Why Buyer Enablement Beats Sales Enablement with Rory Sadler

it's not what you can build anymore. It's when you can build it, how fast. And I think that's the same with IP as well. Like you can hesitate and be cautious, but you're going to kick yourself and you'll end up being the next Kodak. Hey everyone, welcome back to Make It Happen Mondays, where we talk about sales, business, entrepreneurship, personal growth, mental health, and everything in between with guests who I truly respect and I think make a positive impact on the world around us. Now, today's conversation is with Rory Sandler. He's the co-founder and CEO of Trumpet. He spent years in the world of SaaS sales as an individual contributor and then leading global teams at companies like Hotjar, where he experienced firsthand how overly complex buying software was and the importance of creating a seamless buying experience.

This led him to build Trumpet in 2021, which is now the category leading digital sales room, helping companies like Gong, HubSpot, and Personio increase their sales velocity. This is a fun conversation. He's got a really interesting background as a kid. Started selling stuff, suites at school and DJ business and had a few jobs in hospitality. And then he went into business and entrepreneurship. And I think one of the reasons was because he just had that in his DNA. I mean, he grew up with a single mom and a few other things. So he quickly, you know, I think one of the things that struck me was why he started Trumpet. And obviously the challenges that sales has today, it's so disjointed. Customers need so much help making this decision.

You have a million internal, you know, people that you have to communicate with, right? And coordinate to get them all on the same page. And doing that through email and calls and everything else is just not fun. So we talked about his aha moment of like when that really struck him of why he wanted to start it. And then also the difference between entrepreneurship and just being part of a startup. And a lot of kids these days, oh, I want to be an entrepreneur and they start, you know, they join a startup company. It's not exactly being an entrepreneur. You get a higher risk profile than most, but an entrepreneur is that one who starts the business and takes that initial risk. And there's a big difference with that.

And then he talked a lot about the buyer enablement instead of sales enablement, the buyer enablement, helping them buy, which I'm a huge believer of and the mutual action plans and how to use them. And I've always appreciated mutual action plans, but I've never really used them strategically myself. I use a little bit of a different version that we got into. And then obviously we talked about personalization in a few ways. So, um, this was an interesting conversation because I think it's that good balance of sales, technology, buyer, and where we're headed right now. So I hope you enjoy this conversation as much as I did. Let's make it happen. Rory Sadler, welcome to the Make It Happen Monday podcast, my friend.

How are you doing today? I'm all good. Delighted to be here. Thanks for having me. Yeah. Thanks for joining us. It's going to be a fun conversation. Where are you actually calling in from again? Accent gives it away. London, UK is in, you're in London though, right? Yes. Yeah. All right, cool. So let's, uh, let's chat like as always, I mean, for the audience here, we're going to talk about the drastic shift over the years, especially recently of, of, of seller centric versus buyer centric and how much power the buyer has right now. Um, uh, but before we do that, Rory, I always love to talk about kind of origin stories here, man. And I did some digging and you got some, you got some interesting stuff here that I'd love to dive into as far as, but I do want to know like the stuff I can't find on LinkedIn, right?

Like where you grew up, parents kind of where you got that entrepreneurial itch, if you will. You know, I, I, I heard you sold some sweets at school. You had a DJ business. You did some cool stuff. So walk us through that and then, and then we'll go to college and then we'll go from there if that's cool. You've come deeper than some of my team are aware of. I'm impressed. Well, they hate the power of AI, man. I could do, I could do research now in a second. It doesn't even take it. It doesn't even take too much time for me to figure this out, but I always love the DJ thing is always fun to me because, you know, I grew up in the clubs and stuff like that. So, uh, love to hear a little bit about that.

So talk to us about where you're coming from, man. Yeah. So I was born in the North of England, but raised in London, uh, parents split up early. So then I kind of grew up with your single mom, raising three kids, that kind of whole story, saw the struggle, uh, saw other kids, uh, you know, living a life sometimes I wanted to have and that kind of thing. And then wanted to provide for mom seeing those struggles. So I think that's like deep down where a lot of that drive comes from is, you know, wanting to create security for family and wanting to provide for my family and future and so forth. So that was always like curious, were the oldest, youngest, middle son, like where were you on the, on the, of the three kids?

Middle. Yeah. So first son. So then kind of took on that, like, responsibility, like being the kind of man in the house and all that jazz. Um, so yeah, from just a very early age had like the awareness of how money could create security. And like, there wasn't a lot of that in our household. So from a very young age was trying to sell, you know, lemonade down the street was trying, you know, doing, uh, these kinds of gigs at school. Like I ran a poker club that got shut down super quick, as you might imagine. I didn't even know how to play poker. I just provided the space and the cards and everything. Um, yeah, sweets. That was a good one. Drinks, uh, DJing was very lucrative, put another parent out of business because just took over, uh, all of the, all of the gigs.

And, and then, yeah, that led to university where I studied it. If you can believe that there is a subject on entrepreneurship, but there was just always this curiosity, this drive of, um, yeah, kind of building something from nothing. And, um, uh, you know, I think the more you get into entrepreneurship, as you know, I think the commercial aspect starts to fade away. And then you, you know, you have like a deeper wire and a deeper understanding of like, why would you go on this absolutely insane, crazy journey that is exhausting, but equally so rewarding. And I think, yeah, I've definitely, um, seen that in the, in the last few years with trumpet. Yeah. I think it's funny because, you know, people say like, you know, I want to be an entrepreneur.

I'm like, you sure about that? And, and by the way, entrepreneur, I think a lot of people think like being in a startup is an entrepreneur, but I like, they're like, Oh, I want to join a startup and be an entrepreneur. I'm like, Hmm, there's a difference. The entrepreneur is the one who takes a hundred percent of the risk, starts the company and goes from there. The person who joins fourth, fifth, sixth person is a risk taker, but they're not necessarily an entrepreneur. They just like startup net vibe. And I, and I kind of categorize that because I actually fundamentally don't consider myself an entrepreneur because I never really stopped, created something and then went all in on building the company around it.

