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Let's get into the interview.

Hey, John, thanks for joining us today.

As a way of getting started, give us a little background on yourself.

Absolutely. Thanks for having me, Bryan. I'm John Silverman, born and raised in New York City, currently living out in the LA area. I've been Director of Sales at Sky, formerly known as Kenshoo, for about a year and a half now, a little more. And I started my sales career in like straight ad sales, advertorial sales, pay for play, as it was used to be, as it used to be referred to. And from that, I grew into, in a weird way, I peaked too early as a, as a manager of 23 people when I was myself 24, and then humbled myself by working at a place like The Economist for 7, 7 months to understand what a real, you know, AE role looked like. And then, and then I got into SaaS, and that's kind of where I've laid my, laid my hat for the last 6 or 7 years. And I love software as a service, whether it's in the ad tech universe or elsewhere. It's something that really gets me going.

Cool. And why sales leadership? What you like about it?

Currently, I'm an individual contributor at Sky. The director might be a misnomer, but I'm a client partner at Sky. I've been a head of sales 2 different times, 3 different times in my career at startups that have no seed funding to well-established growth, high-growth startups. I was actually on a business trip in London for a startup that told that they didn't get the funding that they had already said that they had. And I was told that I was no longer affordable while I was on the business trip in London.

Nice.

Yeah. So interesting, interesting, interesting sort of up and down. I have fluidly gone between IC and leadership without much ego around it, I think because of that early role I had, which made it so I was sort of a peer or younger than most of the people that I was managing. And it was a lot of work. You know, one of the questions that you had asked in some of our email correspondence that might be something to talk about is like, what's a misconception about sales that people— and I think one of the things that people who get into sales really want is to become a sales leader super quick. And they just don't know what that entails, right?

Yeah.

Half of it is the empathetic. I want to be a leader. I want to motivate. I want to help people through what they're going through. I want to take from, you know, poor performer to great performer or from good to great. That's half of it. The other half is the managing up the expectations and the constant need to kind of keep doing new things constantly to find where your rhythm is.

Well, also, and especially today in SaaS, the metrics have become a science experiment. And if you don't— either you don't have or can't afford a sales admin or sales RevOps person, you become that person. Or yeah, you torture the reps to enter all the data that's mostly made up and have to report it.

Yeah, I was just watching your video. I'm not sure when you made it, but it just came up on my feed about we just closed our round C and now we need to increase ARR. And you're, you're, and you're like, you mean, you mean revenue? Like what we've been doing the whole time? Yeah, but ACV though. And it's just, it really resonated with me because You know, your point also about increasing quotas from a different video, it all comes together with, with these expectations with, with VC money, um, where you have to have 100% year-over-year growth and you have to exhibit, you know, this in net new and this in retention. Um, it becomes a bit of a race to the top where the top becomes how much higher can you go? Uh, that's the question I ask.

Well, you know, because I work with leaders all the time and I—

they start going down the acronym And I go, well, let's stick with revenue and new customers. Something we can focus on.

Yeah, I mean, it's the lowest common denominator.

And everything else, you know, you can get some, you know, hire somebody for $50K to fill in the elements and keep track of it. I'm not against it.

It's just like, where does it fit in the priority list?

Right. Speaking of priorities, you just were talking about like Salesforce admin, sales ops admin. Another one of my favorite SaaS leaders, Scott Lise, very famous for saying, that like the number one hire for a new VP of sales has to be a sales admin, sales ops admin. Helps you build everything from ground up, helps you get a clear understanding of what's going in, what's going out, you know, metrics, also not just performance, but also your KPIs in terms of like outgoing calls, outgoing emails, etc. If you don't have that view, to your earlier point, you're basically just drawing things on a piece of paper and hoping for the best.

Well, or you become the sales admin.

Which is even worse because VPs of sales are not good at sales admin.

They're not good at it and they have the real job.

Correct, of driving sales.

Right, because at the end of the quarter you can't say, well, look how good the dashboard looks.

That's beautiful. It's clean. It shows the blood number right there.

You'd rather say like, oh, revenue was good, I fell down a little on the metrics.

