Interview with Michael Ocean on SMTP podcast
I recently talked to Michael Ocean.
Guest (Venkat): Sales leadership involves three things: compensation, coverage, and capabilities. It’s a far better approach to help the AEs recognize why they need to do what we’re coaching them to do as opposed to me saying, “Dude, you haven’t filled this out.” We as salespeople, at least this is how I felt when I was frontline in the teams back in the day, you feel like you’re alone, right? You’re out there. Yeah, you have company and so on, but you are the one who’s representing the whole company, right? And this is another thing that I think we as leaders need to reinforce with our salespeople. It’s that it’s not just you, it’s the whole company is behind you, right? How do you get adoption beyond incentive and force? So let me illustrate this with an example.
Host (Michael): Hey, Cat, how’s it going, my friend?
Guest (Venkat): Good. How are you doing today, Michael?
Host (Michael): Can’t complain. You know, sunny but my AC doesn’t work. So I just called the management and said, “Hey, guys, do you want to fix this?” Like, honestly, it’s like 300° here. Anyways, how are you doing?
Guest (Venkat): Good. I live in San Francisco, where it’s permanently air-conditioned. Though I got to say in the greater than 20 years that I’ve lived here, in the past year, four years, five years, I’ve needed to use AC more often than I used to in the past.
Host (Michael): Before we start, tell me about the background. You got a lot of books, man. You got a lot of books.
Guest (Venkat): We have a lot to talk about there. So one of my great passions in life is apart from my wife is reading. And I read a lot on different topics. And this is just my my to be read uh slot, right? These are books that I bought that I want to read. And we have books that I have read and so on. So so uh so I read fiction, I read uh philosophy uh of various kinds, and then I also read science and not quite business but science, economics, and stuff like that, right? The books uh on at least not earlier when I had more space, they were organized as like uh novels that I want to read and then or philosophy, novels, and and tech and and other things, but now it’s all mixed up. So right now in philosophy, I’ve been reading a lot of things on stoicism and actually more recently it’s been more on Buddhism. And then when it comes to fiction, there’s a whole bunch of different kinds of fiction. And then when it comes to tech in business, I’m reading a lot on AI and other things, which which is something that I’ve been super interested in. I used to work at MEL, so that’s the Michael flag out, I don’t know if you can see it. And then I also have a laser cutter and this is my my laser printer. So what you see there is for laser cutter and printer which is my those are things that you know in interviews people ask you what is something that I about you that I can’t find in in LinkedIn. I just gave you an overview of that.
Host (Michael): I love it. I love it. Look, you said something about sci-fi at the end. You said, “Hey, this section is for sci-fi books.” I want to hear about your background first and foremost, and then we want to get into some questions around AI and what actually you know looks like pure sci-fi. So why don’t you just tell a little bit about your background, what are you working on these days and uh let us know who you are.
Guest (Venkat): So I am effectively the the CRO at Splashtop. We are a we are a remote access, remote support software company with a vision of going into endpoint management overall. But like quickly, uh led the go-to-market in like sales and marketing over the past, I don’t know, Lord knows how how long, let’s not get into it. Um uh uh in tech companies. Um prior to this, I was at a much larger company myself. Before that, I was at 8x8, which is a Zoom competitor. And I started a company, Maran IQ, which was an AI for marketing company. Uh so we got deep learning back in 2013 and then we sold it to to 8x8 who’s used it for other purposes. Prior to that, I started another company uh and I used to work in McKenzie and and you know, uh uh my previous company was like an uh like a mobile payments company. So if you get if you look at a barcode on your phone or like a QR code on your phone to pay, that was our idea, except we did that on feature phones uh before iPhone. And this is where I always say, this is where I learned the lesson of being at the right place at the right time by not being at the right place at the right time. Though I think I was the right place, we were in Singapore, but not at the right time. But anyway, by background, I’m an engineer uh and I also have a business degree from Michigan. I went to IT Madras in India and I did a master’s. I was doing a PhD at uh Georgia Tech but I bailed out of a master’s uh in aerospace. So I’m a certifiable rocket scientist, as people say.
Host (Michael): Can can you please stop making the rest of us, you know, look so bad?
