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Build A Selling Skillset – Joel Stevenson

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Joel Stevenson is the CEO of Yesware, a company that builds software that helps professionals communicate efficiently and authentically by integrating a powerful set of tools right inside your email inbox.

Some of Joel’s accomplishments have been building a supply chain business from $2MM to $30MM, a B2C eCommerce business from $50MM to $100MM and a B2B business from scratch to several hundred million.

 

In Today’s episode, Joel talks about his start in sales and how his background in acting has helped him think on his feet from time to time. But, most importantly he discusses how he’s been shaped as a sales leader to be curious and focused in order to accomplish his goals.

 

Tune in to Joel Stevenson’s episode to learn why you might be cut out for sales and why at the end of the day everyone should know the tricks of selling in order to further their career.

 

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Transcript:

Thu, Dec 23, 2021

SUMMARY KEYWORDS 
sales , people , crm , salespeople , person , selling , big , role , company , questions , quantitative , revenue , rep , career , business , sales manager , buy , area , success , individual contributor

SPEAKERS
Joel Stevenson & Christopher Smith

Intro
Welcome to the Sales Lead Dog podcast hosted by CRM technology and sales process expert Christopher Smith, talking with sales leaders that have separated themselves from the rest of the pack. Listen to find out how the best of the best achieve success with their team and CRM technology. And remember, unless you are the lead dog, the view never changes.

Christopher Smith
Welcome to Sales Lead Dog today I have joining me Joel Stevenson of Yesware. Joel, welcome to Sales Lead Dog.

Joel Stevenson
Great to be here. Thank you.

Christopher Smith
You bet. It’s good to have you on Joe. So, Joe, tell me about your current role in Yesware.

Joel Stevenson
Yeah, I am the CEO of Yesware. I’m actually not the founder of Yesware. I joined the company a little a little over four years ago. And Yesware is a sales productivity tool. So, we are built for salespeople and sales managers, we integrate deeply into the inbox, and we save you time by automating manual activities that you’d have to do yourself and also provide intelligence and information that you can then use to be more productive and more effective as a seller.

Christopher Smith
That’s such a needed tool to be effective as a salesperson these days using any kind of platform of engagement. But if you’re not engaging effectively over email, it’s a struggle.

Joel Stevenson
Especially now with pandemic situation, everyone’s remote seller, whether they like it or not.

Christopher Smith
Yeah, have you guys embrace that? In terms of, you know, your strategy with Yesware?

Joel Stevenson
Yeah, well, we, I suppose we have never had a bigger opportunity as yes, we’re as a result of these changes. Because if you think about, you know, I think probably the last study I saw this was maybe four or five years ago, there was a view that there were 6 million non-retail sellers in the US. And under 6 million, about half of those were largely in person and about the other half was largely remote, a little, you know, give or take. And I think now, it’s probably, you know, 99% are mostly remote in probably, it’ll go back, you know, towards his things, you know, hopefully normalize more and more people doing things in person again, but I don’t think it’ll ever go back to the way it was. And so, you know, if you think about being a remote seller, for a lot of people, the hub of your workflow is going to be in your inbox. And so, you’re going to naturally spend a lot of time there. And so, by yes, we’re being deeply integrated in your inbox, we’re sort of integrated into the hub of your workflow with the outside world. And so, we’re, we’re just seeing more and more engagement with the platform and more and more opportunities to start to make, yes, where they are being a part of people’s selling lotions.

Christopher Smith
No, that’s awesome. I’m so excited to have you on the show. Because it is a struggle for so many companies to provide a platform or a tool for their sales team to really be effective at engaging over email, you know, it can be a struggle, if you don’t have a tool, I guess we’re so

Joel Stevenson
That yeah, that’s right. I think there’s, you know, there’s been, I mean, you know, going all the way back to the earliest days of sales technology, a lot of sales technology that’s bought, not used. So, one of the things that we really try to strike a balance on his complexity, but not too much complexity so that the learning curve is too high and just meet us and we’re also a freemium product. So, we have a free tier of Yesware. So, he only showed us what our costs are using it. So, there’s, we’ve got to work in a little bit of a more user-friendly way, then kind of some of the more traditional top down, you know, heavy pieces of software. Yeah,

Christopher Smith
That’s great. So, thinking back over your whole career, Joel, what are the three things that have really driven and led to your success?

