Make It Happen Mondays Podcast
November 2, 2020
This episode is a conversation about how a sales rep at Proposify built a reputation internally for positivity, humor, and cross-team collaboration despite a tough sales year. The discussion covers finding good client fit over closing at any cost, using humor to build rapport and ease into harder conversations, and building a personal brand through consistent, authentic content.
The episode features a Proposify sales rep discussing how staying positive through a difficult sales quarter, prioritizing good-fit clients over quick closes, and using humor helped build trust with prospects and internal teams. The conversation also covers personal branding on LinkedIn and how authentic, consistent content performs better than overly polished posts.
Closing deals with clients who are not a good fit can lead to churn, damaged reputation, and higher long-term costs in both labor and emotional strain on the sales team. The guest argues that flagging poor fit early and sharing that feedback with the broader team helps the company improve its product and avoid repeating the same mistakes.
Humor and lightheartedness help build rapport quickly with people who have never met you, which makes prospects more comfortable and willing to trust you. It also creates an opening to shift into more serious or uncomfortable questions, such as asking what a problem is actually costing the prospect, once trust has been established.
The advice centers on getting started, posting consistently, and connecting content to genuine personal interests rather than overthinking production quality. Authentic, sometimes unpolished posts, including honest templates or candid moments, tend to resonate more with audiences than heavily rehearsed content.
A conversation between John Barrows and his guest, recorded November 2, 2020. This transcript is machine-generated and will contain errors. Where it disagrees with the audio, the audio is right.
What's poppin' y'all, it's your man James, Say What Sales Buckley, and welcome to another episode of Make It Happen Mondays with your host, well, it's me today actually. This episode as always is brought to you by our incredible sponsors, Sales Loft, Gong, Vanilla Soft, Vidyard, Proposify, Zoom Info, Loom Cube, and our newest partner, Rise. Welcome to the family y'all. So here's the deal everybody, our partner Proposify does a great job recognizing exemplary employees because of the results, the merit, the attitude, the mind frame, collaboration, and positive impact that their employees have on the team. So I was excited to speak with Scott York about his impact that he's had over at Proposify.
This conversation was so electric that it needed to be shared and we thought the perfect audience is the Make It Happen Mondays listeners. Scott's attitude, positivity, and communication internally led Proposify to connect them with us so that we could get this conversation to you. Let's turn it over and get started. Scott and I hit it off right away, long before the broadcast started. So we're going to dive in to this burst of energy that we call a podcast. Make it happen. What's popping, buddy? How are you, my friend? James, I'm well. How are you? Dude, I love you already, dude. This email that I just got with everything that you have done in Q3, like you and me, dude, we are the same. We are when two become one, my man.
No, Voltron style. Like this is about to go ham in here. Oh, yeah. We're going to have a lot of fun. How the heck are you? I'm fantastic, dude. This year has been both challenging and probably the most rewarding year that I have had in my sales career. How about you? Nice. I mean, I just want to say, tell me more. Typical sales professional. No, tell me more. You have my attention. Yeah, exactly. No, it's just been different. Like, you know, I think the SDR role has been forced into like finding other avenues of value that they can provide right now. And some of us are gravitating towards things that we like never thought were an option for us coming into this role. It was like, okay, you're going to be just like Morgan and you're going to train and develop.
And, you know, I thought, oh, man, this is like everything I've ever wanted. And then I started working with the CRO, Chris Merrill. And we started learning about all these other different things. And I was like, dude, there's so much more here than what we think there is when we are an SDR. So just like looking across organizations and seeing lots of different avenues of revenue generation that really like promote positivity is a completely different outlook for me. And I couldn't embrace it more, I think, at this point. Sweet. I should know this. I mean, from LinkedIn. But how long have you been with the team? I started in December of 2019. And my like big welcome to the team, if you will, was COVID.
Well, so no, actually, this was like, so December 2019. So three, four months before COVID, right? Yeah. But my, hey, this is what we're going to do is welcome to the team, build your course for personal branding, and then let's go record it in Las Vegas. Wow. That's sweet. So I was like, oh, man, this is crazy. Been to Las Vegas many times. But then, you know, coming into then COVID happens. And it's like, all right, everything that we had planned for 2020, we'll just chuck that. We'll just throw that away. It's completely meaningless now. And let's just make it through the year and do incredible things for the community and help as many people as we can. And that's kind of been the goal. And it turned out that that was exactly what the community needed all the time.
So that's amazing. Just a really strange, like, ramp time, I guess. Yeah. Yeah. No kidding. No kidding. Yeah. No, it's been a good year for me. You started at Proposify, like, when? Just in March. Yeah. Just after COVID, if I'm not mistaken. Yeah. We were a little legged in Canada. And we're on the East Coast. So we're smaller. We're like the New England of Canada. So smaller population, a bit sheltered from, like, the Toronto-Montreal situation right now. But, yeah. So I was in the office for two weeks. I started on March 2nd. And March 13th was the day that they said, you're probably not coming in Monday. Like, take your stuff with you. And so, not in a, like, your first two weeks went horrible.
