Jarron Vosburg: Why Everything Should be an Experiment

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. Today's episode is with Jaron Vosberg. He's the VP of Sales at Jump Crew, which is an outsourced sales and marketing partner that helps you drive and convert more leads into customers. Now, Jaron wrote a post a little while ago that really caught my attention. It said, salespeople, humor me with a hypothetical scenario. You need to connect with decision makers, but aren't allowed to send emails or make phone calls. He then went on to outline different unique approaches and the testing he did to figure out which ones worked and which ones didn't.

We talked about the give a shit factor, also why it's so important to treat everything like an experiment these days, how to structure experimentation with the outcome in mind, celebrating failure, and how to coach towards agility. This episode is filled with tactical things that you can use today to help break through the noise. Let's make it happen. What's happening, make it happen, family? Big shout out to our partners today, Gong, Vidyard, and Chili Piper. Gong's data is more than valuable. It's cornerstone in any organization looking to collect the data that's going to tell them where they can improve and where they need to spend their time making changes. Vidyard makes it easy for people to use videos anywhere.

No matter whether you're sending videos in email or on social media, posting them somewhere, or sending them in a DM, Vidyard has got you covered. Our friends at Chili Piper are so much fun to be around. They make it easy for people to get on your calendar. And every sales rep has got to have this function locked in. It's one of the most important things we can do as a seller. How can I get you on my calendar easily? Chili Piper can make that happen for you. Be sure that you're checking out all these great tools. And now, let's pass it over to John to find out who's joining him today. See you soon, everybody. John, what's going on, my friend? How you been? Hey, I've been doing great, brother.

How are you? I'm doing all right, man. Thanks for joining me here. And I remember a while back, you'd ping me on LinkedIn saying, hey, man, if you're ever looking for some guests, come on the podcast. At the time, I was cranking. And I was like, yeah, yeah, talk to my team. And then I started getting some recommendations. I'm like, I don't know if I love some of these recommendations. So let me go poke around at people who actually know what they're talking about and can have a good conversation and came back to you. So I appreciate you jumping on here. Well, I'm glad you worded it like that. I won't take it as just being the only guy available for this time slot. No, absolutely not, man. I get hit up all the time.

So, John, just so the audience gets a little bit of perspective here, give a little bit of background, where you're coming from, a little bit about Jump Crew, and then we can dive into what I think is going to be a pretty interesting conversation for people here. Yeah, absolutely. So I'm currently the vice president of enterprise partnerships at Jump Crew. I've been here for the last six years. Jump Crew is responsible for building qualified opportunity pipeline and closing deals for companies that are ready to scale. And so we work all across the board from companies just going to market for the first time, companies that have been around for a little bit and have a problem or see an opportunity to big fortune 1000 companies that are looking to pour gasoline on the fire to see a team who can turnkey, get it rocking and rolling.

I came to Jump Crew after having never been at a job for more than two years. Like, I'm a shiny object syndrome kind of guy. And like, I wanted to be a film director. And I studied film production in college and worked in that world. I wanted to be a talent agent because I wanted to be Ari Gold from Entourage. And my soul was sucked out of me for two years. I learned a lot, but didn't love Pat. And then I pendulum swinged all the way over the other way. And I quit that job with no money in the bank and tried to build my own company that blended the things I was into at the time, which was electronic music and fitness and not being in front of a computer. So I built a audio guided workout app that we bootstrapped, took to market and had some success and ended up sunsetting for a number of reasons.

And then I had to go back to kind of corporate life because I had met my now wife and wanted to show her like, hey, I can actually make a little bit of money here. And I'm not just some degenerate. And I ended up working at a company based in Colorado that had built a software for funeral homes and their staff to place obituaries and newspapers. And they were shortly acquired by Ancestry after about six months. So I was a part of Ancestry.com. So you're seeing a theme here, right? Like all over the board. I'm like, what the heck am I supposed to actually be doing? And so when my wife and I moved to Nashville in 2017, I said, look, I feel like what I'm really looking for is somewhere where I can get the output that matches the input.

And in my mind, I was like, that seems like sales makes sense, right? Like you kind of eat what you kill. Like when we find somewhere where I can just outwork it. And that's how I landed at Junk Crew. I think we were maybe 40 people at the time. We're almost 300 people now. Started as an individual contributor and had the opportunity to move up to team lead, manager, ended up being the manager and director of some of our biggest client accounts for a while and have been in the VP role since June of 2020, mostly responsible for new business. Love it, man. Yeah, that does seem a little bit all over the place. I mean, I didn't take the same track, but I was kind of the same walking into college.

Like my first major was art. My second major was engineering because that was what my dad did. My third major was biology because I don't know why not. I think I went through every major and then I was like, I'm just going to land on business here. So this one's the easiest one for me to graduate with. Yeah, it's like I can actually find a pair of matching socks at 18 years old, let alone like determine the future of my entire professional life. I still find that insulting. I really do. I can't believe that we still ask kids at 18 years old that they have to define what they want to be for the rest of their life when you don't even know who you are at 18 years old. It's bananas to me. I don't get it.

No. I don't get it. But let's jump into this, John, because you had posted something a while ago about, you know, that caught my attention and it was about how, pretend you don't have phone, pretend you don't have email, how would you do outreach? And we were talking pre, you know, before we jumped on here about how your TAM is so wide that it's not exactly obvious what the best approach is. And then you went through a whole bunch of different experiments to figure it out. So could you kind of just reframe what you had said to me beforehand about why? And then let's get down into, you know, what it takes today to break through that noise, because I think so many reps right now are acting like robots and they're getting replaced by robots and it's going to happen now faster than I've ever seen.

