture. So, like, how. How have you crafted that? How have you helped build that out? Because that's just so strong.

Well, look, first of all, if I made it seem that way, I should take zero credit for it. I didn't build our culture. Our CEO and our founders didn't, and they built the core principles of our culture. And one of those pillars that resonates really well with me is, like, we care about everything we do, and so it's Just with that culture or that value, where I'm thinking, okay, if I really care about boot camp, and I do, and I've been a sales rep before, I've gone through what other companies call, you know, quote unquote, boot camp or onboarding. I don't want to name my previous employer, but it was literally, I think it's like this maybe today with most employers where you just get up, throw in a laptop and then that's it, right? And this is a pretty big, well known company and it's like, dude, you're giving me a laptop and I have to figure this out on my own. Like, what? Yeah, no, I didn't want to do that. I know firsthand, like, it sucks starting at any new company, right? There's anxiety, there's angst. Like, you literally, you don't know what you don't know and you have all of these other feelings. And the worst feeling of all is buyer's remorse, right? And we hear about that just in any sale, right? But we don't really talk about it from a new hire dimension, right? But there is buyer's remorse there. Like, did I really join the right company? Should I have accepted that job offer or should I continue that interview process with that other company? Or let me just go back on LinkedIn and just, you know, maybe, maybe I'll update my LinkedIn profile a month or two later and I'll just keep putting some fillers out there and see what happens. No, like, how do, how do we squash all those things immediately get people committed to the culture, the mission, the values, and just be ramped up for success. So what was the question again?

I mean, it was really just like crafting that culture or like building. Obviously it starts at the top and I love the humility there and I understand it, but at the same time, the culture can be defined at the top, but it's lived in the bottom, like you mentioned. And that's why I'm asking you how you've weaved that in. Because every company has values. Everyone talks about their culture. But like, your squad and your team is living it right now. And I just, I just love it.

Yeah. Yeah. So nobody, nobody told me I was a cultural ambassador. I just owned it because I knew I'm one of the first touch points of a new hire's journey at own backup. So first of all, I had to believe in it, but I didn't have to because I already did. I was bought in the culture and the values just resonate with my own personal Values. And I made sure that every person that I brought onto my team also exemplified that from a new hire experience. I just, I wanted to do really the, I hate to say the opposite, but really the opposite of every other company I was with or every other company that I knew of existed and what their experience was. And like, I wanted to create something that was just unique. Like something like, it's not rocket science, but it's like, what the hell? Why didn't I think of this before? Like, I don't know why it's controversial or crazy to have a customer speak to your new hires. Like, you know, some companies, they might think like, oh no, that's sacrilegious. They can only be used for case studies and infographics and maybe some kind of VIP dinner or something. It's like, no, absolutely not. And we have more than enough customers to, to do all of those things and then some. But it's like, no, we, we need, we need to bring the customer to life, right? Case studies don't do that well. Like, that's just the reality. Anything that's like scripted or curated, it's not authentic. Right? But let's, let's get the authenticity and the voice of the customer with our new hires and let them see it firsthand. Because it can't just be me and the leadership selling them on why and how to sell them back up. Let's hear it from the customers themselves and then they can take those stories, obviously with the customer's permission, and share it with whoever they're talking to. Like, hey, I recently had the chance to speak with this salesforce admin of this bank and this is why he became a customer bound backup. And by the way, I'm not telling you this from a case study he literally presented to me at our new hire boot camp. This is what he or she said. Does this story resonate well with what you're trying to go through as well? And it's like, yeah, I love it.

I love it like that. I call people, I tell people. It's like, if you have no enablement budget, no enablement, like people, nothing there. You want to duct tape an onboarding program, Let your new hires interview 20 customers.

Even if you had a million dollar budget, why wouldn't you do this? Right?

I was like, you need to do this. You have to record it. It goes into the playbook, all these stories, like, to your point, like, why is that controversial? I got in trouble at my last role. Got in trouble because in the first month I started calling Customers and asking them questions, and they're like, you should have come to us first. We would have given you a list. I was like, I didn't want your list. I wanted to talk to customers of all spectrums. Good, bad, happy, sad. Like, we need to be able to talk to them in sales. We have to.

Yeah. And I think, for the record, I didn't ask for permission. I just did it. Like, I'm going to get a million reasons not to do it, but let me just do it anyway. And then once I did it, it's like, okay, Tom, you have to keep this going. So I'm a big believer of just, like, do it. If you screw up, you know, you ask for forgiveness later. But, you know, knock on wood. I think 90, 95% of what I've done has been received well.

