HOW ANYONE CAN LEARN TO CRUSH IT IN B2B ENTERPRISE SALES

What if you're not a born salesperson?

What if you're pretty much the opposite of a born salesperson?

Somebody who people never thought would get into sales, had no business being in sales, had no personality for it.

Oh, but can we change?

Can we grow? Can we develop? Can we become somebody that we want to be, not just who we are today? That's the topic today. And boy, do we have a great guest for you. And a great interview. We got somebody different doing the interview today, but somebody you may know also. Let's get into the interview. I think you're going to enjoy this, especially if you're not a natural-born salesperson. And you might say, well, uh, well, this person sounds like they are, but maybe they grew into it like you and I are, that we're a little, uh, pollywogs turning into big bullfrogs out there. Caterpillars turning into butterflies.

That's the topic of today.

Let's get into the interview and I'll sum it up at the end. If you're in the courses, have you checked out the app? Oh, it works amazing. Go log in and in the community I give you all the instructions on how to get it.

Here we go.

So first-time interviewer, longtime listener. I know, Brian, you're always interviewing a lot of the top sales reps across the country, and we appreciate that. But I think a lot of folks would like to kind of hear a little bit more about your story. So we're gonna flip the script today, and I might steal some of your questions too. But starting off, I guess, just tell us a little bit more about yourself and a little bit about your story and background.

Well, I'm a podcast hoster. No, I mean, my origin story is, you know, I was raised by 2 salespeople, you know, did the sales jobs in high school and a couple during and after college. But I was really a software developer first because I saw at the time in Boston where I grew up, You know, the want ads were about 30 pages of software engineers and 1 page of everything else. So it was very clear to me growing up that there was infinite demand. And although I wasn't naturally talented at it, you know, I just went out and bought a Radio Shack color computer and taught myself how to program. How to type and then how to program. And I loved it. I enjoyed it. You were building something, but I kind of quickly realized that I was at best a B-level engineer. And I didn't have the intellectual horsepower, nor— I did kind of have the 80-hour dedication, but I knew it was going to take about 160 hours a week to get to where I wanted. And there aren't that many hours in the week. And then I found out what salespeople made. I was out to dinner after doing a sales call. I was the engineer helping out this lady and her base was higher than my target income. And I was like, yeah. Wow. So there was no downside. And then she happened to tell me that she was gonna go to chiropractic school. Which made it known to me that she was leaving her job. And I said, well, do you mind if I ask for your job after you give notice? And she goes, I don't care, just don't do it before I give notice. Gotcha. So she left, I took that job, and it's been sales ever since.

That's an awesome story. So what were some of those initial Kind of roadblocks or epiphanies when you made that transition? Did anything stand out of how sales was completely different from engineering or what were the good things and bad things?

Well, I went from being treated like a god to being treated like a dog. I used to ride my bike into work, came and went as I wished. I was building the product. I was the chief guy on it. And the product was taking off and it was in the press. Everyone loved this. The engineering VP was like, why do you want to be a sales rep? And I'm like, I'm kind of money motivated. I built this product. It's a hit. I didn't get a bonus. I didn't get a penny. I didn't get a share of stock. So the writing was on the wall that engineers are valued but rewarded with lifestyle, not with economics. In sales, there's no lifestyle rewards. I had to cut my ponytail, get a car and drive to work and be there before 9 and stay well after 5. And it was, we had quite a bit of inbound, which was good, but it was a hypercompetitive space and it was a tough A tough road there.

Well, I think you should bring the ponytail back. That's a side comment, but that would be a good one. And then as you kind of progress in your career, you worked at some smaller companies and startups and I think a little bit the bigger companies. What did you like and dislike about some of those smaller startups versus maybe the bigger companies that you were with?

Yeah, never really worked at a big company that was solely through an acquisition. I was at a 100-person company that they bought. I always liked being at that A round. I felt that that was where it fit, even though it wasn't depending on the territory they gave me. But I liked smaller companies, less bureaucracy, very tangible results between effort and reward. And a lot more freedom. I found that the bigger companies, either that I interviewed with or had friends at, the BS was just such a large percentage of the job that I had no interest in that. I did not want to move up in the company. I wanted to make money. And although I tried moving up a couple times, And I kept asking myself, why am I doing this? It was just something that I felt obligated to do, that it was the next step in my career. And it just became more work, less money, and a lot more headaches, which were going against what I liked doing. I liked closing big deals, getting into new accounts, killing our competition. That's what excited me.