You're fired. But COVID is most likely happening. So, yeah. It's been wild. Like, onboarded pretty much fully remote. And it's my first time in SAS. So I came from, not to get into my resume, but came from a pharmaceutical background, both as a, literally, like, a pharmaceutical rep for a manufacturer for years, and then worked for a vendor that sold services and patient programs to big pharma. And so, I was in a new industry, in a pretty new role. And, yeah, man, it's been a whirlwind. I've taken a lot. I've grown so much, like, selfishly, development-wise, grown way more than I expected. But Proposify is a cool company. Like, we're still in an exciting but frustrating time, trending in the right direction, learning tons.
But it's been fun to be part of a local company that's changing fast. And the feedback we get on the front lines is directly taken to where we're heading, which is cool. Yeah, we've been big fans of working with you guys for a while. One of the coolest teams to work with as far as, like, communication and, like, you know, direct about, like, what this looks like and how we can work together to make it the best, right? Like, I feel like there's a huge focus with you guys on quality. And I think we have the same focus on quality. So it's really been great. The story that I got about you was about embodying all of the core values at Proposify. So I really want to kind of get your Q3 experience because the stuff that I read about you was, like, I felt like I was reading about myself.
I'm, like, a hopelessly positive person, generally speaking. I feel like I can't help but see things like silver linings and give people, like, this perspective of, well, it could be a lot worse, right? Like, so tell me a little bit about your mentality for Q3 that prompted them to be, like, you guys have to meet Yorkie. Oh, where to start? It was a bit of a blur. Honestly, it was frustrating, man. Like, I'm with you. Like, we're on the same page. I'm a super positive guy. I have sometimes the analogy of, like, you know, the duck paddling, and it looks kind of positive and cool on the, not cool, but you know what I mean? Even keeled on the top and underwater, you're swimming to beat hell. So, yeah, there were some frustrating deals.
As you know, like, we're really trying to make the move up market towards that mid-market fit. And we're not quite there yet in terms of product market fit. We're, we've made big strides even since I started, which is exciting, but have had a number of significantly sized organizations with really good fits where, you know, for whatever case may be, just fell a bit short. Right. And I'm not putting it all on the product team. There's certainly things like self-reflection wise that I could have done better. Yeah. Change that criteria, reprioritize all of that. But I think the silver lining, the positive, and maybe why I was recommended is that I've always been someone to, sure, the back of the jersey is important.
I don't know if you're a sports guy, but I really play for the front of the jersey, like first and foremost, and understand the value of good fit clients, the value of going through and understanding why they may not be the right fit now and sharing that back to the team so that we can get there faster rather than bring them on board, on board them six months or a year, they churn, they're not happy. It's damaged our reputation. We haven't learned from it. And I think that's maybe why it caught me off guard, to be honest. Um, uh, you know, not that it was an Oscar, but it was like coming feedback from the product and marketing team. It was like, Hey, I, this feels good. So, you know, you touch something there that I think is super interesting.
And this reminds me of a recent episode of muffins with Morgan, where Meg Holsinger, our customer success director, who is a phenom when it comes to customer service and retention and just providing a good experience overall for people that are a good fit. Um, uh, she's amazing at this and she talked about what you're doing when you close an account and not consider what that's going to be like after that close. So there's this element, I think of the overhead of selling a deal. That's not a great deal to begin with and having it be a lot more taxing, both from a financial perspective, because the cost of labor to maintain that account over the course of a year is pretty extensive. But also from an emotional draw perspective, like the stress of having an account that is not happy with your product after spending thousands of dollars on it.
And in some cases, hundreds of thousands of dollars on it can be very overwhelming for salespeople. But everything I'm reading about you leads me to believe that you have this ability to find the fun and the humor and the lighter side of that. So dive into that a little with me and tell me why you think you have that gift for that personal experience and positive light. Um, you're full of good ones today, James. Um, I think one, I love that point about the customer success, customer service piece. Yeah. I think what may be a little bit unique about my background is that I, I didn't, I came from an account management background. So my, my last role, I talking about personal development going from like pharma drug rep, you know, carrying the bag, going into docs offices, like, you know, the 2015 version of love and other drugs, right.
Which is not nearly as glamorous as that. Uh, but, um, into my role in my last company where I truly was new, like more of a customer success manager in a sense in that we had a finite amount of. Clients, right. There are only so many pharma manufacturers. And so the bulk of our business was land and expand or retain and expand. Right. I'm sure there were some new business, but I was doing a lot of customer success type work. And so I think right out of the gate, when I started with proposal, if I meet the folks on our customer success team is like, listen, I, I've been in the position where the client isn't happy. Um, they, the service for whatever reason is falling short, it was on me to retain them and to work with the appropriate department to get the product where it needed to go.
So I think I have a, maybe a unique aspect of empathy for that team, which may make it more top of mind when I'm trying to close the good deal. You know what I mean? Yeah. So through all that, getting back full circle to the positivity, I think it's just, some of it's innate. Some of it is just like the, the willingness to trust that there's such a good team here of good people heading in the right direction across the board that like, we're getting there. We're heading, I've seen such good progress and it's like short-term frustration and pain. Like, yeah, I've hit this desk a few times, like a hundred percent I have, because things were so damn close with deals that were triple my average deal size since I started.