And so creative ways of engaging and developing relationships is paramount, in my opinion. But I'm worried because of where we are right now in the terms, in the sense that it's a remote working force. People are coming in without having to sit in the bullpen and learn from other people. There's no real empathy anymore for anybody. You swipe left if you don't like somebody, you know, all that shit. So could you kind of just, let's start with what you talked about with Jump Cruise TAM and what forced you to change things. Yeah, absolutely. And I want to preface this by saying that I deeply, deeply believe in Outbound as a strategy. I think that it can still fundamentally dictate meaningful pipeline for the types of customers that you want.

The challenge is that unless you are approaching it in a way that is at the very least different, if not at the best, thoughtful and intentional, then you're going to really struggle to drive meaningful results. And so the example of Jump Crew in particular is, you know, our model is that there are so many use cases for where a team like Jump Crew, who builds fully dedicated sales departments on behalf of our clients, can be deployed. Companies who just raised a seed round and don't have the time, interest, or expertise to do it on their own, all the way up to the, you know, Fortune 1000s and everywhere in between. The challenge is that because of that, building a systematic outbound program that can yield real results has to be different.

It can't be spray and pray because the TAM is so large. And so we've gone through a couple of different iterations of outbound. And interestingly enough, had various levels of success in every single one of those. But it's always a vault. It's always a vault. So our very first pass at outbound was built by geographic territory, where we said I had, I think, six reps at the time. Let's break the country up by some of the largest cities, largest markets. And then what are the other indicators that we know are typically a good sign of a customer for Jump Crew? So we were looking at companies that were hiring for AEs or SDRs or sales managers even, as a good temperature check that this could be a fit.

And that's an easy talk track, right? It's like, I saw this. There's a different way. Would you be open to hearing about it? And that really works. That really worked well. Because that, for us, is one of the only indicators we have at face value, that there's a need. The other strategy we took simultaneously was look at current customer base. This is not going to be revolutionary to anybody. Look at current customer base, build use cases around that, and then build an account profile for target lists based on that. We've had success here. Here's what we did. I think we can replicate those results. And that has also had a lot of success historically as well. So flash forward, we're finding some results here.

That's working pretty well. COVID happens. And what we saw, especially as far as people start really coming back from COVID, is that our fortress around our inboxes has been more fortified than it ever has. It's like you just, nobody cares, right? Like if you're coming in and your email starts with, I hope this finds you well, you immediately hit, like you don't even have to read the rest of the email. And we certainly experienced something similar no matter how custom or thoughtful the email was. So we started to start thinking about that subject line, but not subject line, but the line that you see in your email. The first couple of words you see, that is your real estate. So you've got that to work with.

So then how can we leverage that real estate? So our first pass at that was pulling something very specific to the prospect. So if I said something like, hey, John, I saw your post about something, right? That's going to get a note because it is personal to that person. It shows I did the work, right? And what this would say laying the foundation for what we're eventually kind of moving into these days is pre-work. This idea of actually doing some work in advance to show why this connection makes any sense. Now it really started to work. We closed deals leading with that strategy. I read this. It spoke to me. Here's my interpretation of it. Hey, as a side note, I think there could be a good fit here.

Okay. Can I pause there for a second? Because this is the line. What you explained there to me is the line between fake personalization and real personalization. Fake personalization, and I'm sure you get them just as much as I do, is, hey, John, personalized thing. I see you went to University of Maryland, right? And then it hard cuts to some piece of shit value proposition that I would have no fucking interest. I actually give you less points these days for doing lazy-ass personalization without making it relevant. So how did you talk to your team about finding that thing, and then to your point, using kind of a business case approach to it to say, hey, I saw that, and there's actually a reason I'm reaching out because of that, not just because that's the personalized piece I need to plug into my stupid template here to make sure that it shows on the first 10 lines.

That's right. Like, I like to think about it this way. If what you're using as personalization can be a variable field in your CRM, it doesn't count. It doesn't count. So if it's like a crunch base, funding round, or a university, or the location, or whatever. And so actually, I was just looking, because I pulled up this example of one that actually turned into a deal. And the beginning of the email says, I stumbled on your something blog, and I've binged the wealth of insight. One of my favorite takeaways was the questions that you ask candidates in an interview. I'll definitely be adding the, what's the last book that you read to my list of interview questions. And I told him what my favorite book was.

I was like, speaking of interviewing candidates, and I switched the tone to like, look, finding talent is tough. Like, and then you've got to build a team, you've got to train the team, you've got to manage the team. And that's a pain point that I know a lot of folks are having to struggle with, especially now. And that was the pivot that I used to then show the value prop of Junk Crew. And then, of course, the soft call to action at the end was, hey, if that resonates, let me know if there'd be any value. Not do you have 15 minutes. And I've seen that, remember, just keep getting shorter and shorter. People are like, do you have seven minutes? Dude, I know, exactly. That's amazing that they think that that's going to have any impact.