Yeah. Love that. I had a little bit opposite approach. I was always at big companies and then did a little bit at small, but Interesting to hear that perspective. And then as you progressed, you eventually kind of obviously went into your own thing. What were those, I guess, epiphanies or how did you decide to kind of start your own thing later on down your career?

Well, I think like a lot of people, you kind of obsolesce yourself, meaning you get to a point in your career where you start working for people with less experience than you. And sometimes you pick them when you, when you go out and get a new job, and sometimes they're pushed upon you where you get that job and then your manager changes without anyone asking you. And when you start working with people who are less experienced than you, they think just because they have the role that they know more about the job than you do. So it's like inverse coaching. It's like you got this person telling you to do the wrong thing, and if you don't do it, they make you wrong instead of them wrong. And when you do that a couple of times, it becomes so frustrating because like the last time the CEO brought me in, he used to be my boss at a previous company. We had mojo, we got along, we knew each other. We spoke the same language, but I didn't report to him. I report to some goon that he had running sales who, you know, I wouldn't hire to park my car, but I report to him. So, you know, he, oh, he just got in the way, would end run my deals, muck up. And I'm like, I gotta go do something else. But I love selling and I really was a process guy. I wasn't one of these magicians where I can't tell you what I do. I was the opposite. I could— I was much more of the mechanic. I can tell you exactly what I do and how I do it. And I got to believe that there's a market for this because most of what I saw was random acts of sales rewarded by the market versus intentional sales that were rewarded for effort and execution. You go to a startup and somebody had a friend at the company and they get that seed deal and it was at a great company and it blows up. And is that good salesmanship? I guess networking, some value there. But I was much more of, okay, I know this company can use this. This will change how they do business and I will find a way of getting in there. And it was creativity and persistence. And I knew I could teach this to other people. And I had a passion for that and I had a passion for, you know, beating competition, doing big deals and helping people who wanted to be helped. So, and, and plus I was also at a point in my life where I didn't have to work. That's a, that's a big privilege.

It's a good place to be.

Yeah. So I didn't have that desperation where you're like worrying, you take the bank account and you amortize it off your burn rate so you know how long you have a runway. way you have. I didn't have that problem, which gave me the chance to do it the way I wanted to do it, not the way I had to do it.

Yeah, that's a great place to be. And I appreciate the fact that you enjoy helping people that want to be helped from, from a sales standpoint. When a lot of people know you for kind of your walking and talking videos, and of course your podcast, what made you start I guess using social media and doing some of the videos, was that just something that kind of came about randomly or was that something that you really kind of focused on and wanted to do and you thought it would be a game changer for you?

Well, I started doing the videos in like 2012, so it was almost 10 years before the videos on LinkedIn. I was just doing them on YouTube. I didn't do anything on comedy though. I was doing on, you know, sales tips, and it got some traction. But the, the choice I had was, do I want to go just with my word-of-mouth marketing, which was very labor-intensive, uh, unpredictable, and not a whole lot of fun, you know, just prospecting constantly, you with people. And if you're doing that, that's— it's cold outbound. And you're hoping that they want help. But a lot of times they just wanted to fill a slot. Or managers would say, can you fix these guys who don't want to be fixed, who think that you're the problem? So you became like a family therapist going in a lot of times. It's like, hey guys, can we talk? You know, why aren't you doing the dishes? You know, it was like this foolish little intervention. That wasn't what I wanted to do. I wanted to talk with reps who wanted to sell more, who wanted to talk with somebody who knew how to sell more. That's where the fun is, you know, hearing about people's problems and finger pointing and being Dr. Phil of sales wasn't my goal. But the videos, what really flipped it and exploded, I think, the awareness of me was when I did LinkedIn videos and then when I did comedy on LinkedIn because sales is such a political, religious topic to people. And most salespeople, you know, about 30, about a third are know-it-alls. You know, I've done the survey a bunch of different ways. It's about 33% think they know everything, and that's okay until they find out they don't. It's good for their confidence, but it's terrible for their selling skills. So I'm not— never going to get them. So that gives me two-thirds that I can get, and most of them want to laugh first. And if, if, if their introduction to you is a pleasant giggle, they're open to what you might say about sales, especially if you can merge the two together where you're making fun of something that's bad about sales and showing how you should do it, but with humor.

Yeah, that's not an easy transition to make, but you've done a great job of that. And I know that's how I originally found you was Those videos and, and then the podcast, of course. As far as your, your schedule, I know you have a lot of things going on with, with the videos, with your social, with podcasts, your courses. How do you kind of prioritize everything and, and be effective? Is it things you do first thing in the morning, or how do you kind of map out your schedule in your week to, to get the most things done?