Guest (Venkat): No, no, I just I just stumbled onto these things. Although I mean, you’re talking about AI and uh science fiction and my reading and so on. So I mean, uh arguably my thinking about using data and all of these things to for to think about future started off with the foundation series with Asimov, right? And which I read back when I was probably 17, 18, 19, something like that. I don’t remember exactly, which is all about like uh these psycho uh metricians or psycho, I I’ve forgotten the exact name, who use uh data and other things to to forecast, predict the future and they know everything that’s going to happen. And that kind of uh formalism to to understand what’s going on has always appealed to me, right? And which is why I became an engineer. You predict things, you look at things, and you see how things are going to happen. That’s been a a common thread, right? And then and then I went to McKenzie and then at McKenzie, a lot of what work that we do is trying to use data to frame something that’s essentially unknowable to determine parameters of what works and doesn’t work.
Uh about more than a dozen years ago, 13, 14 years ago, when I was thinking about starting, uh I was I was running marketing at uh uh Juniper Networks and we were looking to figure out how to target specific individuals in companies. And that’s when I quit to to start my own uh business. And this is back in 2012, 2013 when the first wave, I mean like this is uh when Imagenet uh solution had happened. And we I felt like we could use a similar thing in using profile data from various sources. But how do you, the problem just essentially came down to like we as human beings, right? You look at one resume and another resume, you know how they are similar or different. How do we do it at scale? That was the uh what we’re trying to solve with AI. And you can look at uh keywords and you can look at uh job titles. But like, let’s, favorite example is looking at like assistant VP or assistant to VP, those are extremely different jobs. But from naive matching of keywords, those are our titles, those are extremely same, right? And that’s the, that’s where we were trying to figure out how do we identify the specific individual because you know you guys are in sales enablement and other things and the problem is always like how do you identify that that one person or the that purchasing team that you can go target, right? That’s what we’re trying to solve.
Host (Michael): This is interesting. You know what, your background is actually very fascinating. You you’re one of those folks who started as an engineer because you’re super curious. You started and you started building yourself too. So you built your company, you sold your company, you stayed in sales and marketing. Now you’re you’re basically leading a team as a CRO. So I’m really curious, like what really kept you in sales for so many years? Like what really, you know, fascinate you or interest, you know, spark your curiosity, if you will, just to make you stay in sales for that long?
Guest (Venkat): So I studied for to be an engineer for seven years between my undergrad and my and my failed PhD and I failed as a master’s and then I started working in the automotive industry and I worked as an engineer for one year and then switched into engineering type roles in sales, right? And I was in a sales thing for uh uh for GE Plastics in the sales organ- organization doing some engineering/sales roles, right? And what I really loved about this is the daily, everyday, every month high of uh of sales, right? And and it’s like and we we at at at GE Plastics back in the day, you if you missed your numbers three periods in a row, you’re fired. And if you make it, you get promoted. And so it was like it it was a, you know, every quarter either you got it done or you did and uh it it was a it’s a daily high or weekly, monthly high. And like when you’re in uh any business roles, right, any normal business roles, you don’t have that kind of like immediate feedback to what you’re doing. And I loved it. And even though I started companies and did a lot of things, and if you start companies, right, essentially everybody in a startup is right, you are in sales, right? And then even though I worked in consulting and which was an extremely rewarding experience on its own, I’ve since then it’s always been in some kind of sales and other role. And I love the the high, the the, and you go talk to a customer and the customer loves what you’re doing. That is like to me, and when I was doing my startup or in my current roles, it’s like when the when you go talk to the customer, the customer loves what you’re doing. That joy of like seeing the light go up in a customer’s eyes, that is joy. It’s like the the joy that you get when you’re talking to your kid and you’re trying to teach a kid something, that’s the joy you get, right? That is the high that I’m chasing. I understand it’s, I shouldn’t be chasing that high, but like that’s what you look for, right? You know what I’m saying?
Host (Michael): You know what, I actually challenge that idea that you shouldn’t. You know why? Because many people try to, you know, make everything about sales a science. Look, I agree sales should be more of a science, otherwise, you know, we cannot scale it. But for individuals, we know we are in a risky business and if we are not risk-takers and part of again taking risk comes with this passion and joy and uncertainty and then when you figure things out, obviously to your point, you get the high, you get that high that, you know, pumps you and said, “Hey, tomorrow is another day, tomorrow is another day.” And then the quarter is done. Okay, everything reset, back to the basics, run. So many people don’t like it. Like, like it’s so funny, I was chatting with a friend of mine, he said, “You guys are insane. I hate sales.” I was like, “Why?” Because you want to be comfortable. So sales make you uncomfortable for good. Again, this is my point of view, but um it sounds like we are sharing, you know, similar sentiments one way or another.