I kind of evolved into it. And I've always said, I'm kind of a calculated risk taker where a couple of pieces need to be in place before me to take that jump. Whereas my other friends, entrepreneurs are like the straight up risk takers, like fuck it. I'm doing it. I'm going all in. And, and it's like, all right. And I think there's a difference and people conflate the two. Do you see, you see people kind of having this, uh, kind of vision of entrepreneurship that is a little bit skewed, uh, compared to what, you know? Yeah. The common trend is I want to be my own boss. I want to make life-changing money and everything. And it's like, you know, how often does that really happen? And are you your own boss?

Like, you know, you, your customers become your boss, your investors become your boss, all those kinds of things. So it is your life changes overnight. It's 24 seven, you know, you're accountable to a lot of people and your team and everything like that. So there's a lot of trade-offs that you need to make. And I think people aren't always fully aware and they're like, yeah, yeah, I'll be fine with all of that. But actually in practice, it is, you know, it, it, as I mentioned that it is incredibly rewarding and it is worth every second of it, but life-changing in terms of the sacrifice you have to make with family, with friends, with time, with your, you know, your own health at some points and everything like that.

But, um, I, you know, at one point I got told that I would end up being an entrepreneur, which I'd never heard before. And that was like an innovator within a company. They were like, oh, maybe you won't take enough risk to be an entrepreneur one day. Um, but you know, there are very successful people who joins it, you know, day zero, they take DocuSign to public and, you know, they were behind the scenes. And there's a lot of people like that out there. And I think there is a world where if you really put aside titles and your own ego and you just want to be relentless at building something, I think there's a lot of opportunity that comes with that. And you can have that freedom, which comes with early stage startups to be pivotal in its growth.

Yeah. But yeah, it's a, it's a different mindset and it's a different level of risk. There's a bit of a net there. Hey, I hope you're enjoying the conversation so far. I want to take a quick minute to share with you what I'm working on these days with my new JB sales membership. It includes live monthly training delivered by me on my two signature courses, which are filling the funnel and driving a close that cover all aspects of the sales process. It also includes monthly workshops that will be running on specific sales skills and different tech skills like ChatGVT and how to leverage AI throughout the entire sales process. Finally, the membership gives you access to my entire online catalog with every course and every tip I've ever done.

And as an exclusive offer to my podcast listeners, if you go to jbarrows.com, click on the individual membership link and use coupon code podcast at checkout, you'll get 25% off. Now let's get back to the conversation. Yeah, exactly. A little bit again, kind of calculated risk taker. And I think that's, you know, a lot of the warning that I got was don't like when you go into jump, you know, for your business for yourself. Um, make sure you don't work for yourself in the sense that yes, your customers are your boss and all this. But a lot of times people jump into this and all of a sudden they now have a job, but the job is the company. So they are working for their company. They are not working as their company.

If you know, like working on the business in the business type of thing. And now you have like the worst case scenario in the sense that you have a boss, which is you, but you are doing the job of 50 other people, you know, the finance, the operations and all that other stuff. And so you end up working for yourself, but in a different context than working for yourself. And that's a nightmare scenario where people find out. That's why I recommend everybody read the book, you know, e-myth or e-myth revisited that the entrepreneurial myth, because it is a fact about how, you know, people glorify it as, as glorious, but then they get into it and they realize actually, they don't do 90% of what they love doing.

Right. And you have to believe, and I think this gets into our conversation, right? Cause I, I, there was a turning point for you, obviously, right? You, you worked at hot jar and, and you kind of other in a few other SaaS roles. And it says, you know, you kind of experienced firsthand that the complexity of SaaS selling and what, so what was the, walk us through that job and kind of what you did, but also where was the aha moment where you were like, wait a minute, there's a massive problem here. And I I'm passionate enough about it to go off and do my own thing right now to fix this problem. Yeah. I think like most salespeople, I fell into sales without realizing it. Yeah. I was just so desperate to, to get into startups and see how do you build these things?

I want to see behind the scenes. My first sales role was, you know, in at seven, leave at seven on the phones all day, you know, manually dialing, no power dialers. It was manual phone entry, all that kind of stuff. Anyway. And then before I knew it, I kind of blinked and spent nearly eight years in the world of sales as an IC growing into a team lead. And what I eventually ended up experiencing was working for a bootstrapped company versus a lot of venture backed, high growth, you know, features left, right, and center integrations that we can never keep up with was, you know, how do you keep your team motivated? How do you still win when you can't compete on product and, and, you know, especially when it goes feature to feature.

And when we looked at the business, it had such community around it, advocacy for how easy it was to use, uh, easy to get started, the ease of like, um, the, the kind of speed of value in terms of what the solution offered. And we thought, well, how do we reflect that in our sales process? And what if we make it really easy for our buyers to evaluate, you know, uh, our solution? And we focused on centralizing all of the overwhelming amount of information. Cause there was a lot, you know, it's very like hot jobs in the web tracking space. So security was a hot topic, all that jazz. So, you know, demo recallings, proposals, comparisons, the deck, it was a bit overwhelming. And when someone's evaluating three, four, five different vendors, which they always were because it was a very competitive space, we wanted to make it easy for them to get up to speed, to be able to share internally exactly why we were the right solution and so forth.

Everything got put into a Google drive link, super manual team hates it, but the results spoke for themselves. So we instantly started seeing that we were winning deals based on the buying experience and we weren't worried about features or integrations anymore. And that's ultimately where the light bulb happened. What if we could make it this easy for every buyer to buy? Cause that was an important lesson for me at Hotjar. It was a PLG product. You know, they didn't have a sales team for years. So it was all about, you know, the small customers and then we were moving up market and the founder there, you know, he loved the small customers. It got them to where they were. And a lot of people will always say, you know, there's a difference between the small guys and the big guys and the, you know, the, the deals that move the needle.

And there definitely is, but we, you know, that the premise for Trump, it was ultimately like, it's often the small guys that will shout loudest about you. So how does every buyer get a seamless experience? And not just in the sales process, started to think it kind of beyond that. So that's where the idea for Trumpet came from. But equally that space that I was in was all about what we call behavior analytics, getting data on your website. Where do people spend time? Where don't they spend time? Does this button work? Does it not like, you know, going much deeper. And I started to think, well, all we rely on in sales is our deck, our sales deck. And everyone gets that copy paste, same thing time and time again.