Joel Stevenson
Yeah, the luck maybe the biggest one, but I suppose that that’s probably not that helpful, but for your purposes, but yeah, is I look back there’s a few things I think probably number one, because you know, because sort of starting in, in a cell integrity, communication skills, is probably the thing that’s helped me the most, and I was, I did had some acting in my background. And you know, I’ve sort of always been in front of people in audiences and so I always was able to sort of fall back on that even when maybe I wasn’t as prepared as I should have entered in understand, maybe the level of hard work and preparation that was required at Intel, we succeed in success in things like sales, so that was helpful. And then something I picked up a little bit later in my career was sitting meditation that’s really been helpful to me in terms of focus. And you know, really just being more intentional and more present with the things that I’m doing I’m, I would say like, I’m really just starting to really reap the benefits of that now in my 40s. And then the other thing was maybe a bit of a career transition that I had, which is I’d started in selling, and, you know, mostly was sort of out in front of, you know, various customer facing roles. And then, when I did my MBA, I had more of a quantitative focus there and finance. And then I worked for a very quantitative consulting firm, right out of that. And so, then I was sort of add, able to add sort of the, you know, externally facing skills with sort of the more internally facing analytical skills, and then that sort of helped me sort of move into bigger management positions over time.

Christopher Smith
That’s very interesting. He answers, you answered your question very differently from people I’ve had on the show in the past. You started off by saying luck. Do you believe people create their own luck?

Joel Stevenson
Well, what’s it the thing? You know, luck is when preparation meets opportunity or something like that? Yeah, I believe that’s true. To some extent. I mean, certainly, there’s, there are opportunities that are presented to people that they miss out on because either didn’t prepare enough, or they didn’t work hard enough for you maybe in some sense, they just didn’t have some of the fundamental capabilities that were required to take advantage of that situation. So, I think that is true. But then there’s also this, this notion that like the difference between like success, and wild success is often what because you know, to be somebody that’s, you know, very successful over long period of time, like, you probably have a lot of the same skill sets of the person that has been wildly successful over time. And maybe, you know, that person canebrake that you didn’t, I think is part of it. And then, you know, another aspect is, you know, I grew up in a middle-class neighborhood, and either way, I’m first-generation college, but the relative to others, I had an awful lot of advantages to sort of growing up and going to school and going to college, and then joining a company with good training. And so, there were a bunch of things that were sort of structural to the system, that I just, you know, benefited by just being born who I was when I was,

Christopher Smith
Right, right. No, I grew up with that completely. I mean, it’s let’s, I don’t think about those advantages were given. Because we still may be struggling. But in reality, we’re still we’re struggling, but we’re struggling ahead of other people that didn’t have those same advantages. So that’s right. Tell me how did you get your starting sales?

Joel Stevenson
Yeah, I, um, well, it’s, it’s a little bit of I remember that we had I went to University of Illinois for my undergrad, I remember we had this this guy, Layton uni, who was the founder of X software,

Christopher Smith
I don’t know if he told me.

Joel Stevenson
And I remember him saying something about, you know, he’s just like, a, like, how many of you, you know, are in sales or planning go into sales or something like nobody raised their hand, and he’s like, well, I got news for you, like, you’re all going into sales, whether you like it or not. And, you know, if you want to, you know, if you want to build a skill set that’s going to be useful for your whole career, like you might, you might think about, you know, building a selling skill set. And I had done a little bit with it. With another guy that I knew was sort of a part time job in college. And then I ended up applying for a whole variety of different jobs. And the job that ended up getting there was seem the most interesting at the time was with this company, and now doesn’t even exist called ZTE, which was one of the big regional telephone companies. You know, that was one of the non-AT&T. This sort of at all of the none, you could argue the non-desirable areas in the country, but then it’s an issue, but they were sort of known for having a really good training program and investing a lot in their in their folks. And so that was going to be an opportunity. Like, I don’t know what I’m gonna do in long term, but I want to start in selling I want to have a good foundation in selling and so that program was not six months, before you actually took it first territory, which, you know, when I think about how we, you know, I bought on boarded salespeople in northeast part of Italy, that it was a real luxury and they didn’t even appreciate the time so that’s it I just thought it was sort of a good place to start and I would see where things you know, went from there.