I love it. I love it. All right, so, like, I don't normally do the background questions on the show, but I'm just deathly curious. How did we lose you to enablement? So you were in sales, you were in management. You're a leading enterprise.

Yeah.

How do we lose you? How do we lose you to enablement? What triggered that transition? Because obviously, dude, you are good at what you do and really good at it. Was that a choice? Was it an opportunity? What caused that shift?

So, yeah, it's a good question because I think, first of all, unconsciously, whether I knew it or not, this was always my calling. And really what happened was, you know, I spoke with some mentors talking about, like, hey, what's the next thing I should be exploring or doing? Because I've been a sales rep, I've been a sales manager. When I was at Yelp, I was managing over 33 million in revenue for the company. Like, I know what I'm doing when it comes to just doing enterprise sales really, really well. But what. What I really enjoyed was, like, the training and the mentorship. But what I didn't know was that there was this thing called sales enablement. And then once my mentors told me, like, hey, there is this thing called sales enablement. And this is what the job does, minus the quota, minus the commission. I'm like, really? I really got. I really love the commission. And by the way, every day I regret it in a good way. It's like, I see what the reps are doing at OWN backup and it's like, oh, I just need a.

Just a piece. Just a piece.

Like, hey, hey, orey, who's our CR? Just, just. I just need 10 accounts. Yeah, yeah, just give me 10 accounts, I'll do something on the side. But, yeah, no, it's. It's where my passion is. And I think part of that passion led is a result of, like, I. Especially as a sales leader, I know what it feels like to not have good enablement. Like, and it's. It's. It's. First of all, it's painful and it's time consuming. Right? Like, I have to do everything myself, and it's not scalable or repeatable. And I'm like. Because it's not. Even though it's important, you just, you know, you're not doing it as well as you could be because it, you know, like, you can't, as a sales manager with your own team, run a bootcamp experience. Not when you're trying to onboard and help all the other reps with what they need to do, closing business and everything else, or even as an individual rep, like, you just can't do it. So that's why I reflected back, really, on those experiences and thought about, okay, I have an opportunity here. And I have the autonomy, too, which is important. The autonomy, the respect, the authority to build something epic here that I can be proud of, the company can be proud of, that the community can be proud of, the sales enablement community. What.

What.

What can I do that can really take things to the next level? And so it's just reflecting back on all of those experiences that could have just been a thousand times better. And like we were talking about before, it doesn't cost anything to have a live customer present. And it's just like asking those dumb questions out loud. And it's like, okay, well, I'm going to do that. I'm going to do these other things. And then boom, boom, boom. Before you know it, it's like, this is. This is awesome.

You've mentioned a few things that cost no money. Okay. Customer costs no money. Tribal training costs no money.

Doesn't cost. Yeah.

And it's actually more impactful that recording role plays costs no money. Yes, you can use a platform, but you don't have to. You can record it on zoom on your phone. Like, there's so many things here that are like.

It's just.

God, this fires me up, dude. This is so good. Because, like, this is not so for everyone listening. And you already know this listening. This is not normal what Thomas is talking about right now. Like, what he is doing is beyond unique across the SaaS industry. Because this is not how most companies run bootcamp. It is not how most companies run L and D and enablement, like it's just crazy to me. And I looked up. We're already at 45 minutes. It's like, dang it. I knew it. So we're gonna have to do a part two here.

But why can't we just keep going? Let's just keep going. Why can't we keep going?

Okay, we're just going to keep going. Whatever Joe Rogan style.

It's the Internet. Just pause. Just pause. Later.

Yeah, we're still going to rock. So let's make the transition out of buying because I do really want to touch on this.

Can I just make one point?

Yes.

I just, I just want your people to know, your listeners to know. I don't have. I'm not using any crazy tech and tools. I get this question a lot. Like, what's your tech stack? I'm not using any crazy, I'm not using any call intelligence software. I don't know what other tools are like no fancy AI or analytics. I'm using Google sites to post my content, but I built it. That's literally on par with like the top, I guess, CMS platforms, lms.

Cms.

Like yeah, we're using Brainchark as our lms. I can't, I can't put a shoestring thing together like that. But with all of our other content and with Brain Shark and everything else, it's like just Google Slides, Google sheets, Google sites, hosting all of our content together. Spec has been a good provider, but just, yeah, just. You don't need a million dollar budget. I'm definitely not spending a million dollar plus on tech and tools.

And that's where. And you know that you absolutely know this in enablement.

Right?

Like so many times people think that tool will solve the problem.

No, it's the opposite. If you create more problems.