And we fall a bit short from a bit of what I've done, a bit of what we can't yet do. Um, but it's like, Hey, we take that feedback. We get there. Their experience was positive. It's just not a fit now. And I think knowing to your point, James, that the whole company's not going to be not the whole company, but, um, it's not going to be an anchor for the folks mentally, emotionally, financially, it allows them to get where you need to go. Yeah. Right. Sorry. That was long winded. No, I listen, you're hitting the nail right on the head there. Like we're all heading somewhere, you know? Yeah. It doesn't do us any good to focus on the agonizing journey. That is that travel experience, if you will.
Uh, I think it does us good to take our time and really look at what we're doing and have it be meaningful more than anything else. Um, for me, meaning has a lot to do with the way that emotions are attached to our processes and the way that we treat others. Um, everything I'm reading about you has a humorous note to it. Uh, you tend to have a funny bone and I am very attracted. Like it's a magnetic thing for me. Humor is universal. I use it all the time. Um, use it in the sense that like my love in life, my joy in life is to make other people laugh. My wife will often say that that was one of the dominant things that had her attracted to me in the first place was that I make her laugh. They say it's hard to be in a conference room with you and not laugh.
So I got to go with it. You got to give me your best dad joke right here. Oh my, oh man. Best dad joke. Oh, wow. I mean, I've got it. Listen, I've got, I've had dad humor my whole life, but I've only had almost four years to really cash it in as dad humor. I've got a son that'll be four in January and I've got a six month old little boy. Yeah. Um, so, um, best dad joke. Uh, let's see. Um, you might have to leave that one with me. Oh, wow. That's all right. That's all right. Hey, it's okay. Uh, one of the things that I know about humor that I always tell people is like, I talk to a lot of people all over the world. I'd imagine you do too. There's a lot of people outside of the U S and you never know what they're struggling with and what they're dealing with.
But what I do know is that people like us that have a lighthearted nature to the conversation tend to kind of take away the, the stress and the anxiety of meeting somebody new. Uh, I want to know what that's like for you and your day-to-day routine. Like, you know, you're somebody that's being recognized as not only productive and able to get results, but also this uplifting personality in the office setting and on the team. And in this virtual world that can be really challenging to accomplish. So they refer to you as their own Conan O'Brien. And I can see now why with the red hair and the facial expressions and obviously your incredible shirt there. Tell me, tell me about how this day-to-day works for you and what that looks like from a engagement person, like an engagement back and forth with a prospect when you're trying to make this a very easy, lighthearted conversation.
Yeah. So, I mean, I guess the first and foremost, I've just like you, I've just always loved connecting with people. And to be honest, that's sometimes the tough part of the nature of, of working in this role as an AE in SAS with Proposify that's a shorter cycle is that I'm, I said, I come from an account management background. So I'm used to that ongoing relationship and it's like, it's speed dating, right? We've got 30 day cycles. It's like, you know, book them and move on and you meet the new person and you try and win them over. And I mean, I guess it ties back a little bit to the humor. Of course, there's some folks you get on the line that, especially in the first call, they're not really feeling it.
You got to get right down to business, but I just have ridiculous sayings. Like I grew up in a rural area in the East coast and, you know, whether it's as handy as a shirt pocket, whether it's, you know, um, lighthouse in the fog as your foundation for your proposal, uh, best practices moving forward. Like, I feel like I just have East coast isms that have been like woven through the fabric of my Conan shirt that it's, I'm not even trying to be funny. It's just like the, the, the sayings that I pull out and have no problem doing that on a prospective client call. So it's like, I love making analogies. I love, um, trying to relate. If I know someone's a baseball fan, I'll talk about it like a closing pitcher.
Um, so I think from a, from a humor and a positivity perspective, the thrill I get is building rapport, um, with someone I've never met is gaining their trust quickly. Um, the challenge with being so positive, and I'm sure you face this all the time is being comfortable asking the tough negative questions, which I've had to be very intentional with. Like we're problem finders, right? We're problem solvers. So I have a natural tendency to say, Hey, James, like, what are your goals? What's your blue sky? Which is a great question to ask. But at the same time, it's, you know, what's that costing you today is a little more uncomfortable for a positive person. Right. But it gets to the root of what's actually going on.
That's true. And, you know, I've always found it challenging and tell me if you feel this way too, there is a challenging nuance and kind of a behavioral shift that takes place in somebody. When you go from this very lighthearted conversation to something that's causing pain in their day to day lives there, you can visibly see the way that their body changes, their nonverbal cues change when you bring something like that to the table. So there's, you know, like you and I jumped on the call and it was super vibrant and happy and everything. But the moment we start talking about our day to day routines, our excitement kind of takes a little bit of a dimmer almost to it. And I think that's because the connotation that we have in our minds about work in general tend to blur how our emotions are reacting and causing us to react to our actions every day in an eight hour, 10 hour, 12 hour day of sales, which is, you know, hours of rejection and a few happy moments.