Christopher Smith
Six months is insane. I don’t know of anyone who’s doing a six-month trailing training program now.

Joel Stevenson
Yeah, yeah, I mean, it was and there were some aspects of it. I think it’s retrospective maybe couldn’t pull off now where we spent a month at twice at this GT had bought the old Braniff air for air airline headquarters on the doubt DFW airport grounds. And this was a long time ago like it was in the area in between Fort Worth and Dallas like wasn’t really that exciting. And so, you know, you got Maybe you were 20 of us, you know, right out of college and you thrown into this hotel with, you know, with a month with each other and a bunch salespeople. Yeah, there. There were Yeah, it may be hard, maybe it could be a reality TV show. It, that was a that was sort of I don’t know if you can do that, that but we were there for a month. And then we went away back to the branches. And then you had this whole giant checklist of things, you had all these ride alongs. And we’re completing trainings and technical information, we’re selling reasonably technical things. And then you went back for another month at the end to sort of finish off your education and sort of, you know, get certified, if you will, and then you were then you were thrown into whatever territory you were thrown into. But yeah, it was incredible to be able to watch. You know, I don’t know, 100, or more in person sales calls before ever having to do my first one myself.

Christopher Smith
Oh, yeah, took about a learning experience. But it won’t get any better than that, you know, just to be able to be able to fly on the wall. Do you have any key takeaways from that period, things that really set a foundation for you moving forward?

Joel Stevenson
Well, I do remember, in one of the first ride alongs I was ever on it was we went to an insurance agency. And the guy who was running the agency was the one who was making the telecom decisions. And so, you know, I mean, insurance agencies are sort of known for also having like, pretty structured set of sales trainings and philosophies and that sort of thing. I remember that. First, he’s like, oh, are you new guys, you know, the first thing he said was the only here’s, here’s what you got to know about sales, God gave you two years, he gave you two years in one mouth for a reason. Don’t ever forget that. And, you know, and I think that was that that is, you know, like a very simplistic thing that this stuck with me along with, you know, you know, how would you then use that? Well, you know, how you use your mouth is, you know, we had a lot of the sort of the, you know, professional selling skills and the Miller Heiman stuff and reviewing, selling and tactical selling and all that, and, you know, eventually later got into SPIN Selling, but a lot of it is really the, it’s really the questions that you’re asking people, you know, is so important. And so, as I’ve, you know, developed in my sales career, and as I’ve tried to bring new people on, I’ve always tried to focus on making sure that, you know, whatever sales team I’m responsible for, we ask questions, and we understand the customer’s business.

Christopher Smith
I, that is actually on my list of questions I ask. You know, my guess is, how do you teach someone to ask those good questions?

Joel Stevenson
Yeah, well, some of it. I suppose there’s, there’s a portion of it that has to do with how you’re wired as a person. And, you know, we use a selling methodology here. Yes, we’re called selling through curiosity. Very wine put together years ago. And, and that’s part of it, I think, is like that, like that name sort of captures some of the zeitgeist of it, which is you have to be a curious person, I think, you know, in order to want to ask the right types of questions, because it’s easy to say like, you know, sort of simple, yes, no types of questions that can get you into some trouble over time. But if you’re, if you’re really curious, like, you want to know how this business works, and you want to know, Can I really help this person, make a better business outcome? Like, can I get this person promoted, like, like, in without, like, really asking us a series of interesting questions. It’s hard to get to that. So I think it sort of starts with, you know, does the person have the interest and the aptitude in doing that sort of as a first point, and then, you know, the second thing is, you know, what can you do, as part of your training and onboarding, to help your reps understand the customer’s challenges and there, the, the business context under which they’re operating so that they really know. And so, I think, you know, a good a good structure training program of like, the core selling skills, but then also with, adapted to, or modified with whatever business your industry you’re tending to sell into, and it can be useful.