Guest (Venkat): No, absolutely, right? I mean, uh uh so there there is a, by the way, there is a, this is where doing a sales role as a salesperson versus a sales leader is so different, right? And there are very few jobs where where doing the job versus managing the job is so different as in sales, right? And as a sales leader, and this is one of the things that I miss, right? As a CRO, I don’t get to go be in that chase, right, in that everyday thing. I’m going to call you, I’m going to talk to you, I’m going to do this. It I I, you don’t get to be in that and I’m removed. And especially for a company like ours, a lot of things I’ve done where it’s velocity business, I get into things only when shit has hit the ceiling, right? Uh and until then I don’t. And and which is which which makes me miss that those everyday life of like the frontline salesperson uh doing the thing where you’re you’re, you know, you’re the Marines for the company, right? You’re right there telling the story, going there, fighting the good fight. And which is by the way, every time I sign off my team for the past, I don’t know, Lord knows how many years, 15, 20 years, I always sign off by saying, “Keep fighting the good fight,” right? And that is what we as salespeople do. We are the Marines, we are the ones who are the first boots on the ground and we’re fighting the good fight, right? And I and I and and as the leader, it’s like you miss that, but but it’s it’s, and this is where and you know I’m an engineer and so bring in a lot of process thinking and so on. And this is where being in the background does help me and having done the role of a salesperson where like helping them come to that right is is what my role is, right? I see my role as a coach and a and a and a and a cheerleader and a also, you know, there’s always an evaluation component to this, but like like those are the elements that become important to to what I do.
Host (Michael): This reminded me of this, what was the movie, “Creed” or something like, it was like the coach, you know, training the new, you know, new new dude and and it sounds like that. Look, I’ve been inside the ring, you know, I got my trophies, I I learned, I got a bunch of, you know, I don’t know, punches in the face, right? I can help you, at least when you get punched, you know, hopefully you don’t break. So let’s talk, let’s talk about that. When you wanted to get into leadership in a position, have you mentally prepared yourself or a better question would be how actually did you prepare yourself for the role or maybe you didn’t. So tell us, you know, what happened.
Guest (Venkat): So uh when you’re switching from the the person in the front versus switching on to being a leader, sales leadership involves three things, uh uh compensation, coverage, and capabilities. Meaning, what what are you comping your your salespeople on and how do you structure it to coverage, like how many salespeople do you have per area and so on and so forth. And the third thing is capabilities, what skills and capabilities do my team does my team have to deliver on what they need to do. These three things I didn’t think about it when I was a frontline salesperson, right? We as frontline salespeople often, we would resent like spending like back at GE, we would train in Six Sigma and we resent the fact that we took a a a week off or whatever to go do the training, right? However, whether or not Six Sigma helped is specifically is a different issue, but like these kind of training things help, right? And so as the leader, you think about these elements in an extremely different way, right? So as a leader, I’m less thinking about me pitching to a customer as much as making sure that my frontline is telling the same story, is doing the same thing to represent the company, to solve the problems of the customer, which is all that matters at the end of the day. The customer truth is where everything arises anyway. And that is what matters, right? So it’s a flip in terms of like doing things versus getting things done. And as salespeople, we’re always like in the action, we want to be in the thing and we want to go do that. And making that flip to getting things done as opposed to me doing it is a huge change, mhm. Which is why a lot of great salespeople do not become good sales leaders, right? And which is why I mean in some organizations, like, you know, IBM is a great example, Cisco and so on and so forth. A lot of these sales guys, they might become like VPs and so on, but they’re still like managing one uh account and in that account, they might manage $100 million, but they’re not managing a big team, right? Or they might manage influencer, but they’re not like uh uh they’re not they’re not managers in that sense. So so anyway, so when you’re making a transition from the frontline to leader, you’re thinking about how to get shit done as opposed to doing shit. And for that, we control certain levers, right? And again, a lot of people get fixated on compensation. Of course, compensation is important. And then coverage in terms of like number of people that you have is again another thing that people get a lot of us get fixated on. But one thing that I do think is over the past, let’s say four years that I’ve become more fixated on, that’s capabilities, which is like how do we develop the capabilities in the in the team to make them all good, right? So now I’m going to, I don’t know if you want to answer, but I’m just going to go off on a tangent.