It's kind of like the nature of what we do is high rejection, low acceptance. And I think there's a special type of person out there on every team that's able to just like lessen that blow with the way that they react and the way that we talk to people. And I'd love to get your thoughts around what that looks like internally in the virtual world, because I know you're on Slack probably all the time. If you're like me, I probably post like funny things that you see in like the general channels. I'm bad about that because I feel like that lighthearted nature kind of takes away the serious tones from the way that the business, the typical business conversation would go. So tell me, like, what's the last thing you posted in Slack that was funny?
All right. It was, it was yesterday and we've got a, we do a power hour. So as a team, we're doing outbound dials, right? And this isn't even that funny by the way, but it got a, it was dad joke category for sure. Um, and, uh, and so I, yeah, I spoke with this VP of sales and classic, right? He was like, yeah, you know, talk to so-and-so about that. And I pushed through and I was like, listen, if I reach out to her, Alexis, like she's, she's never, I'm not going to answer. Like, so like, how, how can you help me out if you say there's room for improvement? Like anyway, so anyway, I posted in, in Slack and was like, Hey, I just got a great tip to email Alexis, um, and have this guy, Mike essentially give me kudos or like give, say that we spoke and that she should listen to what I'm saying.
And I just said something stupid, like not to be confused with Alexa, right? Like, and like, again, super dry, not that funny, but just like little, little quips like that, that I'm always tossing out. Like puns, uh, are, are very much present in my humor. That's good. Yeah. I, uh, you know, I think that I, I say, what language do you laugh in? You know, that I got that from a rapper, brother Ali is, is his name's great rapper, but there's this, there's a couple of different songs he does that have like really impactful statements for me that I like to highlight and what language do you laugh in is kind of what resonates with me when I talk about how to use humor in sales, because when you're like us and you sell technology, we're international, like we can sell to anybody.
If I'm up at two in the morning because of my allergies, I'm usually down here with the sniffles talking to somebody in India that's been at work for the last three hours, four hours, you know? So that's like, you know, I want to be able to have those lighthearted conversations and make that connection so that I can earn the right to have a conversation that's a little more serious. Uh, and I think that is really a skillset that takes a specific, what's the word background? I don't know. Um, but the same thing is sort of relevant to the way we work internally. Um, for example, one of the comments that was made about you was the way that you worked with the dev team and the product team, you know, those two departments, sales and product very rarely cross paths.
So I would love to know what it is about the conversations you're having that are prompting you to go back to development and product and say, here's this customer. Here's what I have. This is what you need to know about what they're telling me. We need to make some changes. What prompted this? Like what kind of conversations are you having and how are you drawing those lines to value? Yeah, I think, uh, I think it's a good point. And I'm not surprised to hear that they rarely merge, right? It's not like they're oil and water, but in a similar fashion where sales and marketing have to be perfectly aligned yet at times they're so disconnected, right? In organizations. Um, I think one thing is just like the, the sincere desire for this company to succeed.
Like, and I, and I mean that across the board, like I came on board, I was fired up, you know, chatted from Kyle all the way through, um, and I believe in the products. I believe in where we're heading, the pain that it solves I've experienced before. And also on the sales front, I really want things to be a good fit and a big win for these prospective customers that some of which have came to us through inbound, some of which we've done, uh, you know, the team members have worked their butts off to get them on the line in the first place. So if we do fall short, I think it's just drive to want the product to get where it needs to get to, to align with what our ideal fit customers are. Right.
So I also think it's just the cross-functional nature. Like I worked in higher education, cross department stuff. I worked in pharmaceutical, cross department stuff, and I just have no problem just reaching out and having a conversation. That said, they're also very encouraging about that feedback. So it can't, it can't be remiss that they are wanting that feedback with open arms as well. So we're consistently being encouraged to bring that up, to bring our chief product officer on calls. Right. Having an open door policy there seems like a great move. And it's interesting to me, we make all these channels in Slack, right? And I think, I think companies that sell products are specifically guilty about this.
They make all these different channels in Slack and they silo the communication by adding members into Slack channels. And then that's a separate conversation. And if nobody that's on the front lines of that particular outcome is replying in that channel and giving feedback, it's kind of blind if you think about it. And I think a lot of companies are guilty of siloing these departments in Slack or in other channels that they communicate in. You know, we do a big email chain to the whole department. Well, that's great. But other departments might have some input that could be impactful for that department. If you only silo to that department, what you're really managing is this little tiny cell that affects everything else in this giant industry or this giant company, this bigger, this bigger boat.
So like, what's that like going straight to product as a sales professional? I got to ask, like, do they look at you like you're knowledgeable or do they look at you like a lot of product people look at salespeople and go, I have no interest in what you're about to say to me. I'm busy working on this project. Salespeople do the same thing to product people when they come to them. We're deep in our pipelines. We're reaching out. This product person comes and we're like, I can't even talk your language, man. I have no idea what you're saying to me. Like, what does that look like for you guys? You know what I'm talking about. I know exactly what you're talking about. I think it's picking and choosing your battles.