You know, I, I have a certain list of things that, you know, have to get done. You know, a couple of episodes of the podcast, a bunch of one-on-ones, the office hours every Friday. And if, you know, everyone says time blocking, but if you put it on your calendar, but don't overbook your calendar because if you overbook it, it becomes very easy to let things slide and then things always slide. It's like a workout, right? You take one day off and then all of a sudden it's 2 and it's 2 weeks and then you're out of shape again. You know, like I gotta tell you, the number of office hours that on Friday I feel like doing isn't that high sometimes. So it'd be very easy to let that slide, but then it, it would never come back. But if you do it every Friday and then all of a sudden you, you fit in, okay, Monday, pick a topic, Tuesday, map it out, Wednesday, come up with some other examples for it, it becomes pretty simple. And like the walk and talks, I'm out walking anyway. I like going out walking or running. I'm gonna have my iPhone with me anyway. So why aren't I asking myself about ideas? And the best ideas come from other people's bad ideas. And there's so many bad ideas out there about sales. There's endless amount of material. And why not record it? You know, so I have like Otter on my smartphone and I, I'll be running and I'll have an idea and I'll just talk into it and jot down the idea. Then if I go walking, it's like, okay, how do I turn this into a video that's interesting in a minute and a half? Sometimes it clicks, sometimes it doesn't. But if, if you just have the, you know, the, what is the minimum I need to do every week? And then you have a lot of time to do the extras. See, most people do the opposite. Like, how do I get the most done every week? And they end up doing a lot of busy work, not a lot of tangible, you know, asset-based work. So I always think, what's an asset? An episode of the podcast is an asset. Hopefully it's evergreen. Someone can listen to it 10 years from now and still get value out of it. Busyness is, you know, commenting on someone else's post, getting into a fight on LinkedIn with some stranger you'll never meet, reading something about a new technology you'll never use. That can take up a lot of time. But if you focus on purely what are the things that you need to get done, and a career in sales hopefully gets you super focused. Because you can waste an enormous amount of time in sales. You have to be hyper-focused on, because it only matters what you close. Everything else is academic.

Yeah, some great points there on habits and consistency. And I think when you're outside walking and running, a lot of great ideas come to mind typically. So it makes sense that you're combining both together. So That's awesome. Kind of flipping a little bit. Obviously you've interviewed thousands of salespeople at this point, probably even more than that. What are some of the common traits you're seeing with the top salespeople lately, the last year or so? Is there any commonalities that you're seeing with sales reps right now as far as the A players go?

Yeah, I mean, the A players, it's very consistent. They don't act like salespeople. So they're not dab dab dab dab dab. Hey man, blocking and tackling. You know, they're not you know the keyword generators. Those are the C players. The A players really understand what empathy is about, and empathy requires a great deal of confidence because you're going to be asking hard questions. You got to be curious. To be curious, you have to be confident. You have to say, tell yourself, I don't know it all. And I used to have this question that I asked myself before every sales call: What do I want to know that I don't know now? Those became my questions. Everybody else was focused on what to tell them about the product. I know about the product, that they're not gonna stump me on the product. I'm gonna stump myself because I didn't ask enough questions. And I found out really early in my career, mostly because I did not wanna stand up in front of everybody with 50 slides and sit up there and sweat for about 45 minutes telling them why we— this is our building and these are our founders. I never opened the laptop.

I would—

don't, don't turn on the projector. And I'd have my questions and I'd show so much excitement, enthusiasm about them. The hour would go by with no presentation. And then I knew enough that when we went back again, we could have a presentation that was completely customized to what they told me. So it was even more engagement. And my manager would get a little, we really didn't talk about the product enough. And I go, well, they're not gonna buy it because of what we're gonna tell them. They're gonna buy it because of what they need it to do. And they wanna meet us again. That's the objective. This is the complex sale, not the simple sale. We walked off the lot, not them. They want more. That's what we want.

Yeah, that's great. I think there's a lot of death by PowerPoint out there, and especially the, the mission, the, the founders, the company at the very beginning of the slides too. So that's, that's definitely the way to go. And that kind of transitions to this next question is, what are you seeing out there now that you think is wrong with sales or some of the negative trends going on? And we don't have, we only have a little bit of time left, so you can't do everything, but what are the top few things that you think are not going well in sales right now?