So about like four or five years ago, we um implemented this uh tool uh uh group at 8x8 and what we found was that the people who, it helped newer folks and people who are not doing well to scale up and do well. It didn’t help the people who are who are uh already doing well. And the reason being people who are uh who are good and achieving their numbers day in and day out, they already follow the best practices even though they might not have recognized it, they somehow stumbled onto it, right? And the reason I bring this up is that AI, technology, automation, all of these things, I don’t think is this is a big debate that’s going on right now, right? I don’t think is going to make the top guy even better or gal become much better. It’s going to make the long tail achieve numbers faster and make the ramp up of newer AEs and newer things, all of these things faster, right? And and AI can be deployed, AI technology, all of these things can be deployed in multiple ways. You can think of uh uh like sales engagement tools to repeatedly follow up and do that. You can use that or like what we’re doing as Splashtop, you can use ChatGPT and other tools to coach you on how to uh do things. And you guys are of course doing things on that front. So where I’m going with this is like when you make the transition, you you, the big thing for you to stop doing is to think, “Hey, I would have done differently from you.” Of course, of course I would have done differently because I’m, you and I are different people. But like how do I get everybody in my organization to perform at a higher level? That has to do with like how do I get my get my not the best performers to do better. Maybe you can, but it’s to make sure that the long, the the medium and and lower tail gets ramped up faster to at least the average, then the whole thing goes up, right? And so that is how I think about it. And this is where the technology and everything comes into play to improve the capabilities of uh the the the newest person, the least capable person, and ramp them up very quickly to to perform much better than what they could have done otherwise.
Host (Michael): I love this because it sounds like again, you you have a coaching culture yourself as a leader and you bring it to the company by saying, “Hey, look, even I I gave you three topics to talk about. We talk about compensation and hopefully again, your reps are happy with it because that that’s a big topic to really you know open up and talk about.” But then you said even headcount, like many people focus on, you know, headcount right now. “Okay, money was cheap before, we hired a lot, let’s fire a lot, let’s get you know someone else’s B and C players to our company with a hope of, you know, building A players.” And to me, it sounds like that 80-20 dynamic should change because of the fact that again, hiring a lot of people might not be the best strategy. You need curious people who really get their hands dirty with new technology, new ways of doing things. And to me, old playbook doesn’t work and we don’t even have a playbook right now. Even there is no playbook. So the only way is to really make our people perform at their best, whatever that best might be for your organization. Absolutely. Let’s break that down. I’m really curious to hear your process even before AI gets involved for that repetition of practice or coaching. Where do you start? Where do you start your assessment? What steps do you take before implementing anything?
Guest (Venkat): So the biggest thing to do that is starting off with metrics, right? What are you trying to achieve? Of course, we’re all trying to achieve uh meeting our quota and so on and so forth, but that’s at the the higher level, right? So then you put in your usual pipeline and funnel metrics and every stage of the way and and so on and so forth. And once you start doing that, you start getting and so and this is by the way another place where uh I spend a lot of time, uh whether it’s sales and or marketing, in creating what I call as this revenue model, which is like you start off with like end, what’s the revenue you need to get, therefore what is the bookings you need to get, therefore what’s the pipeline you need to create, therefore what are the activities that you need to do. And it’s a it’s a spreadsheet that we create and I’ve created this in various companies over the past 15 years or so. As I always say, “Plans are useless, but planning is critical.” And creating the spreadsheet allows you to think through what you think the world is and then how the world is related to uh this or not, right? So that framework is to me the number one, right? Because that then once you have that in place, then you can understand where where the bottlenecks are, right? And then you can start solving specific issues that we have. So for instance, in in a lot of companies that I’ve been to, I’ve introduced uh uh outbound for a company that’s primarily relied on inbound. And typically, uh any SaaS company that’s primarily relied on inbound that’s going outbound, the sales guys need to be trained, right? Because it’s unfair to expect some salesperson to look at a deal where on the one hand, in inbound, you have someone who’s tried us, which means they probably have tried somebody else and I’ve done everything else and have decided to buy, and then we just need to go through some mechanics around contract and other things versus you go to a place where they don’t know about you, they need to be coached and they need to be talked about this, right? And then how do we, so how do we recognize this problem? We recognize the problem by looking at this end-to-end math I was talking about, which talks about, you know, I talked about it from end onwards, but if you start from beginning, activities