Right. It either amplifies. If you have a problem, the tool will amplify it. If you're doing things well, it'll amplify it. But the tool doesn't solve the problem. You got to solve that problem first. Right? Okay. All right, now we're going to transition. Thank you for that call out. Because that is always the follow up. Like, oh, you're at own backup though. Oh, you've got all the resources and it's like, no, like creativity is the.

Reason I feel like I'm struggling like every other any aboliant leader. Like I could definitely use more money, more budget, more people. But that's why it's so much more important to scale with the resources. You do have and to get executive buy in and to build those champions or alliances with other key leaders and reps and managers across the org, because that's how you build an impactful program. It's. That's more important than the size of any budget.

100%. I know plenty of teams that have way bigger teams, way more budget, that are not operating the way that your squad is operating. And that is just unreal. Just unreal. Okay, now let's talk about buying. Let's talk about buying. Okay, I want to take a second, and I want you to put your buyer's hat on. We've had our enablement hat. We've talked L and D. We've got that. We're going to shift to the buyer's hat here real quick. All right, so. So what is it that salespeople should know about buyers that would help them close more deals? Let's start there. This is not how to pitch. This is not all that. It's like, what should they know about buyers when someone's buying a product that, if they knew, would help them close more deals?

This is going to sound really dumb, but I'm just going to, yeah, I'll just say it out loud and then I'll play it back later and be like, yeah, that was dumb, but I'll say it out loud. But I think, look, it's kind of hard because, like, when you're, first of all, as a rep in any company, like, you're taught, hey, this is our sales process. These are the sales stages. You have to do step one, step two, step three, and you feel like you're stuck in this box and you have to do these things in a consecutive way. And that's how the magic happens. That's how you get the deal done. And I think the frustrating part, and I see it, you know, with hundreds of vendors that are trying to solicit to me and my team, they're not selling to me the way that I want to buy. Right? And I think that's the disconnect. Right. I respect your process and how you need to do what you need to do. But as a buyer, I also have a process and how I buy. I'm not the only buyer.

Right.

And actually, the reality is I'm not a buyer. I just said it. I don't have a budget or I do, but I'm not. I'm not the one signing the order form or the contracts. Right? It's, you know, you have to talk to legal. You have to talk to my cfo, my CRO, like all of these other stakeholders. And again, at the end of the day, even if I'm your user or your champion of this product, it's like, are we creating a connection? So one of the things, by the way, I teach with my reps, is a term I coined up two years ago by accident. And this is what I was shadowing with our top reps, which, as a result, made it really easy for their prospects to buy. And it's called the oh, shit moment.

Yes.

All right. And so the oh, shit moment is when you're creating that feeling with your prospect where it's like, holy shit. Or, holy crap, we should have bought you guys yesterday. Right? And so I think the process the companies do or the reps that do that really well create that moment, and that just basically gives you the layout for the rest of your sales process. There is really no other tips or tricks. There is no fancy collateral. I don't want to read a white paper. I don't want to read a case study. I don't know why you're sending it to me. I don't want to read it. I can't imagine anyone who does. I like seeing who the other customers are. I don't like to see factoids like, hey, this company saved 56% by switching to us. I'm like, red flag. I mean, as an engineer with an mba, I will happily tear that apart and call BS on it. So, like, I'm already, like, suspicious at that standpoint. But, like. But I do love stories.

Oh, 100%. You have to have stories. Not case studies stories. Like, I've had sales reps send me things of like, so based off our breakdown, you are going to see a 7x ROI on our product. Right? I go, can you do math? Do you understand what 7x would mean to my pipeline right now? I've got 125 people prospecting. You understand 7x would mean you would be generating me $50 million in pipeline A month. Where did you get that number? Like. Like, where is this ROI coming from? So go for it. Jump in.

I was going to say, that's why I consciously tell our reps, and some of them look at me crazy. But. But I. And I kind of do this near the end of boot camp. I make it clear, like, there's a reason why I'm not. Not once through your new hire journey, we talked about roi. Let's focus on impact. Let's focus on what we're able to deliver. Right? On the problem that we're solving for. But once you go down that ROI rabbit hole, it's lost. I think about my car insurance with geico. Like, knock on wood. I haven't been in a car accident in over 10 years. 12 years. I think it was like when I was 24 or 25 and was my friend driving my car. But outside of that, I haven't been in a car accident. Knock on wood. But do I have a negative ROI with Geico? Should I cancel my car insurance because I haven't been in a car accident.

Right.

Have I just been donating my money away? No, absolutely not.

Right. So roi, it's like, that's where it's hilarious. Sales reps do this. Buyers don't. With all the tools I have ever bought, I don't think I've ever sat down and actually said those words. What's my ROI going to be on this ever? It's been, will it work or will it not?