It doesn't. Another hugely successful piece of this email structure has been the often forgotten PS. I love the PS as a tool because sometimes it draws the reader's eye all the way down to the bottom, right out of the gate. So that PS, and I always make the PS something else personalized. He said, this prospect said in that post that if someone doesn't do homework on me as a prospect, I'm not going to do anything. So I said, I hope this email fulfills your advice about doing a little homework. I'm trying to connect with you. I'll drop to you a connection on LinkedIn. So like just bookending that whole thing and making it co-keys, right? And that prospect signed the deal about 60, 90 days. So again, more validation that connecting the dots with personalization matters.

Now that was 2019 when that deal happened. So a lot has changed, right? A lot has changed. I'll tell you the story about what really catapulted this concept for me is because I was a buyer. Um, and I was doing some research on a, on a buyer intent and I was doing some, some, some look around. So I wanted more visibility to like, I wanted more visibility to like who was on our website. And then I thought we could use that insight to then provide the sales team with some outbound guidance, right? Something to equip them. And so a couple of days later, I get a slack from a salesperson at Junk Crew. He was like, Hey, I've got a buddy who works at this company. Uh, he said somebody at Junk Crew was doing some digging.

He wasn't sure who it was, but he thought it might be you. And I was like, Oh wow, that's kind of cool. Like that's a good use case, the tool. So he emails me directly. I'm like giving my email. And not only does he just email me directly, but he emails me like a whole breakdown. Here's what I'm seeing. Here's how I think it would work. And this dude like did the work in advance. He gave me the plate and I said, Hey, now like there's something there. And we signed up with that. We signed with that vendor. Um, and so it's got me thinking a lot about like, what's the next space. And I've got one other thing that I'm probably going to tie this all together. Um, there is, um, there's an Instagram accounts for dumb dudes like me called, I think Friday beers.

And, um, they take like these clips from movies and then they'll put different text over the clip of the movie. So it has a slightly different meaning. And I was like, that's an interesting intersection of, of this type of content. It's visually engaging. It's unique. People can relate to it. And so the idea for us was what's the next level of us innovating creatively in terms of outbound. If we weren't going to use email, we weren't going to use phone calls, what would we do? And so I pose that to the team as just a thought exercise. And the responses were interesting because it was mostly just blank stares. Like, I don't know. I don't know. And there was that saying that, you know, a poor craftsman blames his tools.

Like if you've got a hammer or something into the wall, but you don't have a hammer and a nail, how are you going to do it? You have to figure out how to do it. Yeah. And that thought process is a muscle that is just not flexed very often these days. Yeah. And that's where I saw a huge opportunity. And that's where the idea of creating these videos came from. And so the thought was, instead of me sending an email into somebody's inbox where I have a percentage of a percentage chance of having a really meaningful impact, if it isn't done right, what can we do that's different? And then also the idea was, how can I get this to scale further on a one-to-one? A one-to-one because I want scalability and another byproduct of that that we realized was that if we started to leverage video that we posted through social, not only is the potential prospect and the prospect account seen, but other people not at that company are seeing and seeing our thought process and seeing our methodology.

So the idea became, let's build a target account list for each of these accounts. Let's actually film a video audit of what we're seeing on their website that we like in terms of customer acquisition. Let's see, are they hiring for salespeople? What's the description of those salespeople? And then let's actually build a plan in real time for them. The research to prep for those videos takes maybe 30 to 45 minutes. The shooting of it takes maybe 10 to 15 minutes. And then once it's posted, it lives in perpetuity. And so we would take these accounts, we would write up a write-up that was like, have you heard about this company? They just released this report. We did a breakdown on the report. I did one for Drizzly, who released an annual report.

I broke down every different piece of their annual consumer report. And I said, if I was going to build the ad sales team for Drizzly's new retail ad network, here's how I would do it. And then I put that video online on LinkedIn. I tagged Drizzly, and then I direct messaged it to who I thought was probably the decision maker, which was their SVP at the time. And then I emailed. And what was amazing to see from the results, and actually I was looking at my recap doc here, is that that created a connection on LinkedIn. The visibility of that post was in the tens of thousands. And I got a response from that SVP, and we were able to actually communicate over email. That was the thing we did. So let me ask, so did you literally, like, that was your pitch to them, right?

So it was specific about Drizzly. It was about their website. It was what you could do for them. And you put that on LinkedIn, like a public to everybody, and basically saying, hey, everybody, I'm prospecting over to Drizzly. This is how we're doing it. And, okay. Everything you said is correct, except for one slight distinction, is that in my video, I wasn't like, I'm trying to sell to Drizzly. I said, I don't know if you saw it, but Drizzly released their annual consumer report. And there's some interesting insights. I was like, tequila's on the rise. Ready to drink is on the rise. Millennials are drinking red wine. Okay. Now, how is this valuable to brands in those three categories? Here's how.

Now, how can those brands leverage the Drizzly retail ads network to promote their products at the point of purchase? And so then we connected the dots there. And so it was a standalone piece that showed value around our philosophy, but then obviously it was a ploy for us to prospect in the Drizzly. Love that. I love that. Because that's what I was like. I'm like, wait a minute. Because I've seen people before be like, I'm trying to get into X account here, and this is my approach. And it's like, somebody help me. It's like, all right, come on. You're crowdsourcing prospecting here. I appreciate it, but don't be too lazy. But I think what you outlined there is multiple levels of value, right?

And I think that's where we're getting to. I actually think that with the tools like ChatGPT and everything coming out right now, I genuinely think that this is the year that the no value interaction of a sales rep goes away. Like the tolerance for the no value interaction, because I'm going to start getting so much more value out of, you know, a robot, basically. I mean, I've been thinking about this a lot. Like if you think about, what do you think about spam for a second, right? Like why do we hate spam in our inbox? Why is it, why don't we hate it for the most part? Because, what do you think? Like what do you, there you go. And it's not relevant to me. Most of it is not relevant to me in any way, shape, or form.