Right, that's, it's an acceptable sacrifice. But I think a lot of sales leaders in the SaaS world from— let me start over— the more desirable sales leaders from the SaaS world these days are data-first, which is, is good and has its obviously obvious drawbacks. One thing I see from that, having been a SaaS leader, and then having left that company and been replaced by a data-driven sales leader, is that you have a little bit higher churn on your, on your employees. You have a higher, longer ramp-up period to get to your most efficient production numbers in terms of an AE. But what you do have is a great dashboard.

And it becomes— you become an accountant instead of a sales leader. And it's real comfortable because the books say it, the consultants say it. Because it keeps them busy.

There's a lot of spinning wheels in terms of non-specific direction based on non-specific numbers to get to a non-specific goal.

Right.

That sounds really good.

And when I talk to salespeople, they, they just hate it because everything's being counted but nothing's being accomplished. Right.

That's as a— sorry to cut you off again.

But one of them can be faked. One cannot be faked.

That's kind of what I was just gonna say. You know, action is very visible. That's why salespeople are motivated, at least I am, by accomplishing things, by getting, you know, the feeling you have when that email comes across of like, we're ready to move forward. You get the goosebumps, you have an action point, which is to build the contract if you haven't already, push it through the legal. That, that is accomplishing things. And then obviously, when you secure the client, helping them to achieve their goals. That's, that's something that you can really take to heart as an accomplishment for sure.

And are you comfortable being an individual contributor? Do you like it? Is that where your passion is, or is it only on the path to becoming a leader?

It's a very interesting question, and I think my answer is the least ideal for most people because like I said, I've been rather fluid throughout my career. So I'm very happy and comfortable in my role at the moment. When I say comfortable, I mean, it feels comfortable. I'm always chasing the quota and making sure I have a huge pipeline, etc., for whoever's listening. But, but what I mean to say is that my prior role, I was the head of sales for a global company with 30 direct reports across 4 or 5 different continents. Now I have no direct reports and my territory is the West Coast and it feels good is what I mean to say. So I don't— I'm not missing that. Yearning for that. However, what I've learned even in this individual contributor role, having dealt and closed some of my largest deals, if not the largest I've ever closed, it has taught me a lot of things that will be helpful to be a leader again. And I know that I have the foundation on the empathy side, on the growing side, the mentorship side, and the accountability side to already, you know, handle that. So being able to really see through, you know, the biggest enterprise deals I've ever seen before managing You know, 16 different teams helping out. It's, it's taking villages to do this, uh, will form me to be a great leader if and when I choose to, you know, become one again. It's not, it's not as if people haven't asked. I just am— I'm, I'm pretty happy.

And I've also noticed, like, because I, I went up and down from leader to rep, when you go back to being a rep, you're so much better of a rep.

Exactly. Yeah, you saw a lot. Yes. You also have this worldview of like, not just the tunnel vision of me closing the deal and linearly doing the ABCD things necessary, but a bigger perspective around these deal terms are going to do what for, you know, legal or finance? Do I need to get approvals? Do I not? Can I get this through in this way? Can I formulate the deal in such a fashion that it'll get approved? So and Also asking for help, being able to ask internal people for help in such a way that they always want to is a really, really good skill I learned as a leader.

Yeah, because you develop— you have to develop that internal—

The internal rapport is almost as important as the client rapport, because if the client says yes, you then need to leverage your internal rapport to get it done, especially if it's custom, especially if it's custom.

Anything out of the normal. Yeah. And what have you learned along the road as far as a sales rep? Because now you've seen other reps, not just worked with them, you've managed them. Have you come up with a formula or a—

I think that if somebody did come up with a formula, they'd be the Google of finding salespeople. That's the beauty of sales. There is no archetype. There are archetypes, but there is no single. I love some of your polling about, you know, how many A-players there are. What does it take to be an A-player? Are you an A-player, etc.? I think there's 2 different types of potential A-players. There's the A-player that is an A-player out of absolute drive, dedication, effort, and will. That's the hard worker. There also is the A-player that is the ability to do things easily, doesn't necessarily need to apply themselves 100% because they are able to get things done. according to the comp plan, to the quota, to this, to that, but also a wizard at relationships, right? That's the key point. There's the hard work and then there's the key relationship holder. I find myself a little bit more on, on the latter as opposed to the former, um, but there's no, there's no escaping the fact that you need to be a really hard worker to be a good salesperson. And I, you know, one of your other questions that you had asked that was a thought starter for me is like, what is What do people not get about your job?

