
The Millennial Sales Podcast · 2019-03-29
Key moments - from our scoring
Substance score
31 / 100
Five dimensions, 20 points each
For sales reps who've moved beyond the learning-to-sell phase but aren't yet veteran performers, this episode provides a framework for compounding their early success into sustained growth. The hosts argue that midterm reps should shift from transactional selling to strategic selling by understanding how their products fit into broader customer ecosystems - which requires knowledge of adjacent products, competitive positioning, and industry shifts. They emphasize taking on informal leadership roles (mentoring new hires, running best-practices groups) to explore management fit while building credibility. A central insight is that consistent, repeatable sales processes - built by consuming sales content from podcasts, books, and trainers - separate promotable reps from lucky ones. The episode concludes with hard-won advice on mentorship: stop searching for one perfect mentor across multiple life domains, and instead build a board of directors in specific areas (career, finance, health, family). Crucially, the hosts stress that serious mentors and coaches cost money - success requires investment in training programs and paid advisory relationships, not free guidance from peers. This is essential listening for reps ready to professionalize their approach.
Midterm reps should focus on creating predictable results and developing themselves as leaders and students by learning adjacent products, taking on leadership roles, studying competitors, consuming sales content, and building a mentor board.
Learning adjacent products gives you perspective on how your solution fits into the customer's broader environment, enabling you to sell more strategically and understand the business case for your technology relative to surrounding tools.
You can only make that decision effectively when you're clear on your sales process and criteria for success; if a deal doesn't meet those criteria, you should trust your process and cut the rope to focus your limited time on higher-probability opportunities.
No - you should build a board of directors with multiple mentors in different domains (career, finance, health, relationships) rather than searching for one person who excels in all areas, which is unrealistic and sets you up for failure.
No; successful people invest hundreds of thousands of dollars annually in coaches, masterminds, and trainings, so you should expect to pay for serious mentorship rather than hope busy successful people will mentor you for free.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode delivers five broadly reasonable career-development points for mid-tenure reps, but nearly all of them are generic (consume content, find a mentor, learn competitors) and padded with filler, tangents, and meandering back-and-forth. The Einstein compounding-interest digression, poker analogy, and repeated affirmations ('yeah, for sure') eat airtime without adding substance.
every podcast you can listen to, every article by someone you trust that you can read every book on sales processes or, you know, uh, being successful in sales, there's a thousand of them. Read them all
you should be striving to create predictable results and hone your identity as a leader and a lifelong student
The 'compounding privilege' concept is a mildly interesting reframe of network-effects-of-success, but it is never developed rigorously. The 'board of directors' mentor advice is widely circulated in popular self-help and business circles, and most other points (learn competitors, build a repeatable sales process) are standard sales canon with no contrarian angle.
success is a pay to play game
don't set the expectations too high on who you're going to find that you want to mentor
The episode is a co-hosted conversation between two peers who appear to be practicing enterprise sales reps; no external guest is brought in and no credentials or track records are established for either host. One host references managing a very large account, suggesting some real-world experience, but neither speaker is positioned as a senior practitioner or demonstrated leader in the field.
my account is 146,000 employees. They've got over 6,000 applications. You can't attack all of that in the same way that you would attack a small company
I've got a lot of failed experiments when it comes to mentors
The episode contains a handful of concrete details - the 146,000-employee account with 6,000-plus applications and the microservices-vs-monolith shift - but these are anecdotal reference points rather than evidence tied to outcomes, metrics, or named companies. Most advice is delivered in abstract terms with no dollar figures, win rates, timelines, or named organisations.
my account is 146,000 employees. They've got over 6,000 applications
a lot of developers and our customers in IT are moving from this big old monolithic way of delivering applications to microservices
The co-host format produces largely leading, gentle prompts ('So talk to me a little bit about how this has gone for you') with no real pushback, challenge, or probing follow-up. Claims go unexamined, the hosts agree with each other throughout, and several exchanges are simply mutual affirmation rather than productive interrogation.
So talk to me a little bit about how this has gone for you
Yeah. And I think just quickly before that, we should define compounding privilege
Computed from the transcript - who did the talking, and the words that came up most.
Welcome back! In this episode, we continue our 3 part series on the Compounding Privilege in sales and discuss the Top 5 Things you should be doing as a “midterm” Technology Sales rep. We’ve loosely defined a midterm rep as an individual who has had some time in their seat, experienced some success and failure, and is geared to take the next strides in his or her sales career. E3. Top 5 Things to do as a "Midterm" Technology Sales Rep Charlie Lisk and Jay Jackson
Transcribed and scored by The B2B Podcast Index.