to pipeline to what funnel metrics that you have, right? And then you understand where the drop-offs are and then try to help the folks, sales team, on how to solve the specific issues that we have in each of these things. Some of this is with tools, some of this is with training, some of this is, you know, at McKinsey we used to call this like forum and field. Forum is like you have like official classrooms where you coach people and then field is like where you observe what’s going on and then help them with that. And today, you have all of these different tools where we can get data about what people are doing and then make it come back through AI and so on and so forth. Actually, on that front, like, you know, of course, tools like Gong and Chorus and so on and so forth, which have been around for a while. But like what we did was like we, because we use uh uh recordings either on SalesLoft or on Microsoft Teams, we have all the transcripts. We put the transcripts and other things through uh uh ChatGPT and we are able to uh evaluate our people in no time, right? And so we built the equivalent of a Gong in two hours and uh well, and $0, two hours of somebody’s time and and $0 and uh and we could, we could then understand like what is actually going on. So to to to get to give a more crisp answer to what you were talking about, there is the overarching model that we create, that that we think this is how the world happens. You look at the data, look at what the drop-offs are, and then start doing very targeted activities, tools, tools, technology, people, etc. to to go solve those specific issues in terms of where they need to solve. And in the recent past and and not just in in my current company but but in in my previous company, previous two companies, the bigger problem has always been an enablement because you know, companies change, we add new products, we target different things. How do we get our salespeople to to go resonate with that, right? And that’s not uh an easy thing. It’s not just uh me being able to tell the story, it’s the 100, 200 people that need to be able to tell the story, right?
Host (Michael): So and they all have different, you know, skill gaps, they all have different strengths and we don’t even know if they even read the material they receive from marketing. So that look, that that’s a that’s a good expectation, if you will. Look, I have zero expectation that you guys do it. So let’s just put it into practice. No, I’m with you, man. The problem with enablement is very, the fact that it’s very reactive and disjointed. Like marketing do something, hey, do something for me. Okay, CRO has a plan to A/B test something, do something, tell me what you wanted to say something.
Guest (Venkat): So this is the the the thing here, right? I think the big thing is um a lot of the sales enablement tools uh are perceived by AEs as being evaluated, right? Because because you have stuff on these various tools and then you and then we we have RevOps running it and then we always are like, “Dude, uh uh uh,” and we as sales management go to them and say, “Dude, you didn’t do this training, you didn’t do that training.” I’m like a school mom looking at telling people all the fucking things they didn’t do, right? The difference is, and and this is the lesson I’ve learned, especially in the past year or so, we just as we need to help the customer make their decision uh to to buy our product, we need to help, we as sales leaders need to help the sales folks do the right thing. I believe, and this I fundamentally believe, each of us as individuals, as human beings, want to do the right thing. We just don’t know how to do the right thing and we’re worried about the consequences of not doing the right thing or being perceived as not doing the right thing, right? And so the challenge then becomes how do you get your sales guys to take the, so to to to do all of these things that that I’m saying, “Oh, you as a school, I’m the school mom and you got to do it,” right? Instead of that, you pivoted to saying, “Okay, how can I help you do your job?” right? And I give you these tools to get you to do the job. And by the way, even if you uh uh had followed the old command and control structure where you’re, I’m telling you what to do and you do it, at some point, you’ll get there, but it’s a far better adoption to to help the AEs recognize why they need to do what what we’re coaching them to do as opposed to me saying, “Dude, you haven’t filled this out.” Which by the way, don’t get me wrong, I have used compensation as a way to get people to do all of these courses, but that’s not the only way, right? It’s it’s it’s the combination of that with helping them to recognize why all of these things are good things and then helping them with going through that, if that makes sense.
Host (Michael): This is this is such a relevant topic to talk about, like adoption, because everybody wants to, you know, get a piece of the new thing. I want to implement AI. Someone like you, you know, you’re more hands-on, you build your own, you know, GPT and give access to your reps and evaluate them. Someone else buy a product, someone else do the mix. But the most important thing is if your end user doesn’t see value in this, you’re just wasting your time. And I’ve seen this even with some of our own clients and we learned a lot, you know, about like adoption while doing this practice is that I come and, you know, push my people to use this. At the beginning, it might actually help because if people don’t try something because they’re burnt by all the tools that you throw at them, it didn’t work out. It might help if they see the value behind that tool. They are very difficult because as salespeople, former sales, another tool, Jesus Christ, let me do my job.