Forget it.

Like, my friends forget it. Like these videos that I see on the internet of this was a real cold call, the anger, the defensiveness, the odd— how could you call me? Well, because you're the head of marketing for a major brand and you spend tons of advertising dollars and we help out with that. Is it really that much of a shock? So I mean, like, what I mean to say is that people don't get just the difficulty of breaking into a company, much less convincing them to spend tens of hundreds of thousands of millions of dollars.

Yeah.

And are you feeling over your career that people are less and less likely to engage with a salesperson?

Because I think, you know, certainly the cold call with the cold pitch You know, I think the days of like picking up the phone and dialing for dollars are probably nearing its end for most industries. There are certainly industries where you can pick up the phone, dial it up and hit 100 people a day and find 10 people interested, certainly. But in enterprise SaaS, I'm not sure that that's really the method anymore. Like, you know, first couple months of the pandemic, I would send out emails, and I would send out LinkedIn notifications, and I got like multiple things back that were like, this is tasteless, how uncouth of you, how dare you, people are losing their jobs rapidly. And I actually put a post out on LinkedIn that it was like, I think the dynamics changed here a little bit. Like, everybody was losing their job at the time, not just salespeople, not just marketers, not just service workers. Everybody was losing their jobs. So there has to be some element of baseline humanity, where we all understand that if we have conversations with each other, there's a higher likelihood that we're both going to have a job when all this is over. It was kind of like a flight or flight moment, fight or flight moment. Some people reacted very poorly to that. Other people engaged, and we formed partnerships because of it. So I think it really depends on personality. But to your point, like, the way you engage with people is a 17-step Cadence or flow. They will respond maybe by the 8th and a half touch. And then maybe you get them with some great content in one of those emails, hopefully make it personal.

Well, you know, because that's kind of the number one thing I hear from reps is that, you know, cold outreach is just ground to a halt.

And hard to— there's no desk, there's no desk phones really for the 100% remote workers anymore. People don't put their cell phones out there. It is hard. It is hard. Absolutely.

Right. And, you know, if they happen to pick up the phone, they didn't do it to talk to a salesperson.

They certainly didn't. And that's where I love most salespeople's traps, saying like they get surprised when they get a pickup and the first thing they say is, how are you? That's going to open up a Pandora's box that you don't really want to know about. And as a matter of fact, you don't really care. You don't. You just want to talk a little bit about what you do to see if it's a fit for the other person. And I think a little bit of that— I tend to speak to my prospects very much how I speak to my friends, meaning I don't have a professional voice. No, I hate to do it.

Well, I did a video on sales voices and it's like nothing kills it. Because it's like, you know, it's like going up to somebody in a bar and asking what sign they are.

It's a true— it's a tired, very, uh, uh, obvious tactic.

It's, it's screaming, I'm a salesperson and I'm here to take something from you, right?

As opposed to, you know, I— the first job that I had in sales, um, was when I lived in Europe, and it was for a, a steel brokerage company based in LA. Weirdly, they had me open up a Central European office, and my job job was to go and secure steel production in Central Europe. It was an amazing job. But my first media sales role was one where cold calling was the only way that we got in touch with people. And this was in 2009. And I think that maybe when Outreach and Salesloft and these types of sales enablement tools started coming to preeminence is when cold calling started to have a diminishing effect. Otherwise, why did these companies come to unicorn status, right? I think there's a, there's a cause and effect there.

Well, and management still thinks it is effective because it worked for them in the '90s, right?

Just pick up the phone. Just pick up the phone. Like, why haven't you called them? And the amount of sales managers that have said to me that everything can be totally taken care of with a phone call, like, yes, obviously, Sometimes, well, not obviously, sometimes it could get even worse. What I mean to say is that I had a cold call once where it started out really, really well in terms of we were talking about the industry. And that's what my first sales job tried, though. This was what I was trying to say, my first sales job, my first media sales job. The point was we were positioning ourselves as industry experts. So for example, I would be doing a project about, you know, type 2 diabetes pandemic in the USA, 24 years old, graduated college with a political science degree, less than 2 years earlier, but I'm an industry expert in diabetes, and I want to talk to Johnson Johnson about it. And that at least got me into the PR and the comms teams, which then almost certainly got me a conversation with marketing. So anyway, I did have sales personas at some point, but I found that being a genuine person in enterprise SaaS sales is a way better, way better option.