I think everybody wants to turn it into a revenue machine and there's some products in some markets at some stages where you can do that. But if you're, if that's not working, that's probably why it's not working. And you can almost tell by the The ages of the people that they hire. Everyone's focused on the cost of sales instead of the amount of sales. No CRO ever got fired because their cost of sales was too high. They get fired because their sales are too low. And it's just crazy that people cannot see this. Maybe they were raised through this. We're selling a product. It doesn't matter how much time you spend with people who will never buy. That is a waste of time. And the overfocus on data and dashboards and KPIs is reducing revenue, not increasing it. Our job is to increase it. That seems like an epiphany to some people. Because their managers want to see the same bullshit that they're asking the reps for. Make it up the way you made it up when you were a rep. They all know you're making it up. Just give them their toy to play with in their meeting and then go out and sell something, because they will not get fired when you miss your number. You will. It's about selling. It's about customers. It's not about the number of contacts in your CRM that are— you've contacted who will never buy. Think about your CRM. What percentage of the records in there will become customers?

Not very many.

It's not more than 1%, right? That means the other 99% is a distraction. And people think, oh, it's in my CRM, there's some asset to that. Not today. If I want to get in touch with somebody, how long does it take to find out their email, their phone number, where they live? Less than a minute. So the power of having it in the CRM. Oh, what happens if they leave? Oh, I don't know. We still have the internet. Oh, oh, we won't know the last time they left voicemail for them. This is the fear. Like there's some context that you don't have. It's about selling and that has been forgotten. And I had an interesting interview yesterday where they brought a trainer in because they think selling is building interest and that's a step in sales. And then I asked him, well, where does your sale get stalled? Is it Going from curiosity to interest? He goes, no. I go, let me guess, it's right after you send the proposal in, right? He goes, how'd you know? Oh, I don't know. How would I know that? They're solving the wrong problem because they think it's a simple sale. If 80% of the proposals that are sent out for the people that are dying to have it don't close, you don't understand your game you're playing. You're playing the wrong game. You're playing softball when they're playing hardball. And people think it's a, oh, it's they're not a good champion, or the timing's not right, or, oh, we're not on the right priority list, or you don't know how to sell. Which one do you have control over? Which one do you have 100% control over?

You.

That's what I see missing.

Some good ones there. Some good ones there. Some great advice for everybody. And kind of wrapping up here, a few more questions, but I guess for those younger folks who are maybe considering getting into sales or maybe they're early in their careers, is there any advice you would give to some of those younger folks of, you know, some things they can do to kind of capitalize on their career and do things the right way? Is there anything, I guess, going back for yourself that you would do differently and kind of recommend to some of these younger folks?

Yeah. I mean, definitely get into business-to-business sales. I know you can do okay in B2C, but the upside just isn't there over and over again. But once you get in, find the person who shouldn't be successful, the person who doesn't look or act like a salesperson on the floor or on the team. But yet they're doing really well. They're not the grinder, but you— no one understands why they're doing well. They might be a lone wolf, doesn't matter. And go befriend them, interview them. They're not going to know what to say sometimes, but pull it out. You know, go through a deal that they had that wasn't a slam dunk. It wasn't warm inbound beauty contest. You want on given the lowest price the last day of the quarter. How'd they get in? How'd they stay in? How did they beat out their competition? How did they get the deal so big? That's what I would do. Too many people— if you have a great manager, great, but most managers out there are really admins with a manager title, and they're following what all the other admins do. Count this so that we can have this little funnel, and the math is real easy to diagnose where things aren't going well. Oh, your conversion from demo to proposal is 2.4. It should be 2.6. Oh, now I know what to do. More proposals. This is the stupidity that passes for sales leadership today. So I would, if you want to go into sales, go into B2B and become a student of the game. Don't read B2C sales books. They set you in the wrong direction. Don't listen to Grant Cardone on YouTube and go, that is not going to help you sell more. Study how companies buy and how they change.

Love that. That's definitely the way to go and great advice for the younger folks. And last question to wrap it up is, is there anything that you want people to know about you that maybe they wouldn't know or something unique that you would want to tell the audience that maybe they've never heard before?

No, I pretty much pretty open. Oh, the brutal truth. There we go.

Brutal, brutal truth. And, and they know where to find you. I know we usually end with where to find you, but if you don't know where to find Brian at this point with his podcast and LinkedIn, then you're doing something wrong. So appreciate it, Brian. It was great to kind of hear a little bit more about your background.