It's just data dump of here's how great we are. Let's talk, right? And I mean, you might, you know, every once in a while hit a rock solid, like, holy shit, actually, I didn't, but few and far between. Now, fast forward with all the artificial intelligence, with the ability to scrape the internet and know everything about me. I look at Instagram, for instance, and I look at Instagram and I'm like, I've gotten into the point where I have, like, I don't like that ad because it's irrelevant. So now that I've been using Instagram for enough. Now I scroll through Instagram, I'm like, oh shit, like that looks pretty cool. Like, that's kind of interesting. Like, I want one of those. I didn't even know that was a thing, right?

So I actually don't mind the majority of the ads anymore on Instagram because they're kind of things that I find cool. Well, if we fast forward, there's no way to me that that doesn't happen to our inboxes. I think that technology is going to be so good that they'll be able to scrape the internet, everything John said, most relevant up-to-date thing, what's happening in his marketplace, and then serve me shit up in my inbox that's just like, whoa. Like, yeah, that's a great idea right there. And guess what? I don't care whether it comes from a robot or a rep. That one. I don't care. I want to talk to somebody eventually, but the thing that shows up in my inbox, I don't really care. As long as it's relevant to me, as long as it's got something to, you know, gets me to think about something.

And so that's where my, you know, what I'm trying to wake reps up to is that reality. Like, that's not, I don't think that's my opinion because you've seen it happen in the social channels and we're just going to take that and move this over to this now that we have these type of tools. I mean, Microsoft just invested 10 billion into open AI. They own LinkedIn. Like, you don't think that Microsoft's going to be able to push a button and all of a sudden flood your inbox with shit that's like actually relevant to you. So I'm curious from your perspective, how do we, what you're doing is something different than what I notice out there. Most of us, including our education system, by the way, is like teaching reps to be robots, right?

And we're not giving them the creative liberty to try different approaches out or whatever it is. We invest in tools like outreach or whatever. Marketing comes up with the content because they don't want reps to screw it up. They force it in there and the reps press play. And with that, those reps are acting like robots. So they're going to get replaced right robots. But the problem is, is that they're not developing any business acumen. They're not developing any empathy. They're not developing any creative skills to figure things out. So, so how are, so what have you seen with your team with this kind of approach of yours where it's like, Hey, let's try this. Let's get creative here. How are you helping them evolve versus just execute?

Because I think execution, I could tweak a computer to do execution these days. I need people who have empathy, curiosity, and business acumen to eventually be able to have a conversation with somebody. So what are you doing at your organization to develop that type of talent? Because I think the development of talent right now is shifting drastically and it should. Yeah. Okay. So as a couple of things, one, I think it's a philosophical approach to the profile of the sellers that you bring into the organization. Jump Crew has very intentionally distanced ourselves in every way, shape, and form for what is traditionally known as the outsourced SDR model, right? Because for better or for worse, that has a negative connotation to it.

You immediately think offshore, you immediately think call set, you immediately think telemark. And interestingly enough, a lot of the companies that I would say consider themselves in that category still leverage near shore or offshore resources to keep costs low. And that's okay. That's, I mean, that, that, that model could work and that, that's fine. Since day one, Jump Crew's reps have been local. Jump Crew's reps have been fairly compensated by fair work and value and uncapped commissions. Jump Crew reps have had expectations as to what they're actually going to be selling because when they come into Jump Crew, they could be selling anything. They don't know what account it's going to be, you know, until they're in the interview process and we're connecting the dots with their experience and their temperament and the client and making sure that there's a good match there.

And then when they're in the organization, there are some things that are always going to be static. And then those things that are static are, you know, why is the product that we're selling valuable to the end user? And how does this client want that product to be represented in terms of their brand aesthetic, the messaging, like that all has to be consistent, right? So that has to be continuity. We have to set the expectation with our clients that like, this has to be a laboratory. If you remember the scientific method from your sixth grade science presentation, like it was hypothesis, test, conclusion, right? Something to that effect. And so reps have to know, here are the guardrails. Guardrails are, this has to be the same.

Everything else is up to you as the individual to bring ideas to the table on how best we can go about doing this. Give me an example. Jump Crew had a client where we were selling social media management, right? So this client could take on building content and actually managing the reporting, all those things. And we had a seller who was running with the top track that we had developed in the first phase of this, running with it. And, you know, the lead in would be, you know, hey, is there somebody who manages social media or, you know, we're a company that helps with this side of the earth. One day, this rep got off the phone and said, hey, I'm going to try something a little bit different.

Here's what I'm going to try. And the rep said, I'm going to try just picking a specific piece of content on that person's current Facebook page and seeing if I can figure out who was responsible for making that piece of content because I like it. So the next call he made, he said, hey, I have a kind of a strange question. I found this post that says this side of the other thing. It really resonated with me. Do you know who made this? Was this you? Was this somebody else on your team? And they're like, oh, well, that was John that made that. I was like, oh my gosh. Well, first of all, you guys have a gem in John. Second of all, is he available by any chance? Like this is a huge shot in the dark, but like his word resonated with me.