What if I could start to tell customers and companies, here's how your buying journey is performing. Here's what's working. Here's what isn't. Here's where people interact. Here's where they don't interact and make the buying journey more collaborative and interactive. So it was all of these kinds of pieces together. And it's funny how, yeah, kind of everything came together, but yeah, now fortunate to be where we are with Trumpet and the team that we have. So yeah, it came from firsthand experience in the world of sales, you know, I'm very passionate about the world of sales and glad that I had the career that I did in it, but I didn't ever expect I'd be building for it. But it is incredibly rewarding to be able to get back.

Yeah. And I think, so I'm curious on this, on your perspective on sales right now and the sales rep and the evolution of this role, because it is evolving fast. And I'm quite worried, quite frankly, because, you know, we talk a lot, obviously about how we've switched from a seller centric to a buyer centric, right? They have all the power at this point. I mean, we can go back to the internet, right? If you want to kind of look at sales methodologies, if you will, I think, you know, Xerox came out with solution selling back in the late seventies, early eighties, which was the concept of, you know, just asking questions, holy shit, right? Because before that, we had all the power, clients didn't even know what we had to offer.

So we could legitimately show up and be like, Hey, I'm going to run through my entire pitch deck here because you've never seen something like this before. I'm going to blow your mind, right? And then Xerox came out with solution. All right, let's ask some questions. But then the internet kind of hit and put a lot of the power into the client's hands. And now with AI, it's, it's insane because I tell any rep that doesn't think they're in trouble right now, uh, just go in to pick your AI chat GPT. I don't care. And pretend like you're a customer, right? So again, for me, I'd be like, Hey, uh, you know, I'm a VP of sales of marketing at a 50 person sales team with 20 SDRs, 38 E's. I'm looking at the JV sales sales training for some training on prospecting.

Like, tell me what I need to know. How does he compare it? And when you realize in, in five minutes, you get more value out of, you know, some kid who's going to ask you bad questions, you realize how much trouble we're in. And so with your experience with PLG, right, the client has never wanted to be sold. Nobody ever, you know, you're all here. I hate being sold, but I love to buy right type of thing. I used to kind of think that sales reps didn't need to know the product all that well. They needed to know enough to bring the, you know, to, to be able to pull the right pieces in place, but they were more the quarterback of the solution. Now I, I kind of, I'm flipping my opinion on that because I think we almost need to be product experts.

We almost need to be customer success to guide people through the buying process, not trying to sell them or learn some technique to tie them down on a close or whatever it is. So how drastic is this shift right now? And how, how archaic is our current sales model as it sits today with predictable revenue and the segmentation of roles and the whole ugly process that we go through right now. You mentioned the word drastic, and I don't think there could be a better word for it. And that's not me just, you know, kind of jumping on it, given the space we're in. But ultimately, I think since the pandemic, how we buy has completely shifted. We're all more asynchronous than ever. A lot of people are more remote than, than we've ever experienced before.

And as a result, our time is more precious than ever. We're on back-to-back calls, zoom calls, whatever it is, uh, day and night. And with that motion, you're seeing buying committees getting much, much bigger. Indecision continues to be the number one reason deals fall through and that's on the rise. Sales cycles are increasing and it's because ultimately buyers are overwhelmed. But with that, I think it also subconsciously comes from our experience as a consumer. I don't know about you, but like, I love being a consumer these days. It's like, I don't love buying things all the time, but when I do it, it's so easy. Like the next day, how it arrives, uh, flexible payment terms. You can just instantly click review, compare, like it doesn't, yeah, just, it doesn't matter what purchase you make, you know, Tesla's, that's like a, as easy as buying a book on Amazon.

I did that 10 years ago. Literally the first time Tesla came out, I bought an $80,000 car online. And I, I legit, my experience with the, I was, this was when you could kind of choose the different models of, um, of, of battery, right? So you could get this battery, this battery. So it was a lot more customizable actually when they first started. And so I remember kind of getting to a point where I was a little confused. And so I called the sales line of, right. And I get on the phone with the sales are, but I was asking some, and all I hear is click, click, click, click, click. And I go, Hey, can I ask, are you on the same website I am right now? And he's like, yeah, I'm like, okay. So you're looking at the exact same thing as I am with the descriptions and he's like, yeah, I go, okay.

I got to ask them what, what value do you bring to this equation? And to his credit, he goes, none. Matter of fact, he's like, I'm just here. If you want to talk to somebody, he's like, I, you know, all the answers are right here. I'm just kind of walking you through it. And I'm like, holy shit. And again, I bought an $80,000 B2C product online without going into the shop or anything like that. And it's, it is. And that was 10 years ago. Yeah. And that threshold in B2B is like, you know, it's, it's increasing. And so yeah, as consumers, that ease is what we want subconsciously. And it doesn't happen because we get forced into a sales process that's being guided around the stages in the pipeline.

And yeah, Bant comes in and we've got our qualification questions and so forth. So, you know, but what I think is happening is because of the rise of vendors, the number of vendors in each space is overwhelming. There's like analysis paralysis. But what we're noticing is buyers will lean towards the one where they can get the information, whether it's pricing, integrations, anything like that, or a demo, the quickest, anyone that makes it tricky creates friction. No one's got time for that. No one's got time to wait and follow up. They need information now. We're all very busy. We don't like our day job is not purchasing software, but from procurement, like, you know, if we've got a problem, we're going to try and find a solution.

We'd have time to like actively and kind of deeply investigate five plus vendors in that traditional method. We are all busier than ever because the expectations are higher in the world of B2B. You know, we've got AI pressure from our leadership asking, how are we adopting it? And we've got to go, go, go. And we've got more systems and notifications kind of coming across our screen. So the world of B2B is relatively overwhelming. But I think when you think of buying software, the expectation is shifting faster than most of us can keep up with. But it almost begs the question of why have we made it this hard? Why have we not thought about the buyer and put them at the center of the experience?