Speaker A: Foreign
Speaker B: m.
Speaker A: Hey, and welcome to the Millennial Sales Podcast. This is episode three. Again, we're continuing to talk about leveraging compounding privilege. But today, Jay, what are we going to focus on?
Speaker B: We're focusing on those who are part of the way into your tenure as a sales rep.
Speaker A: Yeah. At this point, you should be either overly cocky that you know what you're doing because you got lucky a few times, or maybe you're pretty good. Or maybe at this point, you still just feel like, how in the world could I been doing this for 18 months or two years and still not know what in the world's going on?
Speaker B: Yeah. And I think just quickly before that, we should define compounding privilege. Again, um, not quite the same as compounding interest. Although Einstein did say compounding interest was the greatest invention of mankind. You know that?
Speaker A: You know, I didn't know he said he who.
Speaker B: Obviously, he said he who understands it earns it, and he who doesn't pays it. So, anyways, can you define compounding, uh, privilege?
Speaker A: That's kind of like what they say about. Yeah, that's what they say about poker, though, right? Like, if you walk up, you're. And you're at the table and you don't know who the schmuck is, you're the.
Speaker B: Yeah, yeah.
Speaker A: Um, so, yeah, so the compounding privilege is a lot like, uh, compounding financial principles. But in this case, we're talking about success and opportunities. So the concept of having access to good opportunities because of your current or past success, if you've been more successful in the past, especially in the sales world, where there's a little bit, uh, you know, it's a little bit more fluid in terms of what territory you get put in, what account you cover, whatever. But if you've been successful in the past and proven that you can make use of a good opportunity, your management will start to put you on the best opportunities because they need those things to execute. And that's the power. You do that, over time, you will find yourself in exponentially better places than other people because you've succeeded in the past.
Speaker B: And so what do we think that means, Tor, for a midterm sales rep, for somebody who's been in the seat for a little while, is pretty comfortable. What does compounding privilege mean for them?
Speaker A: Yeah. And so for the not so new sales reps, I like midterm, though. Uh, for the midterm sales reps, really, the top five things that you should be focusing on really fall under one theory. And that theory is that as a Midterm sales rep, you should create. You should be striving to create predictable results and hone your identity as a leader and a lifelong student. This is the focus of reps in this category that really breaks down into the top five things, kind uh, of sticking with this theme, right? So number one, learn about products outside your pillar or your product set. Not a lot of folks do that. Number two, assume leadership positions and become more well rounded. Right. And we'll talk about this in a minute. But if you're looking at going into management or anything like that, test some of those theories out first. But either way, you've got to build a brand as a leader. Number three, learn the competition really, really well. Right. For the first couple of years, you've just been trying to figure out what in the world it is that you sell. Now you got to figure out what everybody else sells. Okay? Number four, you've got to educate yourself more and more on the sales process through massive amounts of content. That content could be podcasts, could be books, could be, you know, one on ones with people, could be training programs, whatever. But you've got to get super educated on the sales process. We'll tell you why. And then number five, you got to find a mentor. And I've got a lot of failed experiments when it comes to mentors. So I'm kind of excited to share my faults as I approached that section of my career when I was a midterm sales rep to hopefully help everybody not make the same mistakes. So those are the top five, and
Speaker B: let's jump right into it. So as a midterm sales rep, I've already built a deep or deep enough knowledge into my own product set. I know what I'm doing, I know what I'm selling. And so now you're telling me to become more rounded. How does that help me?
Speaker A: Yeah, so learning. Because at this point in your career, you are selling more and more strategically, ideally. Right. A little bit less transactionally. Right. So bigger deal sizes, bigger accounts, possibly more deals, that type of thing. And to be able to do that stuff more effectively, you've got to learn and you've got to have perspective where your stuff fits into the big picture. Now, you can do that some through just your regular product training that you're going to get inevitably, uh, you know, from your own company, from your own pillar or whatever. But by going outside of that and actually talking to sales consultants from other lines of business, talking to sales reps from other lines of business, talking to people at the customer, that don't buy what you're selling. All of this stuff, Lynn's perspective as to what everybody's doing around you, which of course helps you figure out where you fit. And once you know where you fit, you can sell that.
Speaker B: Yeah, for sure. That's pretty natural. I mean, if you are able to understand your, uh, fit and your technology's fit, you're able to better sell it and you really build a business case that way. Right. Like if you just understand your technology and you don't understand the technology next to you, how can you talk about the business benefit that your technology has for the other technologies or the surrounding technologies?