I had kind of a weird idea. I wanted to run by him. And so if he's leading with this really soft and very complimentary approach first, just to show I'm a human being, something specific about you spoke to me. And I just want to have a quick conversation. You know, he didn't know sales, but he hasn't mentioned what company he's calling from. He hasn't mentioned why he's calling. And we actually played around with how long can you go in that call before you say where you're calling? And it kind of became a game. And then when he got that person on the phone, then he's just talking about how great their work is. I remember we had a client, we saw an ad in a magazine, and we thought that the ad was awesome.

It was genuinely really good. And we called and figured out who created that concept. And then we were in their office like a couple of weeks later and sold that deal. And so taking that slightly different approach is the margin where you can empower sellers to be themselves and to come up with new ideas. And so every week when we're reporting back to clients and we say, here's what we tried, here's how it went, good, bad, or otherwise, here's how we suggest we pivot. That you can't replicate with AI. That's human. That's not artificial until. And that, and therein, I think, becomes the problem in the sense that that's not necessarily scalable. That's right. Because I call that the give a shit factor, right?

It's like, and this is the exact, and people who've heard me on this podcast have heard me say this before, you know, when Morgan came on board with me, he was doing great and we were creating cadences and he was going through and we got good results, but then they plateaued. And he was like, dude, I don't know what's going on. Like, I don't know why I'm not, you know, I'm not getting results. I feel like I should be getting better results based on what we're doing here. I go, Morgan, nothing's going to change. And so one thing does, and it's when you start giving a shit. And he's like, what? I go, look, I know you care about working here. I know you care about your job. But until you start genuinely giving a shit about the person on the other end of that email, the other end of that phone call and thinking as a person, like your results aren't going to change.

And that's what I tell my team. We have our, you know, now, you know, I got four other trainers and we all have our target lists, right? Top 25, whatever that is. And I told them, I go, I don't want you to just pick those top 25 based on basic demographic information, right? Just because they have sales reps and they're in these industries and whatever, that'll get you close. Okay. But then I want you to go through each one of them and find a connection. And I don't mean to send an email here, like you'll send that later, but I want you to find a connection of why you personally want to work with that company. Because if you can find that connection, then it's real, then it's genuine. To your point, a robot can't replicate that because that's me.

Like me personally, I want to work with you, John, right? So it's this growth at all costs that this SaaS industry has been in line for the past 10 years, right? And it's, it's over automation. It's over templatized. It's over trying to fit everybody into a very specific box of very specific segments and all that stuff. And, and yeah, I think it scales to a certain degree. But now I feel like we're going to come to a reckoning here where you're not going to be able to grow like that as far as mass, you know, customization or mass automation. And so I'm just kind of curious. I kind of hope it goes to where, what you're doing and, and what I believe is the right thing to do. But I, but for me, how, how big is, um, how big is jump crew?

How many employees you got now? 400, you said? Wow. 251. Like for me, I could do it, right? Cause I'm, I'm 20 people and I don't have VCs pushing down my back. I can, I can say, no, no, no. We only want to go after the ones we want to go after. But I guess where's the middle ground for you as far as scale of, of really doing, you know, what you need to, to get the numbers out there and personal and true connection, personalization. What's that balance for you? Um, you know, the idea of things that don't scale means that you have to define what it is that you're trying to scale. And I think that there's the default definition that scale means we're doing more faster when in all actuality, I think you have to decide if you want to scale quantity or quality, and you can scale philosophy, you can scale methodology, you can scale approach, and you can scale the network of people who felt they had a truly meaningful interaction with you and will remember that because I, my only expectation when I send a very specific custom email, or I record a video is of course, I hope the by-product is eventually a meaningful selling conversation, but I want people to see the name junk crew associated with deep, thoughtful work that was personalized and have them say, wow, that was, that was refreshing.

And that's what we believe in. And so if you can establish a foundation of that at the individual rep layer, then every rep that you add that still is bought into that same methodology and can show that although I didn't send 300 emails today, but I created five videos that are going to scale. I had one 60 minute conversation with somebody who's going to see your leadership position. And I said, you know, a demo with someone who's actually buying because someone who I emailed three months ago, who wasn't a good prospect, send them my information because I didn't spam email them. That is meaning. And it's just changes slightly the way that you define what you're trying to scale. What's up, everybody?

I know you're enjoying this conversation. John does a great job with genuine curiosity on these episodes and our guests consistently bring the heap. We want to take a moment here and let you know that you've got an opportunity, an opportunity to become better than you were yesterday. And you can do so by gaining access to all of JB sales content, all of their training tips, techniques, tactics, and takeaways can be yours for $1 a day. $365 for the year gets you annual access to everything, including our private Slack channel for members only, which you get access to all of us directly 100% of the time, 24 hours a day. And then at the same time, you're going to get access to our biweekly ask me anything sessions where you can bring real deals to the table and get the help that you need where you need it.

This is very, very important. Sales reps that invest in themselves are often found at the tops of their leaderboards. Join us today and get the help you need to become the seller that you deserve to be. That URL one more time is joinjbsales.com. Let's get back to the show with JB and our guest for this week. What I know you can scale is relevance, right? Because I can take a stab if I get down enough to some commonalities of certain roles, certain industries, certain things. I know some of the things, Jaren, you as a VP of sales are dealing with right now. You know what I mean? Just because I've talked to a ton of VPs of sales, I know what's happening in the marketplace right now and those types of things.