Uh, I know why it's because predictable revenue came out. They, I mean, I'm straight up. I, I, I think, you know, COVID just, I think exacerbated the problem. I actually think the advent of predictable revenue, I, I personally think it, it ruined sales because I mean, I'm way older than you are, right? I'm creeping up on 50 at this point. And I were, you know, you talked about making, you know, manual dials, man. Like that was all I had. I, I had like, you know, a printout of the yellow pages and I was, you know, banging the phones. There was no CRM or any of that stuff, but I was a full cycle sales rep. I understood the business. I could have every conversation. I could prospect, I could close, I could even account manage.

And I had my territory, my book of business, and I managed that to get more cross sell, upsell and everything. So I knew my customers, I knew my product, I knew everything. And yeah, it was a lot harder, um, kind of to get into sales back then, because I think there was a stat that I read a long time ago that three out of four people that got in, got out because it was like, Holy shit, I can't do all this stuff. And the segmentation of roles allowed it to be a lot easier. It's like, okay, this is your job. You just make cold calls. That's it. Right. Um, but the problem is you couple that with, you know, 2010 ish when just money was free, grow at all costs. And there was, it was great for us.

It was great for the, for, for us as sales organizations, because we scale rapidly and what, but it was never buyer centric ever. Nobody wants to be handed off five times before they actually talk to somebody who knows what the fuck they're talking about. But the client tolerated it because money was free, grow at all costs, ROI didn't matter and money was everywhere. So I was like, yeah, fuck it. You know what? I want gong and sales loft because, you know, even though they're kind of similar gongs, call recording is better and sales loft got a better platform. So fuck it. Let's get them both. Right. Let's, let's go, go, go, go, go. And yeah, okay. I got to deal with these little shitty sales reps just to get to somebody who I know what to talk about.

But that was, I think just the expectation. But to your point, we've now all grown up more and more and more with the expectation of as soon as I want it, I got it. As soon as I have an, as soon as I have a question, I have an answer for it. So that's where I think that I'm actually presenting. You're part of pavilion, right? You're part of the pavilion crew. I don't know if you're, you're not there obviously, but I'm, I'm speaking this week in DC and it's called anything but predictable. And it's how this model has fucked everything up. And no, get me wrong. I've made a shitload of money off of this model. Like I'm not, I like I'm a, I'm a huge offender of, of perpetuating the problem. But getting back to where we are today of all the friction we've added to the process, where do you see the highest level of friction, right?

So let's start there. Like, like, you know, from the cold call to the discovery call, to the demo, to the SE, to the, where in your experience, does it fall down the most? I think it'd be easy to say, you know, discovery call that's filled with boilerplate questions and they don't see any of the product. And, you know, HubSpot stat, like 50% of buyers want to see a product on the first call. I think it's a hundred percent. I think we all want to see something on the first call, but like, I think that's the easy answer. I actually think it's the, still the lack of personalization throughout the, the, the kind of buying experience. And when I, what I mean by personalization is, you know, tailoring messaging to each persona, building, you know, execs, not even an exec summary, a summary for the different stakeholders that are brought into the conversation as it develops, sharing the right and relevant content at the right time that they care about, understanding not just who you're speaking to, their product, their customers, their business pains, which, you know, you and I know is like, boy, like super standard stuff, but just going on to every call being like, Hey, this is what we do.

These are the typical questions I ask. It's just like lazy selling gets lazy answers, as they say. So I think, um, there is still a huge lack of personalization, but I think at the same time, the shift we're seeing should enable much more personalization because now our job as sellers is less kind of transactional, you know, uh, shifting, um, what's on the shelves into getting deep into understanding our customer and how we can help them, which again, sounds like not rocket science to you and I, but it's finally like, yeah, we're, we're finding a point where it feels like it's going to become the norm. It has to be. And, and I, and I dread it's, you know, I still do trainings right now just to, and I show very basic AI stuff, right?

Just because I don't believe in automation with AI. I believe in augmentation. And, and so I, none of my GPTs will give you the answer, right? It'll help you get the answer, but it'll educate you along the way. And I do some basic stuff just like, Hey, let me show you how I created this GPT and how I prepare for a meeting. I started the industry. Then I go to the company and I put their 10 K in there and that. And when I saw that, like, people are like, Holy shit, man, like this is insane. I'm like, how have you not, especially in the SAS and the tech world, like I could understand in other industries, whatever, but in the SAS and the tech world, if you are not, I ask people like a scale of one to 10, when I do my trainings, where are you with AI?

Like one is you're barely touching it. Five is you're using it every day. You're customizing everything. And inevitably I get threes and fours, right? A lot of, well, yeah, I'm pretty good at it. Then I show the bare minimum shit that I do with it. And P and then I say at the end, okay, where do you think you are now with AI? And ones and twos, they're like, Oh my God, I'm not even close to where you are. I'm like, dude, if you're not even close to where I am, I'm worried for you right now. Cause this shit is so easy to figure out that you just got to be curious, right? Why do you think people are still not curious enough with all the hype around AI and what it can do? Why do you think there's still this trepidation of like, eh, especially like senior sales reps, you know what I mean?

Who are kind of like, ah, you know, my old school, I don't need that shit, you know, blah, blah. Why do you think that there's that hesitance to dive into this? Is it a fear? Is it a lack of knowledge? Like, what is it? I'd say it's twofold. And I actually did an event with Pavilion just on this, you know, where does everyone start with, with AI? I think there's two things. One, people feel like they're almost too far behind. I wouldn't know where to start because there is so much happening. And I don't think there's enough encouragement from businesses, from leadership to say starting now, you know, you're not too late. Like we're all too late, arguably. Um, I think that's part of it. But then the other side is leading by example.

I don't feel enough leaders. They're asking their team, do AI. And they're like, where do I start? And they're like, I don't know, just do it. And I think there's an element of that, just showing those quick wins, like putting an arm around the team and, and like, you know, getting kind of hands on with, just like you were, you know, demonstrating if I can use it and I can build this, let's get creative. What like team, what do you think we could, we could achieve here? Where are the bottlenecks? Where do you think that we could unlock value and, um, creating like a comfort there? I think so. Actually, the third thing is there is a fear, but it's not so much of like the unknown and where do I start?