Speaker A: Yeah, and I mean, and this is, and you know, through the first year or so of your career, you should be also focusing on, you should be exposed to how your company's telling you to learn your customer's business, learn how they make money, learn these things. And these are, you know, extremely important pieces of stuff that you should be doing at that, that juncture. Right. This is kind of an extension of that. This is 2.0 of that.
Speaker B: Yeah.
Speaker A: Right. So if you can, uh, you know, again, not just it's taking a less self centered approach to the sales cycle, which ultimately is just, it's going to help you become a better salesperson because you can have that conversation and know where you fit. And then frankly too, as you're listening to conversations, you can just participate more, be seen as having more knowledge, more value. Uh, so this is one surefire way to do that. Learn products outside your own pillar or your own product set. Get out there.
Speaker B: Yeah. Number two, the next one, assume leadership positions to become more well rounded. And that can mean just taking on a bigger role, right?
Speaker A: Yeah, yeah, taking on a bigger role. So here's some, some, you know, actual examples. Right. Taking on a, you know, mentorship, uh, you know, style role for any of the new folks that are just coming in. Remember that person you were two years ago. You know, take on some kind of official capacity and helping those people out. Do some type of mentor program with them, meet once a week, you know, help them with their deals or their strategies or whatever. Um, you know, it could also mean, you know, coming up with some kind of best practices group for your own team or your own sales floor where you go around and actually figure out what are all the best things that everyone's doing. Let me collect those into one place and we'll share them through a newsletter or through a call every two weeks or whatever. Right. Taking on more responsibility and exploring who you are. And who you are not as a leader only helps you really define and figure out moving forward, what kind of roles do I want? Do I want to go into management? Do I want to stay an individual contributor? Do I want, uh, to be a VP or a CEO one day? Do I want to go into training? Like, you've got to explore some of those things. And it just so happens that if you do that, through taking on and seeking out more leadership positions at this stage in your career, you're not only going to get the brand and the recognition and the adoration of your management for doing it, you'll also find out a lot more about where you want to go in the near term. And as you figure out who you are through these, you know, explorations.
Speaker B: Yeah. And that's the ability to lead. You lead in your position that you currently have. You lead from the back, right?
Speaker A: Yes. Yeah. There's a. You know, it's. I. I don't want to say what kind of book it is, good or bad book. I haven't actually finished it. It hadn't kept me that long to do it. But there is a book out there. He's actually by a preacher. I think he's Dallas or North Carolina or something. But it's called, uh, leading when you're not in charge. And it's that same concept. Right. Leadership, um, is not something that you're granted. Right. I mean, of course, there are people that outrank other people, but that's from a management perspective. Leadership can come from anywhere.
Speaker B: Yeah.
Speaker A: And what you'll find is you are going to be more impactful in your accounts. If you can be a leader, no matter what position you're in, it'll always have limits. It'll always have caps. But you. But you've got to push all the way to where you find those realistic caps and then own everything underneath it.
Speaker B: Yeah.
Speaker A: Super important.
Speaker B: For sure. All right, let's move forward. The third is learning and knowing your competition really well. I like this one a lot.
Speaker A: Oh, uh, yeah. Why do you like this? Oh, yeah. You're like the master of this.
Speaker B: I think it's incredibly important. I think your job, especially after you've spent some time and you're comfortable, you should ferociously study your competition. This will not only help you, uh, and it'll help you sound like you know what you're talking about, but I think you just can't be wrong. Right. You have to do the homework, you have to put in the efforts, and you should know exactly what's going on. At your biggest competitor.
Speaker A: So give me an example and I'll give you an example of how I, how I use this. But yours is actually a little bit different. You have more of a, uh, technology focus, whereas mine, and it's probably just because my role, but, but my focus is a little bit more what is our strategy going to be based on where we fit with our competition. So talk about some of the stuff that you're doing because you're doing a lot of training with some of your fellow reps around some of your biggest competitors right now. What is that?
Speaker B: Yeah, we've done a couple training exercises on studying exactly what if I was a sales rep at my competitor, I want to know exactly what this rep would sell to the same individual that I'm talking to. So that puts me in a mindset and equipped me with the knowledge that I need to sell better against my competition. Tell me about what you are doing from a, I think a higher level or more of a business approach.