So I can take an educated guess on relevance and not have to be personalized. Because I say this all the time that the holy grail of prospecting, right, is personalization and relevance. But if you force me to choose between the two, personalization or relevance, I'm going relevance all day long. You know, we were joking earlier, like just because, you know, I went to the University of Maryland does not buy uni points these days. You know what I mean? Like, I still get those, hey, John, you know, terps. But relevance, and you talk about, we're on the same page as far as that real estate on an iPhone, right? Those first 10 words right there. We actually use, we actually ask a question. So I'll ask you a very thoughtful, direct question based on your persona in your industry.

So something like, hey, John, you know, how are you keeping your reps motivated and engaged now that everybody's working from home, right? If I would have noticed that you had to work from home policy or something like that, like, hey, how are you keeping the reps motivated and engaged now that everybody's working from home? And the goal there is to have you look at that and go, uh, why did you ask that question? Open up. Well, the reason I ask is because super relevant connection to that. And that's how we work together. So we're seeing a lot of that success. And guess what? You can scale that, right? Because, you know, for me, I'd much rather have you send me an email that asked me, hey, John, as a CEO of a sales training organization, how have you made the switch from onsite to remote delivery and retained your revenue streams?

Like that is an extremely relevant question you can ask somebody like me. And guess what? You can ask every other CEO of a sales training organization, the same fucking question. And so that's where we've tested that, that first sentence, like how to make it relevant, how to, how to not fake personalize it, but personalize it in a way that is at a bare minimum relevant, because that's the thing that they're going back to spam. The reason that most spam is, is painful is because it's irrelevant. It's something I could care less about. And so, but if it's relevant, all right. Right. So I guess for you, as you go to this, this next, I mean, and I love the idea, by the way, of everything being an experiment, because I'm on the same page right now, agility, agility, agility is the number one competitive advantage for everything out there.

So how do you, how do you coach your, your team or empower your team to come up with experiments? Do you have a framework where you say, Hey, I need you to have a hypothesis, a beginning and an end, a budget to it, a timeline, that type of thing. Or is it more of a little bit of a free flowing, um, Hey, whoever comes up with an idea, we'll coach you through it. Cause I think that's an important part of this is how to, how to give structure to experiments so that we can have them without losing control of them. From my own experience, um, the easiest way to keep myself accountable was to use a weekly team meeting as an opportunity to highlight, what did you try differently this week? Um, or show me an example of an outbound that you felt good about and let's socialize it with the team and what would find is that that became a living, breathing organism is that every time folks knew that they could experiment and that it would be showcased, then something from that email, no matter what it was, or that script or that LinkedIn message or that video they created would then get pulled from the rest of the team.

They go, Oh, actually, that is actually kind of a unique approach. I'm going to try a version of that. And so every single week you've got this prototype that turns into a, uh, a first version into a V2, a V3, V4, and it just keeps getting better and better and better. And interestingly enough, um, I actually just had this happen today. We do have a, what we call kind of our master generic sequence that if we feel that the list itself is viable, that we've had this Frankenstein of all of those different meetings that has come together over the years and that email still slays. And I got a response to, Hey, literally just somebody who said that is a good sales email. It was an all caps that that, and it's, it was, that was auto me like that, but it was automated as a result of human work like that.

You can't replicate that because the reps are getting the qualitative that the quantitative can't possibly get. So when I'm on the phone with somebody and I hear, Oh, that makes sense. So that really lands or hadn't thought about it that way. That's going right into the library and we're going to lean into it. And the value that you get from sales reps, feeling comfortable getting off calls and turning around to their manager, the director and saying, I keep hearing that this seems to be the problem or I keep hearing this common theme, how can we hit this on the head sooner, better or faster? Well, and that actually highlights another point, which is, I think the leadership needs to pay attention to, which is, I think so many of us, you know, the primary goal of, for instance, the outbound team is to get that meeting.

Right. So it's like all in, get that meeting, do whatever it takes. But I always said, there's a secondary goal to every single phone call you make and it's to grab that one extra nugget of information, whatever it might be, that'll help you learn and be more relevant next time. So for instance, right, you know, you talk about ideal customer profile and all these different things and all these little nuance, right? Like part of our, yes, we have the, this many employees in this industry is whatever, but we also have stuff like what technology do they use? Right. So if you're using sales loft, outreach, sales force, gong course, you know, all these tools, right? Like we know those tools and we work, we work really well with them.

And so I could call into a gatekeeper for instance, or whatever, and say, hi, is Sarah there? And, oh no, who's calling? Well, this is John with JBSales. The reason I'm calling is this is, you know, oh, let me put you through to her voicemail. Hey, real quick, before I go through her voicemail, do you guys use Salesforce? I'm just kind of curious. I'm just curious, right? I like that. And they'll be like, uh, yeah. Why do you ask? I was just curious, you know, I just, you know, blah. And then I go into Salesforce, I check out the box that says you use Salesforce. And then the next time I do get through to Sarah, I now have context to it. I now can reference something that I, that I quote unquote researched, but I researched it in a different way.

So I think that's the, the, the failure that I'm seeing with a lot of SDR organizations specifically is, is the hyper focus on meetings and the, uh, the lack of leveraging their collection abilities, if you will. Yeah. For insight. Yeah, absolutely. And that, that is a training responsibility. Um, that is a, um, CRM responsibility. That is a, uh, accountability responsibility from leadership to be able to enforce and empower that activity behavior. Um, and then, you know, I was actually just thinking, um, kind of what you're talking about that there's a direct correlation, um, between the scale of the organization to which you are prospecting into and the necessity for scale of your unique message.