Right.

And what does good look like? What do I hope I get out of this compared to what I have right now? And is it worth the cost? Not what the ROI is going to be?

Yeah. So as a buyer, I see anything like that, it just creates cringe within me and I have to click on the spam button and just move on.

Yeah, yeah. So that's one my reps, companies we work with, I'm like, don't you ever tell someone you can X anything if you haven't spoken to them?

Yeah.

Even imply that you can X anything. You don't know what my ex is. You can't 2x it if you don't know what it is. Like, how dare you. Right. So we've got that side of it and let's keep going down this process of like, what does stand out to you as a buyer? Like how so like if you think about the buying process you mentioned, how does a sales rep actually help you buy?

I think if I should talk about how our reps do it, then it all makes sense from, from that other perspective. So one of the things we teach our reps to do is create something called a mutual action plan or a project plan. And that's where I see a lot of vendors who are trying to solicit to us. Like that's where they fail. Like they, they schedule like that 30 minute or hour long call with me and for whatever reason they feel compelled to do the demo of their app. And you know, I'll tag my team and we'll, we'll just enjoy it. We'll ask them A bunch of questions, but like, you know, outside of not creating the oh shit moment and not giving us really a compelling reason to do go after that, if they, if they do end up going past that stage because we, they did create that moment or we did want to continue the journey, a lot of companies don't do this, but they don't take a step back to understand, like, how, what is the process to help me buy, like just buying in any company. I don't think people realize this. It's painful. Like, if I, if I want to buy, if I want to buy a stapler, there's a process, okay? And it has nothing to do with the company. It's just like companies at a certain size have a process and if you know what is the process. And so what we teach our reps to do is between, you know, after the demo, like, take a step back with your prospect. Let's start mapping out their journey, right? Hey, if you want to have your, if you want to have this solution implemented on July 1, and that's when you want to start using, having your data backed up with own backup, great. Well, let's work backwards from there, right? Who's involved in the infosec process, who's involved in the legal process, who are involved in all of these key milestones along the journey. And let's document this out together, literally in a project plan. Like, you could use Asana or Google Docs or whatever, right? And let's map this out, because from this point on, this is a project. You know it's a project. I know it's a project, but I want to be your quarterback and help you buy. And I think if more vendors can do that, more sellers can do that, the world of buying would be a lot easier.

And that's something that's still, you know, you think about some of the simple things that you go, why don't we do this? It's like, all right, as a sales rep, you know, legal's going to get involved. You know that. So why are you waiting, first of all for that to happen? And two, how are you not ready with the most common questions that legal asks? Just give that to me. Your legal team or your SOC team is going to want to ask these things here. I'm like, thank you. Here, Ops, read this. I don't know what any of this means, but here. And no one helps us buy. It's all on our end to buy. It's a nightmare.

Yeah. And by the way, based on that journey, can we do start Doing things in parallel versus consecutively. Why can't infosec do their thing and tear us apart? And have legal do their thing and tear us apart? Right. They're gonna, you know, they're gonna.

Yeah, yeah.

Why? Why do we have to wait for a month for them to redline our MSA when they could just do it now? Let's just get that process started. Even if, even if there's a two week queue. Put us in the queue now and everyone listening, y'. All.

This is also places where even if you're an enterprise, you can shorten the cycle. Like, we actually hurt ourselves oftentimes. Cause we treat it as linear. We don't get legal involved until after we've gotten this involved. And each thing stacks up versus coordinating and making these things happen at the same time. That's where you can speed things up in this process versus, like, oh, now I got to get in touch with legal. You were going to have to get in touch in legal from day one.

Yeah, Here, here's.

Here's a contract and a red pencil. Here, go. I know you're going to redline this. Start now so we can deal with it.

Yeah. And then you also understand, like, the milestones of, like, okay, there's a procurement team and they're gonna beat me up on price. Well, let's save the pricing and negotiations conversation till when we get to procurement. Can we agree on that? Awesome.

There we go. And I love the way that you phrase that because it's being honest and real with the person you're talking. Because, like, yes, I'd love to get into price right now, but we both know the moment we get into price now, before legal, before info, before ops, before everything, procurement's going to just take that and ask for a 30% anyway. So wait on that. Which is actually the last point I want to touch on. You still got one more minute for me here.

I got like five minutes for you.

Okay, perfect. We got five more minutes. Because this is the question everyone's going to hang around for is them haggling. Haggling, Negotiating. Okay. All terms are agreed to, but now we're down to price. How do you negotiate with a professional buyer like yourself?