It's, am I allowed to do this? Especially at bigger organizations. There's like fear for their job because of the risk of using it. And, you know, they're getting these emails being like, hold off, don't use X, don't use Y, we'll sort company licenses. And they're like, uh, what if I put some questionable information in and so forth? And they're not enabled in the way they should be, because you can use AI in a very safe way. You need an AI policy as a company, but slightly the boring side of it. Well, I mean, yes. And I don't know, maybe I'm just too, uh, flipping on this, but what's your perspective of IP at this point? Because my positioning is IP fuck like IP fuck off. Like there's nothing special at all about anybody anymore.

Everything is out there. If I want to learn about your business, especially if you're a publicly traded company, by the way, if you're a publicly traded company, 10 K's annual reports, all that shit, it's all out there. So I, I still kind of like scratch my head at internal, you know, security groups who are putting the restrictions on it. It's like, Oh, don't put any of our data in there. It's like, really? Like what special shit do you have that isn't like general knowledge at this point? Or at least I can come pretty close to guessing just by asking a general, like, so where are you with IP on that? Cause I, cause I'm like, fuck it, man. Just who cares? Just, just let's go. But obviously I'm, I'm, you know, a little further on the risk profile than, than security and compliance people and all that fun stuff.

So where's your head as it relates to IP? Yeah, I think understand the hesitation and the caution, but your team are doing anyway. So unless you put in the parameters, the guardrails and enable them to, to use AI safely, you're already at risk. So the longer you delay, the more frustrated your team are going to get and the more chance there's going to be, you know, some level of risk or, or an issue like that, then yeah, you're just going to kick yourself. And I think, you know, a good, a good example is like HubSpot. If you look at HubSpot leading by example, they've got their leaders sharing how they use AI in weekly all hands. They are completely, uh, going all in on AI from a product front.

Um, they've got leaders posting on LinkedIn about how they're using AI. Look at Darmesh, you know, co-founder CTO 20 years into this game and he's back in building hands-on with AI. Like that goes back to what I was saying. Like if you have leaders leading by example, using AI and saying, we can use it safely. We've rolled out Gemini. We've rolled out ChatGPT across the business. It's already there. Like these tools are enabled for large organizations. It's just, yeah. Um, the parameters, but IP, you know, if I look at tech, it's on our side, you know, we're building SAS. It's not what you can build anymore. It's when you can build it, how fast that, you know, there's no moat around product.

And I think that's the same with just with IP as well. Like it's, uh, you can hesitate and be cautious, but you're going to kick yourself and you'll end up being the next Kodak. Exactly. And that's where I think, you know, leads to, I think it's something that I know you believe in because of what you do is, is it, to me, it has nothing to do with what you sell. It has everything to do with how you sell. Right. And you know, so your product's great, whatever special sauce you think it has, if you're in that feature function in conversation, you've already lost because even if let's say your features and functions are the best today, tomorrow they won't be. And, and so you're going to keep chasing that.

Whereas how you engage with a client, the value that you bring to the conversation, you know, I've, I've won deals over my competition where they had the better product, like ultimately like the product of their service was technically better than ours. Um, but because of the experience they had through the sales process with me of just like helping understand and the value that I brought to each conversation and those types of things. Like I had a client tell me, John, the reason that we were going with you over, uh, the other competitors, even though we kind of thought that their training was a little bit, you know, better than is because every time we get off of a conversation with you, we learned something like literally every conversation.

We debrief after our quote unquote sales calls with you. And we're like, Holy shit. Like what he brought up, we got to look into that. We got to do some more research. And I give them some recommendations on this and go take a look at that and whatever. And they're like, dude, we want our sales reps to act the same way. We want them so that every conversation they bring value to the client and the client remembers it afterwards saying, wow. Right. And that mentality of like, somebody said this early in my career, which is, you know, they, they said that every conversation they have with somebody they want to ask at the end, like, would you have paid for this? And you know, not that you would have paid a million dollars or anything, but effectively, did you get enough value out of this conversation that you might've paid a few bucks for it?

And that mentality has always stuck with me. So let's talk about how reps sell with all the automation, with all the personalization, with your deal rooms and how you can bring all this and you can personalize everything to each buyer persona. Where does the sales rep fit into that equation? I think first and foremost, I'd recommend everyone to read how to win friends and influence people. I think, yeah, I know it's a classic and there's a million sales books out there, but the human psychology now of, you know, how do you be biocentric? How do you focus on, on what they care about and dig into their pains? I think it ultimately ties down to that psychology of they don't care about you and your product and your pitch.

You're, they need help. They've given up their time for you to listen to them. And I think it's got to start with that. Um, I think, you know, we mentioned earlier on this, on this podcast about research, AI makes that easier than ever arriving with a point of view and narrative, like a, uh, my understanding of your business. Am I right? Am I wrong? I think all of these show investment in, into the conversation, you know, like you did this start, this call you've researched me and I was like instantly kind of like builds trust. If it was connection, I was like, okay, cool. Yeah. This, yeah, this isn't just another podcast. Okay. I haven't had this before. And that's like, you know, it creates, uh, yeah, a level of comfort and it opens people up.

And I think, you know, in sales, our job is to build relationships, to build that trust, to get to that point of understanding how we can create value. So I think more so than ever, that that's a core component, but equally, if we put that piece aside, I'd say transparency, transparency builds trust and transparency in terms of process. I'm asking these questions because this is my job. And with that, I can go and, you know, engage our CS team. I can then speak to Susan's engineering and get that resource for that next call. So I think, you know, like putting the why behind why you ask things, why you do things, transparency in pricing, transparency in process, transparency in competitive, you know, like we love our competition.