Meaning if I wanted Microsoft as a client, I could spend days unpacking their whole org structure and trying to figure out who the exact person is. But if I created one of those videos and it was thoughtful about Microsoft and the opportunity I saw, whatever it may be, the likelihood that that's going to saturate into the little nooks and crannies of an organization that is otherwise pretty difficult to prospect into or much higher, whereas if my prospects are more the SMB, a mom and pop, a single location brick and mortar, that activity type isn't going to have the same impact because it's not applicable to that channel, to that buyer. And so I can probably just make a single phone call and more likely than not talking to the right person.

And so it just, it changes the approach. So, you know, you kind of think about it as like a sideways little funnel, you know, the bigger the organization, the more your message is going to have to scale to get any chance of visibility. Yeah. And I think that's the, you know, I, we always tear out our accounts, right? You got your good ones, your average ones, and your shitty ones. And that to me is, is their approach. Like the good ones, that's, those are the ones you take your tailored approach to. Those are the ones you spend homework, you know, time doing homework on. And then the, you know, the small ones, like that's where you kind of have to do volume. It doesn't make sense to personalize every email to a SMB audience.

Right. Um, so how do you encourage, or what's your, I guess, what's your philosophy on with this experiment model that, that you have, um, of trying things out on a regular basis, what's your encouragement or disencouragement of failure? And how do you, how do you approach it? Um, like when one of these experiments fails, I can, I'll explain it slightly differently from my own perspective and then how it applies here. So, um, uh, outside jump crew, I do some, um, I do some real estate investing in the properties that we buy, need a lot of work. Like they are, you know, really low, you know, really need some, some, some effort. And, um, pretty recently we got hit with a very large bill to completely repair an HVAC system, like had to completely repair a whole HVAC system.

And that's like, I hated getting that bill. And, you know, at first the knee-jerk reaction was like, God dang it, that sucks. Like this blows, what am I doing? It's so dumb. And then I had a brief moment of clarity and I told my wife, I was like, you know, this is that, this is one of those moments that somebody who eventually becomes an expert at doing has to go through to ultimately become an expert. You have to experience this moment so that next time, you know, like, Hey, maybe the next property, I will want to buy something that has a new HVAC in it. Like, and I can't get better unless I felt that pain. And so I think that that directly applies into that experimentation mindset is I remember us trying to really get creative.

And I had a, one of my reps was writing poems. He was writing like custom poems, like haikus, like, and they were good. I was sitting there laughing my ass. How creative and fun they were. I remember him doing one for, he was prospecting into weed maps and like, he was using all of these different strains and his, it was hilarious. You know how many responses we got to those? Zero, zero responses. And so he could take a couple of different, um, you know, passive reaction that he could say, what a waste of time that was like, I'm terrible at my job, whatever. I said, look, you just created a little library of hilarious content. I said, don't tune that into a LinkedIn post, like all of those in anonymize the prospect and put your entire now, um, um, um, anthology, your, your, your chronicles of your poems.

Like you just wrote a book, dude, like that's amazing. And people are going to love that. And like you now know that that's not the best way to go about it, but you flex that muscle so much, that's just going to become part of your DNA now. And I think that's right. So I'm, I'm all about failure as long as you learn from it. And that's why I encourage, you know, everybody, when I do trainings, talk about, I talk about AD split test, everything, because, and the basic example here is if you make 50 dials in a day, right? So you make, let's just use a cold call example. If you make 50 dials and you get no meetings, it's a shitty day. It's demoralizing. You, you, you go home questioning why the fuck you got into this profession in the first place and everything else.

But if you make 50 dials and you split them up and you do 25 and 25, right? And you test each message to a similar profile group. So you're actually looking at, you know, you're not just calling dialing for dollars for anybody that's in your database, but you're calling for instance, every VP of sales and SaaS, right? I'm going to call 25 dials with this approach and 25 dials with this approach. Even if you still get no meetings, to me, that's a good day because you just figured out two approaches that don't work and tomorrow you'll find a, you know, and the more things you find that don't work, get you closer to something that does. So I guess the question though is, and you're closer to it than I am is, you know, I think a lot of like, and maybe I'm talking like my dad at this point, but I feel like feedback these days is hard to come by as far as like, you have most, most of the generation that I've come across is like, they don't, they're, they don't take feedback well.

They don't know how to get feedback and they're afraid to fail. Are you, and I think this goes back to your hiring profile, but do you see this in your, in your hiring and what's out there? And how do you test for somebody who is, you know, in your interview process, if you will, who's coachable, who knows, you know, who's, who's likes feedback and, and those type of things. Cause I, I, I'm finding it rare these days that it's, it's welcome. Let's put it that way. Yeah. I can't say I have a silver bullet by any means. Um, you know, I don't have a playbook of how to, how to perfectly hit that every single time, but certainly in the interview process, things I'm looking to hear are, um, I like to hear folks who have tried to do something on their own, even if it was something simple, I remember a rep that, um, he said that she does, um, uh, what do they, when you do shoe cobbler, he was a cobbler as a, as a hobby, right.