Christopher Smith
What role does empathy play in formulating those questions?

Joel Stevenson
Yeah, I think, I think a big role in the sense that the better a rep can do at putting him or herself in the customers shoes, the more likely you are to ask a good question. Whether that’s about you know, how does your business work or how the selling process works? Or, you know, trying to understand if, if you fully answered the, the prospects questions are trying to read body language to know maybe when you’re pushing too hard, or maybe when you’re sort of, they’re starting to lose the person from an interest standpoint, like getting off All of those, all of those things that may be separated like so. So, salespeople from really good salespeople, and empathy is a big of a common factor and all those things,

Christopher Smith
Right? If you could take one piece of knowledge you have today, and go back in time and give that to the young version of Joel just getting started in sales, what would that be?

Joel Stevenson
A discipline in the process. So, I think there’s a, there’s a set of skills you have to develop, but then at some point, you have to have a plan and work your plan, you know, not only for an individual deal, but for an entire territory. And, you know, you have to, you have to know that to get a sample, yes, you’ve got to endure 100 nose or whatever, however many ends up being and just understanding that without me without sort of making sure that you’re putting in the effort to get the top of the funnel results, and then continuing to work all of those deals, then turn into something and not being discouraged by all the nose, but knowing that the nose will lead you ultimately to a yes, if you’re disciplined doing the right sets of things. I think that’s, that’s a key one I get early in my sales career, I would get discouraged by the losses, and then that would make me more tentative than trying to then you know, sort of sell to the next person. And that’s really tough for really tough for a salesperson to be successful.

Christopher Smith
Oh, you know, I believe it. Tell me about your transition into sales leadership. What was behind your decision to pursue that path? Yeah, well, some of that was

Joel Stevenson
Something that was intentional. And some of it was sort of non-intentional in the sense that before my MBA, I had done admin, a rep, I had been a sales ops person, I had done Channel Sales, I did some alliance management, sort of a whole mishmash of things, but all effectively individual contributor type roles. Then when, after MBA, I worked for a company called Zs associates, which is a very sort of quantitative sales and marketing consulting firm, they sort of made their name in the farming industry in the early days and was started by a couple of Northwestern professors that doesn’t really shake computer modeling around like the traveling salesperson problem, which was a real thing in pharma back then. And so, in that job, I was able to work with sales leaders, from a variety of different industries and companies about some of the challenges that they had about their Salesforce size, or the Salesforce structure, what they’re asking the reps to do, or trying to balance, compensation versus opportunity. And so, I started to get exposure to more and more of those types of questions. And then were happening was one of my MBA classmates join a startup company in Chicago. And this is when I was at Zs. And at some point, in consulting, you have to make a decision about like, I’m going to be a career consultant, and try to pursue the partner path or like, I’m going to go do something else, because the lifestyle in and of itself, particularly back then, can be a demanding lifestyle in terms of travel and work hours, and all those things. It’s like, it’s sort of like if you’re not really willing to go and go to the end, it’s sometimes can be difficult to sustain that for long periods of activity and family time. So anyway, I decided to join the startup company just sort of caught the bug because I had a lot of success around my career tech companies at icon so we’ll go do this company. And in that company, I was more of a, I guess we’ll call today like an account manager or like or customer success, where we had these big programs have been on boarded with folks, we know revenue, we had to try to get to a place where they were generating 10s of millions of dollars of, of revenue. And so, I had started to figure that out. And then eventually, I was able to build a team as part of that. And then I did another complete 180, which was I went to Wayfarer all the time with CSN stores was named Wayfair. And ended up managing basically being a general manager, a bunch of websites, that for a period of naps were the sort of the next sales manager things sort of happen by almost by accident.

Christopher Smith
So, before the show, I asked you if you had like a crazier, interesting story from your career, and you shared a little bit about wafer. Can you share that with our audience?