Right?

Because I mean, how many times during the day do you— are you lonely? That, that talking to somebody about you, not them, right? People still pay. You know what though, one of the biggest businesses— That's a great point. Is online therapy.

Oh yeah, Talkspace and, uh, and some of the others, Betterment.

Yeah. Right. And you know what the therapist is doing on the other end? They've got their little list of questions. Well, how's that make you feel?

Talk therapy, you know, a lot of people do it. And I think it's, it's very valuable. But to your, like, to your point earlier about sales, like, there's action and then there's talking about action.

Yeah.

So, you know, take, take it for what it's worth, I suppose.

And what do you, or what drives you? What excites you? What keeps you going?

Um, this is like the age-old question, and I think, and I think there's another misconception about how the external perceives salespeople. Everyone thinks that we're just like money hungry. And when we win, it's because we've taken the client for something more than they thought they were. And we, you know, that's a terrible misconception. And I really, I blame Alec Baldwin quite a bit from Glengarry Glen Ross. But the real motivation for me is helping people. And a byproduct of helping people is making a lot of money, being successful in sales, Because in order to help them, I have to sell them something and then that product will help them. So I try to make the umbrella motivator helping people. And so when I hear from somebody, you know, 6 months down the road after the contract was signed, like, we're seeing incredible results, we're gonna add another channel to you, we're gonna do this, we're gonna increase. It's really, it's what I set out to do. And of course, the byproduct is even more money for the upsell.

Yeah.

And what keeps you motivated?

I think now, as an IC in enterprise sales, it's the bigger behemoth, the massive global brands that normally for everyone else, including me, potentially takes 9 months to a year to close. Finding a way to get those done, finding a way to get them done quicker, finding a way to I don't know, I take a lot of pride in being able to like bypass certain things in the procurement process, whether it's because I have a great relationship or whether it's because we've shown prowess in our product. You know, last year during the pandemic, we were cutting— we, the collective, myself, the client, everyone— we're cutting corners because no one was in the office and we really just had to kind of make do with what we had. Things still took a heck of a long time, but being able to get on the phone with like the general counsel of a Fortune 500 company Explaining what we do, having them nod their head along, asking, you know, intriguing questions. That, that's a cool thing for me. That keeps me motivated.

How about as far as like the building of resilience, especially in the early part of your career when you was like ad sales where it was kind of a grind, tons of—

I mean, the leathery skin just got leatherier and leatherier. I mean, it's— it was battered by the time I left traditional print sales. I think the resilience is— the resilience has changed from I have been said no by the gatekeeper or junior person so many times, and I need to be resilient in going back to them. That's changed to, I need to be resilient in, in my patience, in understanding that big decisions take big amounts of time. So if I'm working a few major big deals, I need to make sure that I have a few minor to mid-sized deals so that I'm keeping busy, keeping motivated, helping other people in the meantime, and keeping my eye on the longer game prize. So resilience, and resilience as I've grown older in my career, has turned into being a proponent and an adherent more to the long game.

And we talked about gaming before we started this. Do you look at sales like a game?

I tend— I think this is a personal thing. Everyone has the personal thing, but I tend to gamify most everything because I, I live my life on a goal-reward type basis. That's having— that's having— that's the result of having a pretty strict single mother as a parent. But I orient myself in a goal-reward sentiment, meaning very simply, even on a day-to-day basis, I'm gonna get these 3 emails out, they're going to be amazing. And then I'm going to take 10 minutes to have a snack.

Yeah.

I run my life like that. So I think that gamifying your job is a way to keep it Interesting and a way to keep it motivating and fun.

Well, it builds that habit so you don't have to consciously think about it. It's 3 emails break and—

15 minutes in Salesforce without wanting to jump out the window. Yes.

Right. Instead of the, you know, the high calorie, what do I do now? What should I do?