Speaker A: Yeah, so mine, I, you know, my account set is essentially, you know, one giant account. Right. So I've got a kind of an interesting focus, um, to where I've got to look at their business in its entirety. They've been a customer for a very long time. They're, there's of course the switch right now where a lot of developers and our customers in IT are moving from this big old monolithic way of delivering applications to microservices. And it's changing the way that people make stuff. And of course in that there's a lot of new tools out there that change what people use to make stuff. And so my approach is to not only make sure that we remain a big part of our customers environments and IT strategy and product strategy with a certain type of, you know, strategy. Um, but then I also have to go look at all the stuff that people are doing moving forward and where our competition is starting to chip away at that. And we're not really in a ton of danger today. But I have to know where they're chipping away at us. To where two years, five years, ten years from now. Yeah, this is not going to be in our account. It's going to be their account and they're going to do it slowly. And if we don't recognize how they do that and how to combat that, then we're slowly going to find ourselves at a position on this thing and it's going to be too late by then. So my approach is, it's a little bit more of looking at, um, what they do and how they do it, just to see, um, you know, what's our strategy for this account going to be? Because they're not going to be able to communicate that across dozens of reps that are selling into my space.
Speaker B: And it's fully proactive. Right. Understanding your competition's proactive and knowing. I think mine is strengths focused and also knowing the weaknesses. But I mean, same for you is really being able to hone on, uh, where we need to be stronger or where we need to demonstrate more value to the sales cycle.
Speaker A: Yeah. And frankly for me, a lot of it is figuring out where I do and don't need to spend my time. You know, I don't sell into a massive amount of accounts where if I screw something up or they go with a competitor or whatever, uh, then I just, you know, it sucks. But I move on to the next one. Mine I have to figure out where is our highest probability of success within the account that I have. And to be able to do that, you've got to understand where you should and should not spend your time. I mean, my account is 146,000 employees. They've got over 6,000 applications. You can't attack all of that in the same way that you would attack a small company. Right. So I've got to be able to sort through all of that and say the 5,000 new apps that they're building, which of those workloads should I go after and which should I simply not? Because I've only got so much time, so many resources and I've got to be hyper focused.
Speaker B: Yeah.
Speaker A: And so that is aided by understanding what my competition is frankly better at. I should be like, yeah, take it. Yeah, uh, that one's yours. You know, we're not so good there. But these, these should be mine. Fight for those.
Speaker B: I think that leads us perfectly into the fourth one, which is understanding and knowing the sales process. And one part of knowing the sales process is being able to know when a, uh, sales over and know when you, you know where and when you should and shouldn't focus your time.
Speaker A: Yeah. You know it when a sale's over. I really like that. It's so funny too because if you look at the beginning of your career and you always hear like more experienced people say, well, there's customers you want, customers you don't want to, you know, and at the beginning of career, like, shit, I take any customer. Yeah. You know. Yeah, you know, and it's funny, it's like a real sign of, uh, you know, maturity and experience when you can look at it and say, no, that's not for us. I don't want that. Or, you know what? This one, we should cut the rope on this one and just move on. Right. Uh, that's a hard, hard choice to make. But you can only make that choice effectively if you're really climbing clear on what your sales process is, what your criteria for success are, and if it's just not meeting them, then you got to trust your process.
Speaker B: Yeah. And let's talk a little bit more about understanding and diving into the sales processes. These, this can be understanding different sales processes. This could be exposing yourself to the literature that's already out there. What do you have in mind when you think about learning and educating yourself on sales processes?
Speaker A: Yeah. So the way that we wrote this down is educate yourself more and more on the sales process through massive amounts of content. So what I mean by that is every podcast you can listen to, every article by someone you trust that you can read every book on sales processes or, you know, uh, being successful in sales, there's a thousand of them. Read them all, right? Because you're going to get something from all of them again, just like we did in the last episode with brand new reps, you really want to consume a lot of content to be able to figure out and craft what is my sales process, what is my style. But to do that, you've got to be able to pull from as many other people as you can. And really, uh, what it's really about is if you can create a repeatable, predictable sales process to where you're doing the same things in a process that works, you'll be able to then create predictable results.
Speaker B: Yeah.
Speaker A: As you get further in your career, management looks at rewards, promotes, uh, you know, cherishes consistent reps, people who blow it out one year and then bomb the next three quarters. There is. They may as well have not ever done well. Right. We all recognize that people can get lucky. What management really truly wants, it will set you apart from a lot of people in sales is to be able to perform consistently. But you can't perform consistently if you aren't consistently putting in the same amount of, uh, efforts through, uh, a, uh, defined sales process process to be able to create those predictable results. Right?
Speaker B: Yeah.
Speaker A: So having a sales process is as much about knowing where to spend your time, where not to spend your time, you know, by kind of having, having that education there and those criteria there. But it's really about being able to create predictable results that's going to set you apart from most of your peer reps who are hit and miss. Right. Those reps are dime a dozen. Right.
Speaker B: For sure.
Speaker A: For sure.