Like, for me, it's realizing that there is a consistent process in place where we're consistently streaming, whatever, call it a feature request, right? Or something that comes in that a prospective customer wants and they're aggregating that and they're analyzing what's high priority and what's not. But if something's so close, I'm not picking up the phone and calling Ricky up like every other day, right? So I think they've realized that, and don't get me wrong, I was probably doing that a little too much to begin with and they were starting to tune me up, right? So it's like, okay, Scott, like you got to filter yourself. It's like, you know, round two with my wife being pregnant. You have a couple of extra layers of filter.
So you know the words don't actually leave. Learn that the first time around, right? Yeah, it's like that one got out the first time and it didn't end well. And so my product filter, I feel, has been built up maybe the second with this, call it like second half of my first year. And so they're more willing to listen, right? They're like, hey, the points that's been raised, it's sincere. It's client-centric. I just try and be client-centric all the time because I, and it's not a mask. It's, it's really who I am. I want them to be happy when they're signing the proposal. I want them to be happy and, and continue and not churn with the CST, right? Yeah. Yeah. So you can't tell me you're not feeling the energy off of this episode.
I feel like it's going really well. Be sure and submit your sales wins to james at jbarrows.com. Today, we are highlighting Colin, a recent JB Sales On Demand member who's using the structures, techniques, and tactics in filling the funnel to prospect his way into a new sales job right out of college. His investment in himself led him to a career opportunity with a reputable tech company in the SaaS space. Stay the course, Colin. We got your back. So I want to thank you for coming out and meeting with me today, man. I know that salespeople have a hard time finding the time. What can I do for you? How can I be valuable to Scott? Gosh, man. That's a great question. I mean, I, I've been learning so much from, from the, the, the community already that you guys are a part of just in terms of this partnership.
So specifically, um, I don't know. I'm, I'm, I'm wondering on feedback from your experience, like the, the world that you're in knowing our product, knowing a bit about where we're heading, like what, what are some tips that you see to, to keep raising that personal brand? Like I, I've been battling first and foremost, like talking LinkedIn. Um, I just, I made a post today. Like I've had like a month hiatus, like it, this content creation is new to me. I'm not a big Instagram poster, right? I'm not a big Facebook poster. Yeah. So LinkedIn, that's, I just kind of talked myself into a circle. See how I did that. I was like, something's coming. I got to get there. Um, and so this whole content creation on LinkedIn is new and I've had some fun with it.
I'm trying to find my lane. I want to be sincere, right? I know my, the content I put out in the past has landed, is relatable, is funny, but yeah, any tips on that to keep the fire lit, to keep the momentum high? Uh, so let's talk about that for a minute. First of all, um, you definitely want to go on my LinkedIn and check out the video I just posted because you can access the personal branding course for free right now. And that's important because it's going to give you the nine things that it's a nine part series on how I built say what sales, um, say what sales is what my personal brand is. And I started that back in 2016, my second year as an SDR, I started to create content around what my thoughts were and my journey so far and things that were working, things that weren't ideas that I had and, you know, concepts to draw lines to.
I used to be a cook, so I made a lot of food references. I attached to myself to being a foodie and a beverage person. I came from the restaurant industry. Oh, like cocktails are a focus for me, you know? And I attached myself to these bigger concepts of things that I could post about and talk about. And it drew people in towards me. And that was a great connector for all the things that I did, because if you're in business and it's, and you like happy hours, you might see my posts and give me a like, then I have a green light to reach out and have a conversation with you. So leveraging my consistency in content and different macro concepts, things that people liked, that was a big driver for what I was doing, which was essentially just trying to have as many new conversations as possible every day.
So I knew that if I just attached to myself to the right things and constantly had stuff to talk about, you know, I'm a huge hip hop fan. So for me, writing quotes from rappers that are like inspirational and kind of tied back to sales. That was the birth of hashtag hip hop and sales, which became like a whole thing. There's like people out there that do actual freestyles now because we started doing this hashtag hip hop and sales thing. And people are starting to like do things back. So I came up with a catchphrase. The point is, is that I went on all of these different mediums and started to create the types of content that I thought would resonate with that sort of medium. And I didn't limit myself to one or the other.
So you're like LinkedIn content is new for me. What I'm telling you is that content is new for you. Period. The end, go learn how to do all the different types of content on all these different mediums. And what you're going to find is that your social presence is like a living, breathing thing that attracts others to you. And you have to make that happen so that people will want to talk to you, which is 90% of sales. How do I make this person want to talk to me? I cannot tell you how many people start a conversation with me on Instagram. And they're like, James, huge Irish whiskey fan. I see that you are as well. I would love to connect sometime. And you're like, what does this person do? So you find them on Instagram, you get their full name, you find them on LinkedIn, you find out their VP of sales at GE.
And you're like, whoa, this is like an actual somebody, right? And you're like, all right, let's connect on Instagram. They will go to your LinkedIn calendar or your calendar link and schedule a call. And then you're in this call like, hey, thanks for the follow on Instagram. What's your favorite stuff that I do? And he's like, oh, I love all the cocktails that you post. That's awesome, right? Like, how could you ask for a better introductory call than somebody that likes what you do? Yeah. Yeah, that's a really good point. And there are some threads woven through the content I've put out. And again, there's the, you know, getting started, which I've gotten over that hump. There's the consistency.