That was more of an in-office when other people are watching you Yeah. You know, salespeople aren't supposed to be in the office anyway. So whenever, whenever they are, unless you're an inside sales team, no, no, no doubt about that. But as, but as a sort of enterprise outside salesperson, it's when you're in the office, the eyes are on you, because what are you doing here? Unless you're like moving deals forward or doing this or that, like, get out. But ever since, I mean, I haven't been in an office since March of last year. Ever since then, the shift has been to Let's talk about your Clari call. Let's make sure your notes are up to date. Let's make sure your outreach, not in a micromanaging way, but like for the first time, my manager talked to us about outbound emails for the first time in a long time, not in a negative way really at all, but just as a means of saying like, I'm a new VP who's never actually met any of you in person. She's, I mean, she's been there for almost a year now. She's fantastic. I really enjoy working with her. But I've never met any of you. We've never had the chance to be in the office together. How can we talk about something that makes sense to all of us so that we can have some sense of how we're doing? Because we do need to, in fact, move things forward.

You know, we—

Sky acquired a company at the end of last year. We rebranded earlier in the month or late last month. You know, we're clearly making moves. So the importance of maintaining that steady pipeline by whatever means necessary is really important.

Yeah, because I think if managers did more of that, kind of engaged reps in judgment skills, you know, what's working for you, you know, what's your system like? You have gamified your day to keep the activity consistent, get stuff done.

Absolutely. Where am I on the leaderboard? Yeah, there's an element of competitiveness to that as well. When I was head of sales at my last company, There was, to your point earlier, like there was no dashboards, but we did have a good Salesforce admin and we whipped them up lickety-split. One of my first things was we had a New York office, LA office, Paris, London, Sydney, or sorry, Melbourne. I wanted screens in every office showing like revenue, opportunities created, number of emails sent, number of meetings held for everyone in the company on every screen. Just so that there's some element of like, ooh, even at the most basic level for a non-sales or marketing employee, ooh, that's a colorful screen up there. What's that? And then I, in front of 8 of my reps in New York, would have been able to say, well, thank you for asking. That's where we're all at in terms of— and oh my God, look at you, Brian. What, you know, what happened between last week and this week? And all of a sudden you have a conversation that's a little bit more lighthearted because it's in front of a group and it's not necessarily a serious, you know, performance-driven conversation where they get up, come away from that conversation feeling, all right, I gotta work to get my numbers up. That's, that's kind of the effect there.

Well, that's also kind of an innate motivator, you know, social status, competitiveness.

Yeah.

And that certainly drives me because I know that if I look at one of my competitors, it's going to get me— it's like a cup of coffee. All of a sudden now I got a good 45 minutes of, you know, energy and spite That I have to—

and you take that, you take that spite, turn it into the energy to get things done.

Right. And I know that about me. And, you know, I'll leave the window up. So the next time I open up the browser, it's my competitor. It means I got to work more.

Oh, you got jolted again.

Yeah.

And that's great.

And I think that is one of those elements about the A-player.

When I hear somebody not being competitive and not really caring where they stand, Yeah, the academic salesperson who comes in and says, I don't really mind about where I am, I just really want to get things done and I want to, you know, work with big brands and stuff like that. Like, if that's true, then, you know, a little bit of a red flag for me. But some of those people will say that and then turn out to be some of the most competitive people I've ever met, actually.

Well, you know, like I did this poll about, you know, what motivates you more, the, you know, the victory of winning or the agony of defeat. Avoiding the agony of defeat. And I don't care about the answer. What I look for is the emotional attachment to one or the other.

Yeah.

You know, the people who are kind of like even-keeled, and that's fine. They probably enjoy life more than I do, but they're not going to stretch. You know, they're not going to be working at midnight trying to figure out how to win this deal back or how to keep their competition out. It's that emotional connection to the outcome Whether it's avoiding losing or gaining, it doesn't matter. It's an emotion.

I really track with that. Well, like, me and my VP were up on June 30th. It was Wednesday. It was like 11:40 Eastern. And we were working to close a deal that was a competitive steal. And the CEO was up. I mean, it was only 8:30 Pacific. So we were still sort of up and we got it done. And We have talked about, it's not a big deal, but we have talked about that a couple of different times now because of the way it made us feel and the emotions that we had in getting it done before the deadline and taking it away because of the deal terms we made, et cetera. So I think, I think a great example of what you just said, the fear of avoiding the fear of losing to the thrill of winning. Do salespeople care tremendously when a brand that they haven't yet reached out to gets snagged by a competitor? Not really, because you haven't reached out yet. But if you've reached out or if you've had contact or if you've done a demo or whatever, and then they go, that is the worst possible feeling that you can have. So I think the emotional tie-in to what you, what you were saying, I think the fear of losing is most applicable when you have had a relationship with a prospect.