Of all that, he literally put shoes together. And like, I'm thinking, wow, that's a fascinating B is unique C it takes a combination of, you know, um, thriftiness and, and, and manufacturing and patience and all of that. Like that's, that is a, um, soft skill indicator for me. I mean, there's the kind of cliche, um, interview questions, like tell me about a time where you failed and all that, you know, you may get some lip service in those answers, but like directionally, I think that that gets you there. I think as sellers too, you know, this is a pretty objective performance based role. And so there's gotta be all this, there's just this pressure. It's like, I have to produce the result and I don't have time to test.

Like I got to find results quickly. And so finding that balance is an art and a science. Again, I don't have a playbook for it, but I think that an organization and something that I'm very proud of at jump crew that can foster, um, experimentation with the end result in mind, like not at the expense of driving outcome, but knowing that as long as we're sticking to some of those static elements that we know are true. And as long as we're empowering a sales team with as accurate, um, and specific and intentional list of accounts as we possibly can. And they know the guardrails of, you know, what's appropriate and what's not like, yeah, encourage them to play around. I like your methodology. We're saying like, let's create, you know, three or four different sequences where the static stuff is the same, but let's play around playfulness, creative, um, the corporate E like, let's see if one of these resonates because we know a constant in this experiment is the prospect profile is basically the same.

So that, and so that jumper believes that through, through our clients see that, you know, they see that they, they think that what they come to us is just for the sales, the end of the sales. Right. And of course that's, that's what they're going to, what they'll eventually get, but finding a thousand ways, how not to do something means that they then have a playbook at the end of the day that they can use in perpetuity and, and it takes experimentation to get there. And we have to be the champions of that from the rep up. Yeah. And I think that to your point of like balancing results and, and, you know, experimenting, it's just fail fast. You know what I mean? Like, like let's, and it's, it's not like a three month cycle that we're running this experiment through.

It's like, you know, I tell people right now that like, I don't know about you, but I can't see past shit. I can't see past next week at this point, but I can't see, I definitely can't see past Q1, like you can't tell, there's not a leader out there that can tell me with confidence that, oh, Q1, we bought, we're bottling out on this, you know, recession here. And it's definitely going to go back to Q2, Q2, we're going to be okay. Nobody can say that, right? Because who knows? I mean, Chad GPT four is coming out and we might all be replaced for crying out or five is coming out. We might all be replaced, whatever. So right now, agility, experimentation, fail fast, move. And I don't know the, the challenge though, and we'll finish on this is it sounds like you are cut from a similar cloth of me is like, I actually enjoy chaos.

I, I, I thrive in it when it, when it's, when it's, I don't, I get bored when things are stable. I get bored when things are kind of, and I just kind of end up farting around and doing stuff that I probably shouldn't do being inefficient. But when it's fucking go time, man, I'm all in. Like, I'm like, oh, let's go. But that scares a lot of people. You know what I mean? Like, I think the majority of people are risk averse. They don't want, they like to do what they've been told to do. They like to fit into this little box. And so again, I think it gets back to, to, to hiring profile, but I think people have to be very comfortable being uncomfortable moving forward. Cause I don't see it getting any, any easier.

I think it just getting more chaotic, more stress. I mean, think about people like, oh my God, like COVID that fucked everything up. You know how much shit has happened since COVID that's been fucked up? Like massive amounts of shit since COVID have been fucked up. And it's only been three years for crying out loud. It's just going to get weirder. So can you coach to adaptability? It's a good question. I don't know. It's a good rhetorical. I don't know if you can, you know, I, I think that it comes down to some people need to be cut from that cloth. Then you have to be able to identify that. Um, I don't know if you can coach it. I think people can evolve into it. I don't know what the framework is for coaching it, but I certainly do believe that if for no other reason than for the catharsis of just doing something different to blow off steam, like in an, in a, in a, in a, in a responsibility in sales, where if you aren't doing that, like it can feel like groundhog's day every day.

Like that is a, a release foul for sellers to say the very least blow off some steam by just trying something unique to you. We, we had an AE who was great at ukulele. I said, write a song and he recorded a song on ukulele and sent it out. We made a whole video about it for jump crew corporate, like put those people up to be their best selves and at the very least let them, you know, release the valve at the very best, have some meaningful connections from it. Yeah. And I think that you just got to get back to having some fun with this, man. I think people take this shit too seriously. I really do. Like people are like, oh, you know, cold calling. I'm like, what's the fucking worst thing that could happen to you on a cold call?

They hang up on you. Shut up. Get on the phone. Yeah. Like have some fun. Stop being a robot. Absolutely, man. Awesome, man. Well, let's tie this up, but I appreciate this conversation. Why don't you, John, tell people where they can find out more information about you, about what you're working on, jump crew and everything else. Yeah, definitely. So you can check me out on LinkedIn, jump crews, www.jumpcrew.com. You can look at some of the other interviews that I've done and some information about me at jaronbosberg.com. I'm relatively active on LinkedIn and I'm always happy to blow off some steam with some other sales folks if they want to get anything off their chest. Love it. And for those of you listening, it's Jaron, J-A-R-O-N, J-A-R-R-O-N, Bosberg, V-O-S-B-U-R-G.

And it's jump crew, all one word. Check him out. Go see what he's up to. He's doing some cool creative shit out there. And Jaron, thanks for coming on, man. I really appreciate it. It was a fun conversation. It's been a blast. Thanks, John. Absolutely. And everybody else out there listening, as I always say, go out there and make somebody smile today. Because no matter how bad your day went or you think it's going, you make somebody smile today and 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'll see you on the other side. Thank you so much for your time today and listening to the podcast. I hope you enjoyed the conversation as much as I did.

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