There's the frequency. Yeah. Of course, right. And then, and of course the content that's driving it. And I'm a big quality over quantity guy. So I think that's where I maybe overthink it sometimes and get stuck in the mud. But, you know, kids are important. Yeah, go ahead. Yeah, best thing. Yeah. Morgan will tell you that when he first started creating content, one of his biggest like downfalls was that he was constantly doing like multiple takes, trying to get his words right, trying to slow it down, wait, that's too fast. I tripped over that word there. My background is not good, right? There's a lot of things that we can do that really are just our insecurities coming out, right? That's all that is.
If we can make it over that hump, it's super easy to just turn your camera on and one take Jake it. Yeah. And people appreciate that authenticity so much more than the clearly rehearsed eighth take of a video where you're like, duh, duh, duh, duh, duh, duh, duh, duh, duh, duh. The same thing happens in writing, right? It doesn't have to be a big giant novel or a, you know, huge white paper with lots of images. A simple post that resonates with your audience will go a long way. I remember the first thing I wrote that went viral, this is where I got like hooked on content. But like the first thing I wrote was like a joke template that I came up with, with my supervisor, my biz dev manager. I was like, wouldn't it be funny if we were just honest with our prospects and we could write a template that was like, dear person, we can do this dance for like nine months where I reach out every two days and bug the hell out of you.
Or we can find 10 minutes this week and figure out if we're going to be a help for you. Let me know which one you'd like to do. Talk to you soon. Like that was the template. That is brilliant. The next day I got up and came in 219,000 views, like 400 shares, like thousands of likes, hundreds of thousands of likes. I had DMs from people that were like, I've been the genuine recipient of this template four times today. Another set of people were DMing me. Like I set four meetings today with this template. You're like, what? Like I was just saying, but that's where the, that's where it becomes like super obvious to me that the goal is not to pester people with constant outbound shit all the time.
It's to yes, be calling to connect. Yes. Be reaching out to set some kind of conversation in place, but also to provide value to a community that draws people towards you and wants you to have that conversation with them. I have many instances where I'll put a post out about a solution that I was offering and someone will comment and be like, I just had a meeting about this. I'm DMing you now. And then you see that DM come in and it's like, James, when can we connect? I just talked about this with my team. Like, yeah, that's amazing. Here's my link. I'm looking forward to it. And before you know it, the momentum is there and it's so easy that way. And all you did was be honest about how you help people.
Yeah. Yeah. I guess the big question is like, how do you get there? Right? Like you spoke to it a bit about, and, and I've, I've reflected that in my content. Like what's important to me, my, my kids are important. I'm a family man. I'm proud of them. So I've taken some funny things that have happened in my life as, as a dad and, and with my, my boys and we'll start off with something funny, whether it's a story about the gingerbread man and it's like not rushing to a proposal. Like I love making those analogies, right? Like the sports playoffs that were back in action and like, you know, getting fired up for your day. Um, so I, I see the enjoyment that comes from that and the, the, you know, posting something funny, like the, the biggest image, like the image that landed the best on my profile was me where I had a film review with my team and it was an absolute dud.
Like it was like embarrassing. Right. And there was just a picture of me, like with my head on my desk like this. And it was like, yeah, threw up a big flop, like going to learn from it benefit of film reviews. And it was just like, you know, and that was just on the spot. Right. Dude, that is the candid stuff that people appreciate because it's not overproduced because it doesn't have this feel of like, I wrote this and then pronounced it really intentionally so that it had this inflection so that you would feel this certain way. Like we are hyper sensitive when we consume content around how it makes us feel. And my content, John's content, Morgan's content is always been super authentic before it's anything else.
Most of the time we might have one or two instances where like we're filming something and holding our phone in front of our face and a big truck goes by and we have to like, okay, let's start that one over because that noise was disturbing, but the way that we say it is going to change when we take that take two. Yep. And we're okay with that. This is where you're headed right now. You got to get to that point. And the way to do it is through consistency and really being okay with your delivery. My advice to you is rehearse it in your brain and say it out loud two or three times, whatever the idea is, shoot for like one, two, three minute bits, right? Whatever that idea is, go for it and consistently like run through it in your brain and then spit it out once, twice, three times, then turn the camera on.
And you're going to find that your ability to like play to your audience becomes so much easier. Yeah. Yeah. And that's what you're after is like the ease in which you can put content out consistently because here's what happens. It's not supposed to take tons of time. It's supposed to be quick and dirty and easy because the real job is this other thing that you get paid to do. Yeah. Yep. And I think that's been, it's a great point. And I think that's been a bit of the hurdle for me is that I've already talked at nauseam about the difference in this job and it's the nature of SaaS. It's metrics driven, right? There's transparency across everything and it's changing. And it's, it's interesting.