And you also have to be cognizant that early in the sales process, you can't be that emotionally attached to it.

The first no I ever got, like 2 days after I got my computer at my first media sales job, was from a media buyer in San Francisco who obviously had decades of experience. And here I am, like fresh, green as can be. And I was worried. They were like, yes, yes, yes, it's going to happen. Then it was like last-minute budget changes, which I didn't yet know was like the be-all end-all answer for just no. And I started an email. Thank God my colleague caught me. I started an email that had like 6 question marks after the first sentence. And she was like, whoa, whoa, whoa, whoa, whoa. This is your first no here ever. Let's have a beer. Let's talk about this. Do not send that. And so you're right. I struggled early in my career and I sometimes still struggle every once in a while with getting emotionally attached, especially to these big enterprise deals that you've spent 9 months talking to somebody with. At some point you start to build this false confidence, like we've spent too much time on this for it to not happen. There's too many people involved for this to not happen. happen, right? And I've learned really hard lessons over the past few years to never feel like that.

Right, right. Because— and that's kind of, as a leader, you can kind of say, what would a manager tell me to do right now?

Exactly.

Yeah, you've been like that one person, oh, it's going to happen, but he's not introducing you to other people. He's not asking for an updated proposal. He's not asking about new releases. There's no—

There's buying signals, but are there— but are there buying habits? Like, if he's— if you— if you're only talking with one person, red flag. If you're not getting introduced to other decision makers, red flag. But I think, I think that the nature of enterprise sales is, is— I like the old Reagan adage of trust but verify. Trust what your client says, but verify it. You know, there are a lot of people out there who will say never trust what your client says, believe no words that they say. And that's a bit of a pessimistic view. Most people, I believe, are inherently good. It's just that they're put in some awkward positions. So if somebody says something to you that's promising, Trust it, but verify it. And if that means verifying it by talking to other people at the org or sending a confirmation email or setting another call, whatever it is, just take the time to do that.

Yeah, cool. Hey, Jon, I really appreciate your time today. Where can people go to connect and follow you?

I'm available on LinkedIn, Jon Eric Silverman, J-O-N, and you can find me, you can find me there.

Hope you enjoyed that interview.

What a great guy. What's really nice to hear when you, you talk to great salespeople is that they're not selfish jerks, that they're very nice people. And they have success because they understand other people. And they don't assume they understand what other people are going through. That's kind of empathy. That know-it-all type, that's the opposite. of empathy. And we have to catch ourselves. It's not a binary skill. It's a spectrum. And we're all on the spectrum, aren't we? So we have to kind of take a step back and ask ourselves, you know, what are other people going through? What are our clients going through? Now, I did a poll on LinkedIn about why committed deals don't close. Those forecasts at the most likely But they don't close. And when I talk to senior sales leaders, it's, it's not like 10% don't close. It's like 3/4, half don't close. What does that tell you? Does it tell you that maybe the salespeople are optimistic, the manager's optimistic, the customer's optimistic? Uh, but we've been doing this for a while. We should know how long certain things take, shouldn't we? Or we don't know how to create urgency, sustain urgency. One of the things that people get out of Winning the Complex Sale is how to add direction, momentum, and control to a deal. Now think, those aren't just nice things to have. They're must things that you have to have in a deal for it to close. You have to know what direction to take it. You have to keep it moving, and you have to have some control over it, anticipating the traps that you naturally will fall into. It is an unnatural act for a company, a large company, to spend a large amount of money. I'm not talking about renewals or add-ons or some more licenses. Those are easier, that the trail's already been, uh, well beaten down. But a lot of us are selling new stuff into new customers, and that is very hard. That's the hardest. And especially when they don't have all the paperwork established, the trust established, the social proof already established. You need to learn how to do that. And that's what you get out of winning the complex sale. Now, the other point I wanted to make was I was looking through, you know, some people I've known my whole career, and you look at them on LinkedIn. Some have had great success, but most of them, it's kind of more of the same. Now, what's more of the same? Well, just watch like Back to the Future, the movie, where you see people just— they kind of just age. They don't really grow or evolve. They're just older. And if that's okay, if that's what you want, that's fine. I'm not saying there's anything wrong with it. But if you don't want that, if you want to grow, if you want to make more money, if you want to have a better lifestyle, then you have to do something different. That's why I always ask the question about what were some of the epiphanies And your career. And, you know, I try and dig down because the work harder one, that's the first one everyone tries. We all do it in our early career, in our 20s.