So I think it's twofold, right? And also I think it's like part partly cultural. So I'll tell that story of, like, my dad. For those of you that can't see me because it's an obvious podcast. I'm Indian. I am of Indian descent, first generation Indian American. And you know, there's a story I love to share about my dad, who I love. And when he was helping me to buy my first car, or actually it was his car, which he was lending to me. And I grew up in Long island, we basically visited like every single car dealership in Long Island. Like, the product was the same. Like, we knew what we wanted. We wanted a Honda Civic, but he was doing his part to shop around, haggle, and get the best price. But I think, you know, when I reflect back on that, and it was. And it's been one of the reasons that threw me into the sales universe, because I knew. Sorry, can you hear the sirens? Yeah. All right, we'll own it. Because this podcast is so awesome. Yes, sirens are here. I think one of the reasons I got into sales is because if I could sell my dad, I felt like I could do anything, right? And because car dealers couldn't sell my dad and they're professionally trained on selling, right? But if I could do it, 17, 18 year old me, I could do this with anyone. And my dad was the toughest buyer. And I think part of it is like creating that empathy, right? And I think that's hard because a lot of times, like, between buyer and seller, there's like, it's a battle, right? No, it's not a battle. It should be a partnership, right? Like, I want to see you be successful, but I also want you to know you're helping me to be successful, right? And somewhere along the way, we miss that. And there's a disconnect to that. But I think the best reps are able to create that empathy between the buyer and the seller. And look from that perspective as a buyer, then I don't want to haggle as much or haggling is not really the issue here. I actually just want to buy it because you're helping me to solve a problem and that's the issue. But if I think of it as a commodity solution and you're giving me the ROI pitch, okay, you're helping me to save 50% or blah, blah, blah, whatever, okay, fine, we can play that game and that's where it can be a little adversarial. But if it's like, no, this is a partner in crime, right? This is not a vendor now, this is a partner, and this is how they're going to actually help me do more damage in what I need to do in my, in my team, in my field, in my company, then. Then you're an extension of own backup. And holy crap, like, that's a big Deal. And so from that perspective, it's mutual versus adversarial. But look, buyers get trained on how to buy and there's a million tips and tricks, right? Hey, let's give me a three year quote. Okay, well, now that I know the extent of the discount, I'm only going to commit to one year. And you play that game. I mean, there's a million things you can do or, you know, yes, you sign the order form, be like, hey, didn't we get this thing too? And no, okay, well, or whatever. But no, I, I, me personally, just with my code of ethics, like, I want to work with vendors who want to be seen as partners. And from that perspective, I want to see them happy and get what they rightfully earn so that they can provide me in return with the best value. But you know, if it's a commodity play, like I'm haggling between Staples and Office Max or Staples, then yeah, yeah, let's, let's talk about dollars and cents.

And that's where the only place I'll throw like a quick tip here y' all is always be ready to ask for something back because that's what buyers are going to do. We're going to ask for things. If we are asking for things, whether that is a discount, whether that is a change in terms, whether that is a and a line item, you have to be ready to ask for something back. And that's where I see a lot of reps miss when it gets to the negotiation of a haggle is they're just giving it all away without getting a testimonial or getting a different term or even getting it by a certain date. Like all those things have to be. We call it winning by design. The trade. We don't negotiate, we trade. You have something I want, I have something that you want. And that's the key, by the way, y', all, to not be lost. They have to want what you have. You can't negotiate with someone who doesn't want what you have. It doesn't matter. And so, my dude, I know I'm at your five minute mark. I got one question for you before we leave. Cause I asked everyone this question because the name of the podcast is Live Better, Sell Better. Cause I also have this weird idea that if we took better care of ourselves, if we had more joy, energy, fulfillment in life, that the sales would also improve. What would your parting live better advice be for everyone listening?

Take a step back and just appreciate everything that you have. Like, I think we live in a culture and society that we're always chasing the next dollar or the next item, you know, the next Apple Watch or whatever. It's like, no, those aren't really your sources of happiness, right? So just take a step back and just appreciate, like, the roof over your head, the food on the table, your family members, your kids, your partner, your friends, your family, your employment. And just if you can be content with what you have, then you don't need anything else and you're happy. That's it. Love it.

I love it. Dude, this was everything I wanted and more. Like, I'm not shocked, but it's just awesome to have the conversation. Tom, my man, thank you so much for this. You'll be back, I can guarantee you that. Like, we're not done here.

You.

But I appreciate you, dude. This was amazing.

Awesome. Thank you, Katie.

Later, man.

All right, bye. Bye, everyone.