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Host (Michael): Another point is that to your point, incentives could help, but to really keep this long-term going, they need to see they’re improving something. Either I’m booking more meetings if I’m, you know, SDR/BDR or I’m, you know, closing faster, larger deals or I don’t think tap on a shoulder or saying, “Hey buddy, you’re doing your job, that’s why I don’t micromanage you” with help. Tell me about this because this is very, very important for people that are listening to this. How do you get adoption beyond incentive and force?
Guest (Venkat): So let me illustrate this with an example. Some 20 years ago, I was doing a, I was doing a um consulting engagement with a firm for a for a large telco. And this was a telco which is uh, this is a call center. And um now, so we were dealing with a team of 10 or 11 or 12, I don’t know the exact number. And each of these guys, right, it’s, and we were coming up with the with the with the uh training curriculum that’s going to be rolled out to everybody, right? And so these 10 or 11 people, they have zero concept of uh and and and me too, like what’s going to work and what’s not, right? And uh and for these 10 or 12 people, it’s this affects their uh income, it affects their paycheck, right? So so how do you get them to engage in that, right? In the beginning, it was a lot of one-on-one conversations with people in trying to understand it. And then I would be on a call, I would sit next to them on a call, and then I would be like, they’d be, they’d do something and then be like, “Now ask this question,” right? And then they would ask this question. And initially, it was like that one-on-one interaction, giving them the the the the, first of all, the safety net that even if you fail, it’s okay, but consequently giving them permission to try different things and see what works, right? So it’s that, it’s that combination of like on the one hand, well, they still needed to make their paychecks and then the on the other hand, we need to get them to try different things to do it, right? Because, you know, look, when I was a sales guy, there was like uh maybe like two or three hooks that I had, right, where I would always go back to. If you did this, that gas is like more like, you know, if you had to use it for this particular application or if you’re going to put plastic in your engine, it means we’re super hot and you can use our Ultem and blah, blah, blah, right? We had, I had these things based on what the uh uh use case was. But like I recognize now or even beyond that, like it’s beyond those four, five, six things, right, or three things or two things that I, let’s be honest, one to three things that I did and getting them to try these new things and then once we succeed, reinforcing that success and moving beyond, those are the things that we needed to do to get that buy-in, right? And this particular thing, it worked out really well and then they rolled it out to everybody uh uh in that whole telco for a while. And this started with one-on-one discussions, one-on-one coaching, like, you know, just listening in on the calls and being there for them. And they also knew that hey, if things were to fail, I’m there to catch them, right? And that I think matters more for anything because we as salespeople and this was at least, this is how I felt when I was frontline in the in the teams back in the day, you feel like you’re alone, right? You’re out there. Yeah, you have a a company so, but you are the one who’s representing the whole company, right? And this is another thing that I think we as leaders need to reinforce with our salespeople, which is that it’s not just you do that, it’s the whole company is behind you, right? Yes, you are the Marines, you are the guys who are landing on the beach, but we have this whole army, this whole country, whole thing behind you to support you in whatever you’re doing. And that getting that level of comfort and coaching them on other things is through the organization. That’s those are the challenges that we have to do as leaders.
Host (Michael): Look, and without it, to your point, it’s impossible to get anyone to do anything. And I was up to, “Hey, we just rolled this out, please do it.” And I was one of those folks hitting my number and I’m like, “You know what, I know you’re not going to give me shit because I bring my number, so I’m safe.” Poor guys that have to go through all this like two hours training in a group of 30, you know, people sitting and nobody wants to get schooled. I think people really want to learn how to be better, how to do better. And those one-on-one conversations, building that safe environment, giving them at least something to start because you said it earlier, people want to do their best but sometimes they’re loud.
Guest (Venkat): That’s the key, that’s the key, right? And here’s the, here’s the difference, right? And and this is one point that I want, I’m want to make sure that we get across. When you’re in sales, like who doesn’t want to make money? So everybody wants to do well and everybody wants to succeed. However, bigger uh motivation in life is failure avoidance than success. If you get caught by a lion, you’re going to die. If you fail to go catch the zebra to eat, that’s okay, you’re going to get your meal next day, whatever, or go read a route or whatever the case may be. The fa- so this this thing where we have this pain avoidance or failure avoidance or any of those things is far more overwhelming than our desire to succeed, right? So this is where we say, “Okay, how do we then create a uh a safe environment where in the realm of coaching and training people and so on and so forth, we make it in a in an environment where people don’t feel the the uh evaluative nature of of coaching, but like they feel that it’s actually something that is going to help them, right?” So they they can avoid the pain and then hopefully figure out how to succeed.