We get out of college.

We hopefully, we grind a little bit. And that's okay. We need it. It's practice. But it doesn't scale. You know, you don't find many 60-year-old grinders because they're probably dead. They're probably burnt out.

They're in rehab.

Um, because as a human being, we're flesh and bone, so grinding, uh, tends to not last very long. You tend to get burnt out, uh, and you see a lot of that in sales. There's a whole bunch of stuff out there about mental health and sales because they tried the solely grinding it, because that doesn't scale. It works for a short period of time. And then bad things happen. So you have to start working smarter, and you have to start doing smarter things. Now, the people that I did see have enormous success, there were pivot points, escape velocity, points of tipping— tipping being, you know, that there was a pressure and then all of a sudden success. Now, Here are some of the elements of it, and this is kind of career advice, but also, you know, knowing how and developing your skills and being open to becoming better is critical. A lot of people stay in that know-it-all B-player trap the whole life, and they tend to go in that downward spiral. They go from an A job to a B job to a B- to a C+ to a C to a C-. And all of a sudden they're out of work or they're doing— selling real estate on the side or whatever, trying to just pay the bills. The other people tend to find an opportunity, tend to be at the right place at the right time, kind of serendipity. Some would say luck. Some would just say, you know, preparation meets opportunity, whatever. The point is you do it. And if you listen to Malcolm Gladwell's book Outliers, his premise is that people who hit something at the right time with their 10,000 hours of skill and practice— it was right preparation, opportunity, boom. Now in sales, what I've seen is a couple of things, that the people who have done the best is they develop their skills, but then they got into the, the right industry at the right time, in the right company at the right time, with the right manager at the right time. Now, that's hard to do because how do you know it's right? Because by the time it's obvious that it's right, it's too late. What you have to do is find it early. You know, I think when I talk with reps, the best advice I come up with is find a great sales leader. Look on LinkedIn today. You can find it. It doesn't have to be just word of mouth. Listen to the Sales Leadership Show. Listen to the B2B Revenue Leadership Show. There's some great leaders on there. And if they're a great leader in a great industry at a great company, I would do anything I can work for them, with them.

Why?

Because if they're a climber as well, meaning that they want to go from a first-line manager, second-line manager, VP, CRO, then they want to take great people with them. They typically will only take people that they have worked with before, known players. Why does this work? Because it's too hard to try and find The right industry, the right company, the right— all of that is a judgment call. And you might get it right, or you might be too early, or you might be too late. And if you're too early, you struggle and it looks like it's your fault. If it's too late, quotas are oversigned, territories are too narrow, and if the manager doesn't already have faith in you, It'll assume that you're the problem, not the territory or the comp plan or the, the timing. So getting that right is critical. So if you're early in your career, I would look for first skill, because if you get that opportunity and you don't perform, then they're going to assume it's you, and it probably is you. But so once you have the skill Every great manager wants to keep you. Now, I did a video that I posted on LinkedIn, When the Top Sales Rep Quits. Now, I can just tell by the people who— how they responded. A great leader will do anything they can to keep the top performers because they know Price's Law. I did a video on Price's Law. Price's Law states that Half of the revenue will come from the square root of the number of reps. It's, it's like 80/20 but hyper-focused. And this is a, a natural recurring numeric equation in nature. You can fight it all you want. Check it out. It's, it's real. I didn't make it up. My point is that terrible managers want everything to be equal, meaning that they assume that every rep given the right opportunity will come out equal. Well, that's not nature. That's not a performance. That's a factory. Sales is a creative process. It's an intellectual process. It's an empathetic process. And this takes skill. And from those answers, there was a lot of managers— Oh, you got to have a deep bench of skill. Yeah, you should, but you don't let the best rep leave because guess where they go? Your competition. So now you just trained your competition. So you have a nice deep bench and you're the spring training company for your better competitor who's willing to pay for more talent. And this is something that only the best managers get, the top 5-10%. The admins, the morons, the bookkeepers, they just count the numbers. Here's how you tell. If they say they're data-driven, run for the hills. That's the sign that they don't understand sales because people love to hide behind dashboards and spreadsheets. Those are not leaders. Those are administrators. Run for the hills. Great sales leaders will look you in the eye and they won't admit that they understand how the game's played, but you can tell. And I've— you gotta watch the Sales Leadership Show because don't— even if you don't want to be a leader, you've got to be able to identify what a great sales leader is. Because if you get that manager, they're not going to stop when they're 30. 40, 50. They're going to go be a CEO somewhere, and they're going to take you with them. Get on the spaceship. And I always use this analogy: do you think the bat boy on the Yankees is any better than the bat boy on the Pirates, or the worst team in the league? No, they're a bat boy. Now, a player— yes, it is different.