Interesting. How so? Well, think about it, right? Would you rather your reps, if you were a leader, would you rather your reps come in and make 150 calls and maybe they schedule two meetings and one of them has like a 50% chance of closing? Or would you rather them come in and spend an hour or two doing research on 50 accounts and then power houring through those accounts and dialing people and having meaningful conversations about their industries and their verticals and scheduling 10 meetings where seven of them have a high likelihood of closing? Which one would you prefer? Well, I know what one resonates with me more. I mean, I, I, I haven't really been an outbound prospector before, right?
You know, I had a, had a stint knocking doors in orange County, California, baby, uh, selling home security, like after my undergrad, right? That was like, by chance, uh, we were just like a subcontractor. Um, I had a friend that did it for ADT. So I was, that's why I was, yeah, same idea, same gig. Um, but I love that because personalization is important to me. I understand you can only go so deep. You've got to stay broader initially, but that is what I enjoy doing is not having a call being like, Hey, uh, James from, uh, you know, blank, blank, blank. I see that you're a VP of sales, right? Yeah. Right. Like that's, that's really hard for me because it goes against like the culture here where I grew up, it goes against the, you know, my, my fabric to a degree.
You have to, you have to also know that that is how 99% of salespeople act. That's what they think their job is. I literally had a conversation with a cold caller yesterday. First of all, let me say upfront, I love cold calls. Like I want your cold call. I might learn something from you if it's a good cold. Yeah. Problem is there are rarely good cold calls. I literally had a cold call yesterday. I answered this is James. How can I help you? That's the way I answer my phone when it's a call that I don't have saved in my number in my phone. Uh, and I, and the lady was, hi, I'm calling to set an appointment with my VP of sales. And I was like, I don't, who are you? Like, I don't know who you are or what you do.
Who are you? Uh, and she was like, my name's Cindy and I'm calling from, and my VP of sales would like to meet. Are you free on Thursday at two? And I was like, I don't, I don't know who you are. And I know this is going to sound crazy. I would love to, uh, have a real conversation about what you do, but like, what do you know about me? And she freaked out. She hung up on me because she didn't know anything about, about us. I called her back and was like, I think we might've got disconnected. And she was like, oh, I'm so sorry about that. I see that you are, uh, sell better sales training. And I could tell that she was like reading it off of my LinkedIn and I was like, this is fine. Listen, I'm not mad at you.
I don't want you to feel like I'm upset or upset or anything. I'm not, but like, please read my, read my stuff. If you still feel like we should talk, let me know. I'm happy to have a conversation with your VP of sales, but I know nothing about you. And you want to schedule a call with your VP of sales to like, sell me something. This is not the way that things work today. You should know that. So like, let's talk about it for real. And she was like, I'll call you back. And she hung up. I never heard back. Uh, yeah. And, and like, this is the way that this is the way that it goes. Like we think a lot of sales reps think that their job is to make as many calls as they can. And literally like almost force people to take meetings for reasons unbeknownst to them.
And buyers are not responsive in a positive way. This way, this is why forecasting has become so complicated. Right. And we could talk about that forever, but like, think about it this way. If I go into a one-on-one and I'm a closing sales rep, I'm coming in and I'm seeing all of these opportunities and I'm like, this one's going to close. This one's going to close. But if I'm the leader, I'm like, what makes you think that one's going to close? And really they're just feelings. Yeah. They're just feelings. I just have a feeling. Yep. And, and depending on the person, sometimes that feeling is a smart feeling. Others that's true. Others it's like, yeah, that's, that's just awesome. Think about it from the AEs perspective.
They're getting, they're getting all these meetings set from a person that's literally just calling going, Hey, when I have a meeting, like they don't even know what they're walking into. It's true. What a 20% show rate if they're lucky. Yeah. Yeah. Yep. So this is why it resonates with me when you say like just the care and the meaningfulness behind it and the humor and the lightheartedness. And, you know, I think SDR, I think salesperson put it in whatever box it might look like for you is shifting to this consultant role quite naturally. Like if you're in sales, you better be ready to have a healthy, meaningful conversation with people about what they do, about what you do and about how that might work together.
And if you can't have that conversation, you shouldn't be making the phone call. Yep. I totally agree. I am a hundred percent aligned on that big time. So tell, tell people that watch this. Uh, and I don't know, honestly, like I was literally handed, Hey, you have to talk to this guy. That's how it came to me. So like tell people that might watch this, uh, how they reach you and why they should. Um, yeah, so, I mean, you can, you can obviously find me on LinkedIn. You can ping me there. Um, check out the proposal five site. Um, would love to just have a conversation business or otherwise, to be quite honest. Um, enjoy the, I really enjoy the process. Get it to know what drives you personally, professionally, what makes you laugh.
I'll tell you a little bit about the East coast where I've waved my tourism flag, get, get you here to Nova Scotia post COVID. Yeah. Get some good seafood into your belly. And, uh, and go from there. Awesome, man. Well, Hey, what can I do for you? How do you want to, how do you want to wrap it up? Anything I should know? Anything that, uh, that you want to throw out there? I think this has just been a lot of fun. I mean, I I've enjoyed, I've, I've learned a ton from you. I knew right out of the gate, we were going to, we were going to get along quite well. I guess I'm curious what this is gonna, what this is going to look like. Like what is, what is this conversation resulting in? Yeah, it's a great question.