Joel Stevenson
Yeah, so this may be one of those a little bit of like, you know, preparation meets opportunity that we were talking about earlier. So I was managing 20 or 30 websites that had to do with renovation and home improvement and we back that was before we had wayfair.com. So, we had at our peak five or six 100 microsites, like all the way down to like all rooster decor calm, I think was the most ridiculous one. But I had ones like, every vessel sank, and you know, like concrete equipment kind of it was it was a over it was all variety of different things that we were doing there. And what we did a lot of business in lighting, we did a lot of business in, in plumbing fixtures. And as you started to look at who was buying, you would eventually start to see, you know, 100 orders that was, you know, a single light, and then someone would show up and buy 50 lights and like, Oh, that’s funny why that person buy 50 Or you would see people and they buy, you know, 10 a month type of thing, oh, who are these people were doing. And you know, they’re, as you would expect, they’re electricians, they’re contractors, they’re interior designers that are buying behalf of somebody else. And so, I was able to convince my boss to sort of, you know, secretly give me a couple of customer service people so that we could call into these folks. And the guess was that if we just treated them nicely, and gave them really good service, and we could increase the amount that they were buying from CSN stores at the time now Wayfair. And so we that was hypothesis. And so, we need spend some time, like we blocked off, you know, a few days. And we were just banging the phones, I you know, we all three of us were calling her I was helping them on their calls. And it was just a complete bust. We people did not really want to hear from us. And you know, it was it was pretty discouraging, honestly, but there was something there. Like, there were a couple of conversations, I was like, there’s there really is something to this. And so, after a bunch more of those calls, we were able to get a few people to say, Okay, fine, I’ll call you, like I want to do and I said, Sure, what could it hurt, like, you know, be at my beck and call and we were we were absolutely at their beck and call. And so, we were then able to prove that, you know, hey, we’re certainly get a little bit more revenue out of these folks. And then actually, there was this was an ongoing argument for years about whether we were really driving incremental revenue, or whether it just sort of taking money out of one pocket and putting it into another, but eventually be proved, I believe the shadow of doubt that this was an incremental program. And then we basically said, Alright, we’re doing this. And so recently, we added a bunch more reps, we started adding a management tier, it grew, and it grew, and it grew. And then I actually went to run our, our UK division for a couple years, and then that this thing just sort of went and started to grow and grow and grow, I came back and it was actually the finance roll away for a while. And this little, you know, sort of random side project all the sudden was $100 million division of Yesware. But it’s sort of gotten a little bit disjointed across the various vert divisions. And so we decided, well, let’s, let’s consolidate it. And let’s, you know, put a general manager in charge of that, let’s try to see what we wrote. And so, he took it back over again, at that point, and we you know, we grew it from you know, we had 100 People at that point, and we grew it up to you know, like 500 people and almost half a billion in revenue. That’s amazing. And nowadays there was an article in Architectural Digest my this woman Margaret Laurence took it over from He’s done a great job now it’s a billion and a half.

Christopher Smith
Yeah, that’s amazing. That’s an incredible story. Thank you for sharing that’s unreal. What was the toughest part about your transition from salesperson to sales leader?

Joel Stevenson
Well, you know that there’s um you know, the old the old joke about the about the sales guys that go on a hunting trip it’ll do a favor that or I’ll try to tell it to saintly but there’s there was a group of guys used to go on this annual hunting trip and every year they go to this this fancy Lodge and in Canada and they would provide the guns and the dogs and the whole thing and so they gone the first year they go they’re like oh I got you I got a great dog for you his name salesman like he is aggressive and he goes out there and no you’ll get you’ll get all the all the file back really don’t worry about easy awesome so they go out and have a great time like a salesman is like on top of a spring it all is bringing all the birds back he’s great. They go back again same experience and then the third year they go back they’re like okay, like we’re salesmen in the manager is how you know Yeah, salesman is isn’t available anymore. Why? What happened? Well, like he did such a good job we changed his name to sales manager and now all he does is sit around and bark all day.

Christopher Smith
I haven’t heard that. That’s pretty funny.