We always put them on a pedestal. We'll always say like why people go with them. Um, and we'll never competitive bash, but what we will do is say, look, rather than us speak for you, uh, speak about, you know, uh, competition here, let's just introduce you to a customer and give their opinion on why they went with us, why they moved. And they won't say we're the best thing in the world. They'll give you the honest take of why they made that decision where maybe we could still, you know, improve. I think those kinds of things, like people feel less like they're being sold to. And ultimately they feel like they're kind of getting to know you, getting to understand your business and how you partner.

And I think that's the keyword partner rather than this is a tool where a vendor, like here's a piece of software. It's, we're going to be working together for the next 12, 24, whatever, 36 months. How are we going to get to that point where you feel like this is a successful investment and it comes from a partnership. Um, and ultimately the increasing rise or kind of awareness of sales and CS collaborating, because that's like the most common problem across every business. I think now more so than ever, that's going to become, um, such a powerful differentiator at the early, you can bring them in the more that they can kind of effectively collaborate with prospects to the point of them be becoming onboarding onboarded, sorry, is, uh, is key.

So a few pieces there, but for me, transparency is, is the ultimate one. Yeah. I think that's the, to your point, like the trust level of, of coming prepared for me. I mean, it, it, it sounds trivial, right? Because we should, I mean, for again, we've had the internet, the AI has just made it a lot faster for us to find this information, but the information has been out there. Like you could easily go to somebody's website, see what they do, see who they sell to all that stuff. It's always been there at least, you know, for the past 30 years or so. Um, but yet still reps show up and say, so tell me about your business. You know, what keeps you up at night? And like the stupid, generic, shitty questions that are just, in my opinion, like just a fucking waste of time.

Like I do this and I, and I've said this before on my podcast and I encourage every buyer to do this to every sales rep because they deserve it is, is you start the conversation before the sales rep gets going and say, Hey, right. You know, before we get going here, man, do me a favor. Uh, tell me, tell me what you know about me and the business so far, just so we can kind of level set here. I did that. I did this experiment about a year and a half ago. I had 20 sales reps sell me something in SAS too, by the way, this wasn't like obscure weird shit. And you know, I'm not like, I'm relatively well known in the SAS industry. And my website is pretty fucking obvious what I do 20 times, 14 out of 20.

Couldn't even tell me I did sales training. Like literally. And that's all I wanted them to do was say, well, Oh yeah, yeah. John, I know you do some sales training where some cool companies, you got some online and remote stuff and you know, on site. So yeah, I got a good set. That's all I needed. And then we could continue like 14 and I would just hang up on them immediately. I'd be like, all right, you wasted my time. I'm going to now take it back. See you later. Wouldn't even get them a second chance. And I, and I, and I worry right now that we've so over operationalized the sales process and we haven't taught on the, the, how to win friends and influence people, the, the ability to understand, you know, nuance of body language and looking somebody in the eye and using their name and making them feel comfortable that we're in this, we're in a really dangerous transition here for quite a few people, because I just don't know that they know how to sell or know how to, and when I say sell, not like the, what everybody thinks about selling, which is like convincing people.

Right. But it's again, more about helping people buy. And I don't know how we get back to that quite frankly. Yeah. I think the, like the project management aspect is more or more the responsibility of a rep than it used to be because the burden of buying is pretty heavy, the complexities, you know, the, uh, ROI calculations, the competitor analysis, the, uh, you know, understanding implementation, you know, what does that actually look like? Not just what tools they need to plug in, but the time investment from their team, all of those things, most buyers are not aware of. And then increasingly. So when you go up the scale and enterprise and so forth. So, you know, like we do this day in, day out.

And our job was to give that visibility of like, I'd spoken to similar companies before I'd been on this journey. And this is typically what can happen. Like, are you aware of that internally? You know, if I said that you needed to X, Y, and Z, would you know who to speak to internally? Cause I just want to prepare you for that. I'm not trying to create more work for you, but if you really believe that this is, you know, the right fit, then how are we going to get there? And I think, you know, that's why like mutual action plans or timelines and business cases, all of these are just, they're just tools to enable the buyer to be able to sell internally, to be able to project manage internally.

But our job as sellers is to do as much of the heavy lifting for them as possible, because they do not have time to put all of that together. As soon as they've got, you know, extra work, another priority pops up and they lose interest because as we all know, status quo is pretty okay. Unless it's on fire, man, I ain't dealing with it right now. You mentioned mutual action plans, which is a big part of Trumpet and what you bring to the table as far as walking through the process with somebody so that there's alignment. Why do you think mutual action plans haven't taken on more, taken on, been taken on more broadly in the, in the, I mean, we, I hear a lot of them. I see very few of them executed, uh, at least correctly.

Uh, there, there might've, you know, at a lot of times they're introduced late in the process, right. When it's, it's almost too late to, to have all that, you know, it's almost like, Hey, you did a POC. So I gave you a POC and then they asked for an extension on the proof of concept. And then it's like, Oh, okay, we need to put together a mutual action plan now because you know, stop wasting my time effectively. And they use it more as a, as a stick than a carrot. Right. So why do you think mutual action plans haven't taken hold more and why, why aren't we using them as much as we should? I mean, easy answer that they've always lived in spreadsheets and not Trump if, but you know, that kind of quick piece aside, I think, um, they've just never been buyer centric.

So there's no incentive for a buyer to come in, to collaborate, to use it. They're built with the sales process in mind. How do we get you to the point of signing? Not thinking about go live, you know, kind of the timeframe of seeing results. They're manual. They take time. Anything that is manual for a rep is like, if I work enterprise deals, sure. I've got time to do that. I'm working mid market. I'm working 30 deals at, you know, one time my, uh, my pipeline, they're not going to get around to like creating that kind of bespoke visibility, but ultimately again, I think it ties back to now should be the time to be thinking about that more so because buyers arrive knowing who you are, who your competitors are, what you do.

They're not there to be educated on that. They're there to understand like how days they move forward. So, you know, creating accountability, creating visibility helps to qualify. It helps to progress. It helps create momentum. And I think all of these things like reps just need to be coached on and they need to be made aware of, but what we see buyers are very receptive to it. You know, there is a lack of visibility in 90% of deals. The only visibility they have is there is a call in two weeks where they're going to get feature dumped, but they don't know really what they have to do to on their side to like, you know, keep things going. So the concept has always made sense. It's always driven value for, for, for, uh, reps that, that use them as intended and make them biocentric.