See, anyone could become good at sales. I'm living proof of it. And boy, what a journey it's been. I think everybody, when they first start, either is either way overconfident or way nervous about it. And some of us, we grow into it. I was more the grow-into-it type person. But what if you become a student of the game? What if you start studying each sales call? Look for patterns and try and really analyze them, thinking like a detective, really wanting to understand what you're doing right and what you're doing wrong, and get on this journey to sales excellence. Because that's where the fun is. Because the first few quarters were not fun. I remember going to the doctor, and for me to go to a doctor, it's life-threatening. That first year in enterprise sales, it was 100% because of stress. It was nothing, you know, no disease or anything. It was just stress-related stuff. And it was being put under pressure by myself, by my boss, by the situation. And you figure it out. You really sit down and you analyze. And I took what I was good at on the software engineering side, which was breaking problems into smaller, tiny little pieces and really thinking through each element Of it and working off of my strengths, not my weaknesses, and augmenting the weaknesses with other people within the company, doing the best I can to cobble together a great team to win these deals, to motivate other people to help me do what I was not good at. And it took a while. And believe me, not each job was A walk in the park.

Most weren't.

Most were really hard, and most you had to prove yourself over and over again because they didn't know you or they had doubts about you or—

I heard it all. You're too young.

You're too technical. You're not technical enough.

You're too old. You're too this. You're too that.

And A lot of us hear that and a lot of us believe it. Now, if you believe it, then it becomes true. If you fight it and you work around it, then it just becomes a speed bump on the highway of life. And I think that's how you should view it. Because if you have the, you're too this, or you're this, or you're that, in your way in your career, Make a decision. Either I'm going to believe that and go with them, or I'm not going to believe it and I'm going to prove them wrong. Not purposefully, just go out and get what you want out of life. Everyone can think whatever they want about you or me or anybody else. They're right, they're entitled to their opinion. Doesn't make them right. We can create the life that we want in business-to-business sales. It is a beautiful career. And, you know, I look back and I go, what would have happened if I stayed in engineering? You know, would it have been bad? Probably not. I probably could have grown into a reasonably good engineer, but it was a passion of mine. It wasn't like I disliked it at all. I loved it. But I loved the control I had over my time, my money, the direction I could take, the freedom, that independence. That's pretty exciting. And being able to stock away a bunch of money to have a lifestyle that you want, options, choices that a lot of people don't get if you, if you're really, you know, working paycheck to paycheck trying to fund the 401 for 20 years from now? How about if you could make a lot of money every year? That's why we're in sales. And that's why we should be in sales. There's nothing wrong with it. A lot of people diminish it. Oh, you should be in it to help people. Join the Peace Corps if you want to help people. Go work at the Animal Rescue League on the weekends if you want to help animals. It's all good. There's nothing wrong with it. But there's nothing wrong with making money either, being successful, beating your competition, helping your customers out, selling them the product, the best product in the market. Hopefully that's all part of your jam. I hope you enjoyed this little diversion of the podcast, bringing a, you know, B+ player, maybe, hopefully. But what I teach in the courses is how anyone can learn how to sell.

It's not the polish, suits, fast talking.

It's about guiding somebody through a journey, but you gotta know what the journey is because they don't. They think they do, but they don't. We think they do, but they don't. And we tend to follow them and we shouldn't, but we do. And when we do, It doesn't close. So we need to learn how to lead them through it, guide them, help them, show them the way. And that's what Closing the Complex Sale is all about. But if you don't have enough stuff to work on, enough good deals, hot deals, interesting deals, you may want to get— start the conversation, get the meeting. It's always a good place to start because We all kind of fall into that rep trap, don't we? You know it. Oh, tell me what you do. How's it work? What's it cost? Thank you. Send me a proposal. We'll let you know. That's the rep zone. You don't wanna be there. You wanna have conversations, deep conversations about how they ended up where they are. Why are they there? How's it working? What are they up against? Tell me more.

I'd like to—

I'm interested in that. That sounds exciting. What keeps you there? You want them talking. You want them to want to talk with you, not have to. Start the conversation, get the meeting. Teaches you how to be a salesperson. All the stuff I see on LinkedIn and YouTube teaches you how to be a sales rep in the rep zone, and they just walk you right into the trap lock you in the trap, and then they have another video about how to get out of the trap. Well, it's too late. You're in the trap. Any getting out is not very good. It's all about never falling into the trap. Quit acting like a sales rep and start acting like somebody they want to talk to. We'll see you next time. Make sure you're checking out the other show, Sales Questions, Brutally Honest Answers, The Best of the Brutal Truth. And the Sales Leadership Show. We'll see you next time.