Joel Stevenson
Yeah, I think that’s pretty back in sales or but I think it’s actually not that different from it wasn’t You’re like just a manager in sort of any role like that the sale that salesperson versus sales manager, I think is not that different in the sense that when you’re an individual contributor, you can sort of wheel yourself to success in many cases. But when you’re a manager, the, you know, if you think about the average ratio of coverage ratio of a manager might be one to 718. And they feel a lot of sales team center run a little bit, you know, even more aggressively than that, maybe one to 12, or what a 15. You see in some, in some cases, and so if you think about like your contribution, it becomes very, very hard to will, the whole team to success in that environment, like your success is really going to be a function of what the people on your team produce. And so, you have to then you have a mindset shift away from, from I’m going to do this myself to like, how am I going to help everybody else get this done, and get better and better and better? I think, for me, it might be particularly hard for salespeople, because it’s such an individual contributor, high visibility, high metrics, you know, to make that transition versus maybe some other roles. But I think fundamentally, the transition is the same that you have to make. And so, it’s like, it’s really, can you become a facilitator of people versus a executer of individual plans and conversations.

Christopher Smith
When you join, yes, where you were in charge of sales and marketing. Tell me about your first 90 days in that role. What was your focus over those first months in your role at Yesware?

Joel Stevenson
Yeah, what really, we were trying to diagnose what was going on with, with the sales or sales and marketing organizations, largely, the company was not at that time achieving the results that they wanted, or that the investors thought the company was, was able to achieve. And so a lot of it was really digging into well, like, why are we not achieving those results, like going out and talking to customers, talking to getting on sales calls, talking to the reps talking to individuals talking to other people in the market to kind of get their point of view, but really, the first 90 days was mostly about trying to understand the current situation and what, what was working and what wasn’t working.

Christopher Smith
Is there a do you use that strategy? When whenever you come into a new role, or was this different experience for you?

Joel Stevenson
Um, I try to I mean, I think there’s one thing I try to do when I enter into a new role, and I can’t remember where I first heard this from it might have been from Carlos go. And it was the old Nissan CEO, who was sort of in the news a couple of years back about the whole extradition thing and all that stuff. But I’d seen him speak. He came to, he came to Yale one year in sort of gave a talk about, you know, some of his experiences in life, because he was like the turnaround guy. And so, he talked a lot about that experience. Sorry, I can do that. And it was one of the things I tried to do when I go into a new situation is I try to meet with as many people as I can. And you try to you try to ask me a couple of questions can be pretty interesting. One is like, what do you hope that I’ll do in this role, but then also asking the opposite question, which is, what are you afraid that I might do? And those usually, if they come from a place of sincerity, you can kind of get people talking? And then you know, there’s other questions that depending on the situation, they might want to ask everybody in a more pointed way, but I find that asking those two questions of people, at least internally often produces enough that you can start to hunt down some hypotheses.

Christopher Smith
Right? Right. That’s tremendous. You have both sales and marketing. I know for a lot of sales leaders, it’s very tempting to take on additional roles like hey, I want to own marketing as well. What advice do you have for those people that are considering want to pull in marketing and take on more of a role in that area?