But something's been missed in, in terms of just educating reps on why use them and, um, and how to make them biocentric ultimately. Yeah. I was going to say how to make them about the client as opposed to about us, which leads to personalization, right? Um, obviously personalization is the key to reduce friction and a lot of stuff and tailoring everything where, where, where do you see people miss, um, or, or mistakes that companies make when it comes to personalization, right? Is there, is there a kind of a balance here? Like there's certain things you should absolutely personalize. And then there's certain things you're personalizing for personalization sake. And it really, it actually detracts from what you're doing here.

Where are the biggest mistakes you see when making personalization? You wouldn't, we're trying to personalize things. Like instant thought outreach. Yeah. You went to this university, you support this football team, whatever it might be. Like, yeah, that's the default. Just yeah. Generic, like people are too busy to care about the kind of fun stuff, but I think in the sales, you know, through the sales process, I think you can like over personalize in a lot of ways, or like think certain things are personalized when it's like a surface level personalization that I always say, you know, fake personalization is worse than no personalization at all. So, so I'd rather you be relevant to me than personalized.

So where like outside of product, cause I agree with you. I think that you, and that's where AI I think is failing horribly, just like reps are like it just fake personalization, bullshit doesn't matter. But like through the process, like, okay, yeah, I got to personalize for this. And do they spend too much time? Do they, do they over like, where is that gap? I think it comes down to. Well, the one, the key one that we've seen is as a trend across businesses that we speak to is a lack of personalization in terms of messaging that's being shared from your champion then internally. It's very like one size fits all. This is what we do for Acme. Give that to the champion. They share it. And then finance reader and they're like, no, I don't care because that person's from marketing and is very marketing related.

And, you know, uh, and then someone from IT looks at it and they're like, I don't see any mention of integrations, for example. So that's, you know, just instantly ignore. Um, and I think that goes back to our job as sellers is to ask our champion, who do you think is going to be involved? But rather than just say that, who do I think is going to be involved? It's who do I think, who do you think is going to be involved? I have a feeling it might be Sarah, Lucy and Michael, because usually they're the type of roles and people from departments that we speak to. And I can imagine they're going to want to see X, Y, Z. That is personalization. It's doing the thinking on behalf of our prospect and equipping them with content tailored to those like persona level content.

That's, you know, enablement teams that are brilliant at this, like really helping our reps understand the importance of personas. So I think that's one piece. And then I think the other is talking their language, you know, talking about their products, talking about their customers, you know, uh, maybe it's a football team like, Hey, I see that you've got Manchester United on your website. I'm sure you would love to sign Liverpool as a client. Oh yeah. Actually, we've got to deal with them at the moment. How did you know? Like again, it just, it's all about kind of being in their world and thinking about their own customers. Cause that's who they're building for. That's who that, you know, they're solving these pains for.

So if you think about it, less of me to you, more about me to you, to them, that's how you kind of get there. So personalization is an interesting one. And equally, I still don't believe most organizations help reps break it down. Cause when they say personalization, too many reps think, yeah, personalizing my emails. It's like, no, no, no, no, no, no. The buyer journey is so much more deep than that. Yeah. When they come in and out, like how do you, cause inevitably the client's going to pause and come in and out whenever they feel like it, right? There's not, we can't force them, you know, through our process. So I guess, how do you meet the moment in value? Like, or how do you teach a rep to meet the moment in value?

When I talked to you two or three months ago, um, you know, we had these good conversations I understood and now you're reaching back out to me and it's like, Hey, we're ready to go or, or, Hey, I just got one last question and a rep just kind of, ah, right. Gives whatever the information is and loses control a little bit. So how do you, how do you coach on meeting the moment of value now that clients are coming in and out whenever the fuck they want? It's a, it's a difficult one. Cause there's that muscle memory. You just want to like knee jerk reaction. Yep. We can do this. Let's go. Uh, the thing that we, we encourage the team is anytime you, you get information from a prospect, from a, from a customer, just ask why ask that.

Why just ask that like X, just dig a little bit deeper, no matter what, no matter what stage in the evaluation, because discovery never stops. Even on that final call with the CFO, where you're talking through the final bullet points, negotiating, whatever it might be, never, ever get complacent, never, ever signed until it's signed. Uh, and I think that mindset of, um, continuing to like scrutinize and almost challenge yourself that this deal isn't going to happen. And, you know, uh, really thinking that discovery is a continued journey, even post sale as well. That's work for our reps, right? I should be interested to hear your thoughts there. Like what would you, uh, you answer to your own question?

Well, I think it's, it's about the documentation of the process up until that point. Right. So I, you know, I'm a huge fan and I know this is kind of aligned with a mutual action. I, my mini mutual action plan that I don't use kind of formal mutual action plans. My sale isn't, you know, that complicated, but, um, I have these mini summary emails, right? Where after every conversation, I summarize the conversation key takeaways, and then I send it to you and I ask, Hey, could you do me a favor? Let me know if this is all accurate and if I missed anything. Right. And it's the timeline, the process, the, the, the problem, the impact of that problem, the people who are involved in the next steps, right?

Like kind of the core stuff that, that are, are we still on the same page here? Right. Um, and so I have that usually readily available. If I get the call, if I get the email to have the conversation and the first thing that I tend to do is I might use, you know, it depends on usually I, I can schedule the call. Right. So as opposed to like, just catching me, it's, it's rare these days I get a phone call from somebody and I'm, and they're like, yeah, we're ready to go. It's like, Hey, John, can we set up some time to talk about this? So if that's the case, then I just put together a simple shared, little shared agenda, looking forward to the call. Um, just want to make sure that we stay on top of things.