I think that, uh, it's probably going to result in some pieces that we share, uh, out to the world. I'd imagine we're going to have several clips that we cut out from this. Uh, that's what I do is I have really healthy and amazing conversations with people. And then I chop all that stuff up and we share it out. Uh, you know, and people love it. It's, uh, these types of conversations are the kinds of conversations that others learn from. Um, and that, you know, I, I always say to people like everybody's made mistakes. The problem is that we think we can't learn from other people's mistakes. We can only learn from our own. That's not true, right? Like if we tell stories and we come out and we tell things about what's working and what's not working and how we got where we are, it helps other people get there too.
And I talk a lot about the fence. There's this fence that I think it exists and only a few people see it. But I ride that fence and that fence has two different types of people on both sides. One side of the fence is full of people that want to be where I am. And I am always reaching down to help them get up on the fence. And then the other side of the fence has a lot of people that are where I want to be. And I'm always reaching up to them so that they can help me get to the next fence. And if I keep riding these fences, I will always be helping other people survive, win, be successful, be happy, find what they're after, achieve their goals. And that kind of is what I like to do. I feel like that's what's given my life purpose.
So I ride that fence very happily. And I teach other people to ride the fence as well. I love that. That is an excellent analogy. I've never heard that before. That's a beautiful thing, my man. No, I mean, other than that, I'm not sure how you can help me, James. This has been a lot of fun. Well, I'm going to be sending people your way. Every time I have problems with proposals with people and they say, what should I do? I'm going to be like, this is the guy for you. Talk to them. Yeah, I mean, business-wise, that's the obvious one, right? But I guess I'm curious. You know, you said talk to this guy. Like, is it what you expected? Is it? Totally. Yeah. No, everything they said about you is true.
Yeah. You've smiled the entire time through this whole thing. It's genuine. I mean, it's not a Zoom mask. It's a way out. I like that. The Zoom mask. That's good. That's an article right there. That's a piece of content. Although, piece of funny content that I actually, I've almost reached out to get permission to share it. So this door over here, which funny enough, looked just like your opening not long ago. It didn't have trim or painted casing for like, I finally got around to doing this. I'm a DIYer. So it was just like unfinished doorway. And I'm partway through a demo with a client. And it's going good. They're pretty engaged. They weren't really engaged on the disco. So like, I was getting some good back and forth.
And all of a sudden, I see the guy kind of looking like you're looking right now, looking behind me. And I see my videos up in the corner so I can see behind me. And I look and it's my little guy, Ivan. He's like, it'll be four in January. And he's in a full Spider-Man costume. And he opens up and walks in and just like, dad, dad, dad, dad. And the day before, I literally had, she was, it doesn't matter her title, but she was overseeing marketing and sales at a particular organization. And her, her little, like two and a half year old came in and she's like, I'm so sorry. Grabbed him off the bed behind her and like shuffled him off. And I was like, it's all good. This made my day. So Ivan comes in, gives me a couple of pokes and he's like, mom, got you a, mom, got you a new Batman costume and they're losing it on the demo.
Like the two folks on the, my demo are like having a time laughing at him. And, uh, anyway, looking back at the video, you see the door for almost like 40 seconds, like open a little further back, open a little further. He was just like trying to get the guts to come in. Is he, is he, is he, is he anyway, he came in and I just think it's like, moments like that, that are just so special to like relate. Like we're humans, right? We have day to days, like, you know, stuff like that is what changes the way that we interact with each other forever, man. Like nobody is going to condemn you for having your kid in the room on a call. And there was a time in our history when that was unheard of and not acceptable.
So I love where we're headed as a community of people that understand that we're all human beings. And I think if we can really dial that in and accept that from one another, then we'll find much, much better conversations are for us in the near future. Mm-hmm. Yeah. Absolutely. Absolutely. Listen, I didn't really share a good dad joke with you today. They're all, you, you put me on the spot. They're all my job to put you on the spot, Scott. But you know what? Half the humor that comes out of my mouth is, uh, actually no, 90% of the humor that comes out of my mouth is, is on the spot and just kind of some sort of saying I pulled out of thin air, but it's, uh, it's a lot of fun chatting with you, James.
Well, keep me posted. Let's do this again sometime. Don't hesitate to reach out if I can help. And I appreciate you. I'll end this one the way that I end most of my content. Hashtag say what sales, if you're a salesperson, we're the same person. This episode was so uplifting. I know that there are a ton of professionals out there that got some inspiration from what Scott has brought to the table here today. Special thanks to our partner Proposify for suggesting that we connect with Scott to hear about his mentality and mindset. And don't forget that you can subscribe at ondemand.jbarrows.com. We look forward to continuing to deliver the skills needed to be the best sales professional possible as you navigate this career that we call a sales life.
Reach out to me anytime at james at jbarrows.com and we'll see you next time. Make it happen.
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