Speaker B: And let's move on to our last one. You left me a little excited thinking about this one, hearing about the successes and trials you've had with this, but the last one is finding a medic. So talk to me a little bit about how this has gone for you.
Speaker A: Look, I mean, here's the best advice I can give on this one. Don't do it like I did it. Right. And I suppose for, like, so many. So many things in life, that's usually a good place to start. Find someone who really screwed it up and then just don't do what they did. So here was the mistake I made, right, in trying to find a mentor is I looked for someone who had the marriage and was the father that I wanted to be. I looked for someone who was successful financially and had the investment strategy I believed in. I looked for someone who did well at work and took the path that I wanted to take. I looked at someone who, uh. Or I looked for somebody who, you know, was physically fit and made that a priority, made travel. Like, I basically defined myself in 30 years. Yeah, right, yeah. Like, the person I wanted to be. Um, and I looked for that person for, like, two years, and I got really frustrated when I couldn't find it. Um, because there's, you know, you in 30 years does not exist in another soul. That is not a thing. I wasn't, you know, I was creating these criteria in, like, these five different buckets that were very narrow and very strict, and then expecting to run across somebody in my tiny circle.
Speaker B: Yeah.
Speaker A: That was going to be able to check all those boxes. It was a ridiculous expectation. I didn't recognize it at the time. Um, but it really set me up for a lot of failure and a lot of lost time, you know. So what it really came down to was I didn't need to find one person with all those five, really, uh, strong buckets. I needed to find five people that, you know, could hit each bucket the way that I needed them to. Somebody to look up to for family and marriage, somebody to look up to for financial strategy and wealth, somebody to look up to for work success, physical success, travel, whatever. Yeah, right. So, first bit of advice, don't set the expectations too high on who you're going to find that you want to mentor. You have realistic expectations to say it's likely going to be multiple people. And if anybody's listening to this Saying, well, no shit, that makes sense. You're better off than I was, because I did not start out thinking, yeah.
Speaker B: Uh, and I think what we. What I learned and was taught was instead of finding a single mentor, if you do great, you got lucky. What's more likely and what can really help you is building yourself a board of directors to help guide you along your life and leading on your board when you have decisions that you need to make or things that come up in your life. So build that board of directors for yourself.
Speaker A: You're totally right. And that's a wonderful way to put it. I. I didn't get that guidance growing up, you know, and that's. That's one unfortunate. And a lot of people, uh, you know, find themselves in that place. In a lot of areas in life, you weren't taught, therefore, you don't know. Right. And that's the point of all this, you know? You know, seeking massive amounts of education through content or finding a mentor to help you with these things. Let this be your one mentor call that says, hey, there's no one mentor. It's a board of directors. Yeah. Right. So I'll save you a couple years of heartache, like what I have, uh, you know, to go out there and create that for yourself. Yeah.
Speaker B: Well, I think that just about wraps us up for this, uh, episode. Is there anything else you wanted to cover for the midterm sales rep?
Speaker A: There actually is. I want to make one more point on the mentor the mentor piece. Aside from creating the board, the people who you want to learn from won't do it for free. I have fought this concept for a long time, and, you know, when. And I. I again looked around for somebody that would just want to spend their time with me out of the goodness of their own heart. And it turns out that was the wrong approach, too. As I went to more business conferences, took more business trainings, got it exposed to the world of guys who were super successful in business. They all spend hundreds of thousands of dollars a year on their coaches, their masterminds, their trainings that they go and do, and the expectation that, uh, definitely I had. And I don't know, I'm sure there's a bunch of people out there that think this, that you should just be able to go to somebody and be like, hey, you want to feel good about yourself? Spend an hour with me every month and mentor me and teach me all the shit that, you know, the people that will do that are not the people that you should be seeking a mentorship from. Okay. That was one of the biggest lessons that I had to learn is success is a pay to play game. Whether it be in the trainings you take or the mentors you seek or the company you keep or the, uh, networking events that you go to, success is a pay to play game. So set the right expectations for yourself when you seek this board of directors. Not a one on one mentor. And just understand that that's something you're going to come up against if you don't have a ton to pour into it. Do what you can for now, but just, uh, I want you to have the right expectation that when you go in, you're seeking these people that you want to get advice from. Just know that the folks that will really hand it to you for free, unless it's like, been a family friend forever, and he really will do it just for you, but not for other people. You know, just make sure you're choosing wisely and have the right expectations going in.
Speaker B: And that just about wraps it up. Tune in for our next episode where we'll talk about the top five points that are important for veteran reps. And thanks for tuning in.
Speaker A: Perfect. Thanks, guys.
Speaker B: Sam,
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