Here's a few things I want to make sure a confirm everything still on, on pace since our last conversation be. And I I'm with you as far as always discovering, um, my, my favorite question to ask people, second, third, fourth, fifth meeting doesn't matter. And it doesn't matter even if it's only been two days is what's changed. Right. So if, if, if I was selling to you and we had talked last Friday and this was the next call, you know, before we even got started, even with the agenda, it's a, Hey Rory, before we get going here, you know, uh, what's changed since I, you know, not has anything, not a yes, no question, but Hey, so what's changed since our last conversation because things are moving so fast right now that it's a nice way to get somebody talking first of all.

And, and sometimes they don't think anything has changed, but they'll be, Oh, well, you know, we hired a new, or we put a new job posting up for this. And it's like, Whoa. And you're either looking at that as a sales are being like, ding, ding, ding. That's great for us. Or Holy shit. That's a red flag. Right. And you know, if nothing's changed, well, great, you know, so appreciate you reaching out, uh, before we get going again, could, is it, is this all still accurate? Is this your timeline, your priorities? Is this still the problem that we're trying to solve here or what's changed from that? Right. Uh, nothing. All right, cool. Now let's talk about next steps. Right. So now I know how to bring value to the equation.

So it's more about the documentation of the process that, uh, that I lean on. That's a very, uh, relevant question in this current climate. Oh yeah. What's changed? No, a hundred percent. And, but that's why if you smelled S and B, like, Oh my God, everything changes, everything changes daily. And that's why priorities are such an important thing for me. Right. Cause when you and I talk about what are your priorities, I always tell the reps, like in order to, to, to uncover, you can't create urgency, right. But you can uncover it and you can drive it. But the only way to really do that is to align with the priorities of the executive. Like when the executive stands up and says, this is what we got to do to be successful this year, you know, these three things or whatever it is, or whenever they said that last, if I can't tie my solution to one or two of those, good luck selling anything of significance.

So I'm constantly like, okay, I understand what your priorities are as a, you know, as a business unit, you know, you gotta, you know, increase sales, you gotta get a bit more pipeline. That's fantastic. Great. Good. How does this align with what your CEO said and what you guys are trying to accomplish this year? And does it still align with those priorities? And if it does, I'm going to push really, really hard to get this deal because it's in your best interest. But if it doesn't, I got to reshape that, understand what those priorities are, see if my solution can still align with it. And if not, I got to find a different angle. Yeah. I love that. The, uh, helping your champion think about how to sell this in termy, those like preempting those questions that are going to get asked and whose desk it's going to land on.

Yeah. Well, it's, it's actually funny too. Like the, again, going back to the, the, how archaic I think so many of us are in sales, especially outside of SAS, like you step one foot outside of SAS, man. It's like sales, 1985, all over again. Like I did a simple one with the other day with like a company who sells to lumber yards and these types of things. And just afterwards, instead of sending them the proposal, I just did a video for them. I was like, Hey, you know what? I wanted to kind of show you what the training is and how like this does based on what you told me, like, here's what you said your priorities were. And here's how my salute kind of aligns with that. Just instead of just sending over a document with a ton of words on it, I figured I'd just show it to you a bit.

And like their feedback was like, Oh my God, this is incredible. Like if you could show our team how to do that, I'm like, all I did was I was actually kind of lazy because I didn't want to write it. I didn't want to type it. So I just lit up a video and be like, yeah, let me walk you through this. And they fucking thought it was the best thing since sliced bread. And I was like, Oh, okay. Yeah. All right. We got, we got some work to do here. Yeah. That's the thing. I think we're overwhelmed with tools these days. Like, what was it? 2015, there's 3000 MarTech tools. Now there's like 35,000. Like where do you start? But actually, yes, it's overwhelming, but equally we're inundated with the ability to create ease, to remove friction, to share quick videos, snippets, and to personalize without it being heavy, because it used to be super heavy.

So yeah, it's, it's, uh, it's kind of like easier than ever, but also harder. It's easier than ever. If you care, it's easier than ever. If you give a shit and are curious enough to, to figure this stuff out, it is not. And this goes to my thing about sales into every profession, quite frankly, the ones who give a shit enough to figure this stuff out, leverage this stuff as it's a superpower. The ones who are using it as an answer engine, where they're just looking for the answer, copying, pasting, and whatever, or avoiding it altogether. Unfortunately, they're irrelevant. And I think that's unfortunately a large portion of our population. So. Yeah. It is frustrating when you've got this, uh, breadth of amazing tools, data, everything, and you're not using it to your strength.

You're using it to become lazier or just to make the copy paste sales process that you're, you know, uh, you're stuck in even more copy paste. It's, uh, frustrating to see. It is, but it also is a chance for differentiation going back to the original, like what you sell versus how you sell. Right. And I think that's what you guys are looking to do. You're doing a great job with and helping clients and, and the right type of sales reps figure this shit out. So with that, right, let's, let's wrap it up here. Talk to people about where they can find more information about you, about what you're working on and, uh, Trumpet and everything else. Yeah. Uh, we're all very active as a company, as a team on, on LinkedIn.

We live and breathe it, uh, equally just head to send trumpet.com and try out for free. You can check out, uh, bring case studies of all our amazing customers, but equally, I, I love to have conversations about sales excellence, go to market, anything. So yeah, hit me up on LinkedIn. Always happy to reply. Awesome. Right. Well, I appreciate you coming on the show, man. I enjoyed the conversation. I appreciate it. Thanks for having me. Absolutely. And everybody hopefully enjoyed the conversation as much as I did. And like I always say at the end of all these podcasts, go out there and make somebody smile today. Cause no matter how bad your day is going or how bad you think it went, if you make somebody smile, you know, you had a good day and the world needs a lot more of that right now.

So thank you all very much. And I will see you on the other side. Hey everyone. I hope you enjoyed that conversation as much as I did with your support and our incredible guests. We're one of the top sales podcasts out there right now. And I can't thank you enough now to keep the momentum going. It would mean the world to me. If you could go and leave a five-star review on your favorite podcast platform and share some of your favorite episodes with your network. Also, I am super excited to be launching my new newsletter where I'll be sharing everything I know and everything I'm learning along the way while I'm out there selling every day, just like you go to jbarrows.com slash newsletter to sign up today.

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