Host (Michael): Makes sense. Like to me, this sounds like it’s beyond just winning because if if you sell that vision that, “Hey, you’re going to win, you’re going to do better if you do this,” it actually sounds like school again, back in school, if you do this, hopefully you become a doctor, if you do this, like you can make a lot of money or a better life. Instead of that, you can say, “Hey, um this is what I’m noticing, these are the problems that I’m noticing that you might be, you know, facing. You know what, let’s just cut the crap. Is it safe to say if we actually, you know, help them to avoid a future pain, they might actually, you know, adopt to such a thing better?”
Guest (Venkat): Absolutely. The desire to avoid a future pain uh or even a present pain uh or slightly depends on how long in the future is uh will be as long as you can demonstrate a clear tie uh then it can work. However, here’s the thing, right? So for instance, working out when you’re a young person, you say, “Hey, um you got to work out now because otherwise, you, if you work out now, you can avoid a heart attack when you’re in your 50s,” right? Uh but it like, “You can avoid your heart attack when you’re in 50s,” it’s very hard for me to get motivated with that in my 20s. Yeah, so it depends on how far in the future you’re talking about, right? On the other hand, to me, you say now, “VCAT, you got to work out, otherwise you’re going to get a heart attack.”
Host (Michael): So let let me ask you something. I think I don’t know if you have the answer, but I want to be, you know, nosy and ask you, you want to build a safe environment, you want to get in a room with, you know, these individuals and say, “Hey, this is this is about you. I want to learn about you, I want to help you.” And if you’re just, let’s say selling this idea of future pain avoidance, how should we build this balance so they don’t freak out? Like I I I genuinely like, curious like your conversation, just imagine I’m a rep or a CRO, what are you going to tell me like why why the hell do I need to go role-play with AI? Why do I need to get my coaching with AI, Cat? Like what’s what would happen if I don’t, beyond that you are my boss?
Guest (Venkat): Well, actually, I mean like on that front, like if people were to do it, do something just because I’m their boss, then I’ve lost the game, right? Because it’s not, it’s not going to sustain. So I’ll just illustrate what we have done even in my uh current role. It is um um so uh uh uh as a part of our uh overall uh coaching rollout, initially we had it as like a, using AI as I was talking about earlier, as a Gong evaluate, right? Use use AI to evaluate people and then that told us, “Hey, we need to coach people.” And then initially we we had a coaching is like, “Okay, we use uh AI to do role-plays.” And then we said, “Okay, we’ll use AI to to help you craft your stories and so on,” right? And so this is where I think in my mind at least, I made a shift, which is to go from this evaluative thing of like, “Hey, you’ve done wrong,” to then make a transition to then say, “Okay, I’m giving you the tools to go succeed,” right? And when you make that flip to an evaluation to saying, “Okay, I’m going to make, I’m doing all of this to make you succeed,” it becomes a big diff- there’s a huge difference there, right? And so I’m seeing now where people are like, I’ve started using now, a lot of people don’t recognize these different elements of ChatGPT that we have deployed, but we’ve helped them. For instance, we created prompts to help them do research for uh uh for their prospects and and customers, right? And that’s cut down time for a lot of people. So then they say, “Well, okay, so this attributed thing that you’re making me do has helped me save half hour before each call,” right? And for a lot of other people who were not doing it, they’re like, “Hey, I have all of these things in there that I don’t need to do.” So so once they perceive this is starting to help them, that’s when you get the engagement, right? Not because, of course, they will start engaging in the beginning because I’m telling you to do it, but once you start seeing the benefits, then you say, “Hey, this works.” And then you go tell your buddy sitting next to you saying, “Hey, I tried this, this works.” Because we all learn from each other and that’s how the propagation happens, right? So it’s going again, like my thing is always, not always, like the past one year or so has gone from like being evaluative and talking about like how we fuck up to then saying, “How do I help you become succeed and then demonstrate your success,” that’s or demonstrate how you can be successful and then you experience that, that’s where the the the the the big thing is, right?