Joel Stevenson
Yeah, well, I mean, I tend to be a fan of somebody on the revenue side owning both of those functions only because they’re so intertwined. And when you when you have a split there, you often end up I think Miss allocating resources across company and like the most obvious example of that is when you get, say, like a heavy outbound function like an SDR BDR team, which effectively is a marketing channel. But may it or may not be working as well as other marketing channels that are working, but it’s like the sales team refuses to let go of it because they’re the Don’t trust a marketing team and then deliver other leads. And so you end up in this position where there’s probably a better overall mix for the company, but because of these artificial boundaries, you know, and then, you know, now with sort of the rise of robots, and you know, more and more systems like that, marketing and sales have, you know, need to work, they’ve always seemed to work well together, like, but it’s never been more important now with, you know, larger digital experiences and people showing up into the funnel being better educated than they ever were. And so I think that’s a, that’s a good thing to try to pursue, particularly as your, as you wanted it to take more and more responsibility for revenue in an organization, the thing that people need to maybe that are coming from the sales side, really need to be attuned to is that modern marketing is extremely quantitative. And if you are not analytical and quantitative, it’s going to be hard, I think, to do that job successfully. You know, it’s like the old days, where it’s in May we, in some ways, maybe, maybe we’re going back to this, so that third party cookie stuff, but, you know, it’s like the old adage about like, well, you know, half of my advertising budget is wasted, I don’t know which half, it’s not so much true anymore. There’s a tremendous amount of data that that is now flowing in. And you can see that the folks that really do a good job with this can accelerate their revenue much, much more quickly than the ones that don’t. And so, while, you know, you maybe don’t have to be so good that you’re actually executing these things like you minimally, you have to be able to recognize exceptional analytical and execution talent in that area. And I think it’s hard if you’re, if you don’t have some, at least, you know, base level of quantitative skill and interest in that area, I think you’re sort of going to be hard to be successful in that. So that’s something that if you don’t have it, now, you got to figure out ways to try to get that, you know, as part of your career. I mean, the other thing that you see in some sales orgs is you’ve got to and I think it’s it tends to the maybe sometimes more of the big enterprise ones, where it’s like the hierarchy is, the bigger the deal is, the higher the person is that sort of takes it is in a more of an SMB motion, that it’s just it’s very parallelize, you know, get sales people, you know, sales leaders parachuting in on deals so much. And so, I think in some of the bigger, more enterprise II types of functions, you end up with people that lead that way, because they end up being the best salespeople, they never fully relinquish the selling side of it. But what ends up happening then is that you sort of outsource everything quantitative, the sales ops, and that that is one way to like, it can work well that way, or you got a very strong, operationally minded quantity of sales ops person paired with a really strong revenue person, that can work. But then when the when the sales leader then wants to go run the marketing department in that same way, I just don’t it just doesn’t work as well. My sense?

Christopher Smith
Yeah, I think, yeah, they are. They’re fundamentally different in many ways, but they have to be fully aligned and connected. And I think that’s the struggle. I think people maybe underestimate, at least that’s what I see in my world.

Joel Stevenson
Yeah, right. And it’s way better when they are. So, if you can get a leader that understands both parts of or can learn both parts of it, I think, is an organization you’re going to end up achieving better results. But some, you know, it’s these are, you know, tough, they’re sort of diametrically opposed in many ways. And he’s what people will leave about the fundamentals of them. And so, it’s hard to find the people that can kind of cross both sides. Oh, totally.

Christopher Smith
Let’s talk serum for a minute. When it comes to CRM, I think I know your answer. Do you love it or hate it?

Joel Stevenson
Um, yeah, you know, I guess at the moment I see it as sort of a necessary evil you know, in part of the yes, we’re value proposition is that we’re sort of taking your email activity and passively syncing it into the CRM. I think it is we look you know, I mean, for as long as systems like CRM have been around there have been issues with adoption. And you know, if you think I think back to you know, doing an Orem instill in, you know, CRM installation as part of a task force in my first job, and how things really like, in some ways, haven’t changed that much over time. And, you know, I think of all of the all the major CRM systems as being they were designed in person, first world, and they were also you know, a lot of the fundamental design principles of CRM came from a time when not everybody had an email address. Not every company had a website. And so, like the ways that you identify people and like all the data in sort of challenges that come up over time, I think, you know, many of these things are artifacts of the of the fact that you had these things. They were designed for a simpler world that are now trying to adapt to a more and more and more complicated world. It’s now a remote digital first world. And so, in my view, there’s, there are systems opportunities to build something that has, you know, accomplishes some of the same goals a CRM is traditionally accomplished, but do it in a, in a world that recognizes that it’s a digital first remote selling first world versus an in person first world.

Christopher Smith
I love that answer. It’s you know, when I see such a need for tools like Yesware, because the court the, you know, the big players out there just don’t, they don’t make it easy. For the salesperson they didn’t, or they’re not really enabling the salesperson, they’re tracking the salesperson. And to me, it should be all about enabling, I want to make their job easier. I want to make them more efficient. I want to motivate them. I want them to look at us as like, hey, this is a tool that’s gonna make me more money. Bottom line, and so many fall on their face in that regard.