You know, the pitchers are better on the Yankees, but they're paid more.

They recruit. My point is, get on the right team. Get in the right game because that is the ship that's going to the moon, going to where you want to go. You can be the biggest fish in a small pond, and if you just want to sunset your career, that's one strategy. But if you really want to go places, You've got to delegate a lot of that judgment skill to people who have better judgment. And the people who have better judgment are people who have already had success. Follow them and see how they treat reps. Because what you'll see is the same reps have gone from company to company like a pod where there's the leader and they bring the other people with them once they either burn out at another company or they're making too much money or something changes or there's a hotter thing. So this is gold advice. Take it at your own risk. We'll see you next time. Do me a favor, if you see my content fly by on LinkedIn, give it a like, comment, or share. So tell somebody about the podcast. Make sure you're checking out the whole network of them— Sales Questions, Brutally Honest Answers, That Sales Leadership Show, and the B2B Revenue Leadership Show. We'll see you next time.

Better, and especially post-COVID, you got to be very creative in healthcare, that's for sure.

Yeah, and you know, for people who are wondering if it's right for them, What would you tell them?

Yeah, I mean, I think you, you kind of need to get over your own ego a little bit. I mean, a lot of people think they're really, really good at sales and they probably are in some rights, but at the same time, like, I think you've mentioned it before, like professionals in whatever industry or athletics, whatever, you know, they're always getting better, they're practicing, they're continuing to improve. And, you know, I know beforehand I didn't necessarily think of sales like that as much, but kind of taking your course and doing that. Like, even if I'm ranked at, you know, the very top 1%, I really should be doing stuff to get better. And of course, a lot of companies will provide great stuff, but you really kind of need stuff outside of work, whether that be mentors or classes like yourself. So yeah, I think regardless of how good you've been doing, I think you don't want to get complacent and you want to keep getting better. It's just my opinion.

And You know, as far as, you know, getting better, do you see it as kind of a destination or a journey?

No, it's definitely a journey because I think most people in sales are competitive and, you know, even though that once they win a deal, they want to keep moving forward. So I don't see it as a final destination. I feel like it's something really you should be doing throughout your career, I guess, until you retire, hopefully sooner than later when you retire. Yeah, I think no matter if you're a sales rep or an executive vice president, you should be doing some type of coaching or training. And this kind of— I was doing a fair amount of stuff, but it was more company-driven things in the past. So I think expanding outside of that— I mean, nothing wrong with doing it within your company too, but expanding outside of that and getting different opinions, I feel like is a good thing, perspectives.

And how much time per week did it take you?

Yeah, I had certain moments where I was binging some of your content quite a bit. The actual courses, like, I wanted to be sitting down, you know, at home, able to write down notes and put stuff in Word documents, just kind of how I was doing it. So I would say I probably knocked out the Complex Sale course in 6 weeks or so. Um, I went after it pretty good. And then throughout that and afterwards, I would, you know, listen to the one-on-ones. I would listen to your every 2-week calls, kind of the open sessions. And I binge that a lot when I'm driving because I travel a lot for work. So I listen to those quite often and I don't necessarily have to take notes on it, but it's just good to get those real-life examples from other people. But yeah, the course took about 6 weeks or so, but that was just the pace I did it at. I mean, the nice thing about it is that you can can do it at your own pace, you know, throughout, you know, even a 12-month period, I guess, if you want to.

So.