Host (Michael): I love this. Look, this um reminds me of um the domino effect. A good friend of mine on the podcast actually, Grand Pitches, you know, kind of like taught me this. So you pick a few reps, up-and-coming ones, the ones that are hungry and they want to do better. And then you give them something new, could be your prompt for anything. When they get, you know, some result and you keep pushing to, you know, make sure that they applied in real life, you build your case and then you shoot it straight to the CRO, for example, say, “This manager, these three teamed up with enablement or whoever, rolled out this program, they got a great result.” So everybody wants to be like them. But even more importantly, like that, maybe you artificially build that environment. I love the fact that you said, you know, people talk to each other, your early adopters are your reps. If one person even see value in this, maybe he tells two, three other people and then it has this, you know, snowball effect. And even if it doesn’t pick up, you learn something that, “Okay, this doesn’t work out for my organization for whatever the hell reason.” You either dig in or you, you know, pivot and try to introduce other concepts. Look, I know we are almost about time. I have three quick questions for you, almost two, yeah, quick answers. So finish this sentence for me: “Sales leaders would be 10x more effective if they just…”
Guest (Venkat): …trusted their sales reps.
Host (Michael): I love that. What’s uh what was your most painful sales loss and what did you, what did it teach you?
Guest (Venkat): There’s not a short answer, but my pain, most painful sales losses are times where uh where we were the solution, but but we didn’t explain it to our customers.
Host (Michael): The name of our company is Sell Me This Pen, and many people actually hate that and many love it. I don’t know which one you are, but many challenge that, “Okay, pen is too old to sell these days, so this is not the best question to ask when you walk through the interview process.” So just imagine you can change “pen” to anything, what should we be selling? And maybe you just complete this sentence, “Sell me this…” what?
Guest (Venkat): Actually, “Sell me the pen,” “this pen” is actually not a bad thing, right? Because I’ll tell you why. By the way, SMTP, I used to be in networking and SMTP in in uh in networking is an extremely different thing. Uh uh uh the reason why I think to me SMTP or “sell me this pen” makes sense is this thing where any sales interview you go, it’s like, “Oh, sell me this ball or pen or whatever the case may be.” And it we’ve all been there, right? I mean, years ago, I literally was in an interview where I think it was with Microsoft where they asked me to say, where the the interviewer was saying, “Okay, sell me this pen.” And I don’t know whether I sold it to her or not, but uh uh but like it’s something that we all recognize, right? And so Ashley, I don’t think you should change it.
Host (Michael): All right, there you go. All right, last question. I have a very seasoned enabler next week on the on the show and his name is Lawrence O’Connor. I don’t know if you’ve seen, you know, on LinkedIn, but we share a lot of great stuff. Do you have any questions for him so I can ask him?
Guest (Venkat): Actually, yes. How do we, how does, this is a very broad question, like how does Lawrence O’Connell think about AI affecting sales enablement, right? So the the the traditional form on sales enablement used to be like, you know, giving you the right PDF or or PowerPoint at the right time. Now it’s, it can be more tailored and like uh I think sales enablement now needs to morph into a place where I truly enable the salesperson, right? So if I’m going to take a meeting with Michael, what should my pitch be? And this is some of the things that we’ve implemented in charge, like what should my pitch be, what is the hook, what’s the deck, what’s, I mean, so these are all things that we need to do and I think AI can do help you do all of these things, right? So yes, the question is like how do we see this evolve, right, with AI and other things? And uh the whole old Highspot way of, knowing spot, but like whole Highspot way of uh providing the right card at the right time, while it was appropriate at that time, it we’re past that, right? And how do we change that is where where I think we need to go.
Host (Michael): This is a great question. I think we can even start a conversation with Lawrence next week on this one. Look, I appreciate you. I I love this conversation, a lot left. Um if someone wants to reach out, can they, can help?
Guest (Venkat): So you can uh follow me on LinkedIn, uh uh uh Venkat Nagaswami uh or LinkedIn/ardwami.
Host (Michael): We will include it, yeah.
Guest (Venkat): And then Twitter, I’m on Ward Nagaswami and I think uh a single word. Um and I’m on Blue Sky, the same Ward Nagaswami. Those are the places where I hang out, Blue Sky more than Twitter anymore or X, I should say.
Host (Michael): Yep. Yeah. All right, amazing. Thank you very much. I like the conversation and uh until next time, bye now.
Guest (Venkat): Likewise, brother, cheers.
Confidence: 100%