Joel Stevenson
Yeah, man, like, how many times have you heard Oh, are the data in our CRM is a mess?

Christopher Smith
Oh, yeah. All the time. That’s usually one of the first parts of the conversation I have with people, is we’ve got crap data, and usually use another word. And it’s just, to me, that’s a symptom of the overall disease, you know, and in, so it’s unfortunate. It’s why I started my business is that I just drives me crazy that CRM has done so poorly, and so many companies. Yeah, yeah. What it doesn’t have to be, you know, there are great tools out there, like guess where and other tools, you know, that can really just make it easier for your team to do what they need to be doing.

Joel Stevenson
Yeah, that’s right. Yeah. I mean, I think that you know, the other the other thing that I mean, sets, the founding principle of Yesware, when Matthew and Cashman originally went out and raise money for it was this idea that like, we’re building software for salespeople, and when they heard from a lot of the investment community was like, There’s no such thing as that. Their CRM, but CRM still for managers is not built for salespeople. And if you think about, you know, like, the all the Ruby selling processes that I was part of years and years ago was like, well, like, you know, looks like your rep is going to walk out the door with a Rolodex of people and all the information. And then what are you going to do with that? I feel like that was the main selling proposition for CRM in the early days along with, you know, pipeline management, and some of that stuff. But, you know, it’s like, now that isn’t really a problem, because you have all the data because you have old emails, and you have, you know, Slack conversations or whatever else it ends up being. And but you, but the legacy of like the tool is for control, versus the tool is to help the rep produce a better result has never fully been resolved. I mean, I think a lot of major vendors make good strides in this area. But there’s a design parameter that I think was missed early on.

Christopher Smith
Yeah, I agree. I agree. Well, Joel, I really appreciate you coming on Sales Lead Dog, if people want to reach out, connect with you if they want to learn more about Yes, where what’s the best way for them to do that?

Joel Stevenson
Yeah. Yes, we’re calm is a great place to start. We’ve got a blog that you can find from yesterday.com. We got hundreds and hundreds of articles from about sales productivity, and it’ll be a better seller, and somebody points at work. And if you if you want to try Yes, where we’ve got a free tier, you can use it free forever, either Outlook or Gmail. Yeah. If you want to be in touch with me, you can just email me Jay Stephenson at yes, we’re calm.

Christopher Smith
Yeah, we’ll have that all on our cold call notes. If you missed that. And I will I want to compliment you on your learning content on your site. I’m really impressed with that. I think that’s another area where companies found their faces. They’re not really supporting their customer base with meaningful learning content. You guys do a great job.

Joel Stevenson
And we appreciate that. Yeah, we’ve got a great team that works hard on developing content and it’s affordable.

Christopher Smith
Yeah, that’s awesome. Well, again, thanks for coming on Sales Lead Dog.

Joel Stevenson
Yeah, thanks for having us right.

Outro
As we end this discussion on Sales Lead Dog, be sure to subscribe to catch all our episodes on social media. Follow us on LinkedIn, Facebook, and Instagram. Watch the videos on YouTube and you can also find our episodes on our website at empellercrm.com/salesleaddog. Sales Lead Dog is supported by Empellor CRM, delivering objectively better CRM for business guaranteed.

 

Quotes

  • “The hub of your workflow is going to be in your inbox. We’re being deeply integrated into your inbox.” (2:25-2:32)
  • “Something I picked up a little bit later in my career was sitting meditation that’s really been helpful to me in terms of focus.” (4:38-4:46)
  • Well, I got news for you, you’re all going into sales, whether you like it or not. If you want to build a skill set that’s going to be useful for your whole career, you might think about building a selling skill set.” (7:58-8:01)
  • “You have to be a curious person, in order to want to ask the right types of questions.” (13:10-13:15)

Links

Joel Stevenson LinkedIn
Yesware LinkedIn
Yesware Website

Empellor CRM LinkedIn
Empellor CRM Website
Empellor CRM Twitter

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