


23 Sep 2026 · 13m · 6 chapters

How to tell if you’re in the right sales job, especially early vs later in your career; how to choose a sales leader, find your sales “fit,” and improve when you’re on an island without strong peer reps.
Gabriel (Montreal, Canada), a business development representative at small startups; early-career, curious about self-doubt and role/company fit; interested in strategy/rev ops more than phone-heavy appointment setting.
Early career you usually can’t know fit—take the offer, learn, and move on; later, prioritize the boss/leader over the company (right leader can mean up to ~20% higher income); “mimic top reps” is overplayed—benchmark fundamentals and learn via training/networking.
Jeb’s early job he hated and left quickly; leaders Mary Gardner and Bob Blackwell who shaped his success; golf analogy (can’t mimic Scotty Scheffler).
Written by AI. May contain mistakes.
Jeb discusses how to choose the right sales job early in your career.
“So tell me what's going on in your world.”
Highlighting the role of a good leader in sales success and career choices.
“OK, because there's real data behind this that when you work for the right sales leader, that you can see upwards to a 20 percent higher income than people who work for a poor leader.”
Exploring various sales roles and focusing on what makes you happy in your career.
“If you chase the company, you can get bad leaders.”
Discussing how to identify your strengths and career interests in sales.
“So this is the second sort of really early startup that I've worked at.”
Jeb emphasizes the importance of continuous learning and self-improvement in sales.
“and giving yourself a routed education, but where you are as a lone wolf in your organization, you're not going to find anything that you can emulate other than you got to make those things happen yourself.”
Learn about strategic choices when selecting a sales position.
“then maybe the next business you go to, choose a startup that's got more than one salesperson.”

Get the gist, explore an idea or ask about something said.
On Sales Gravy: Jeb Blount, what are the key points of this episode?
Automatic transcript. May contain errors.
0:00Find the vacation you're looking for in Missouri. Whether you're searching for this, wanting something like this. Oh, that's cute. Maybe up for something like this. Or just really, really need something more like this. You'll find the vacation you want in Missouri. Missouri, it's the getaway that gets you. Plan your fun at visitmo.com. This is the Sales Gravy Podcast. Hi, I'm Jeb Blunt, best-selling author, fanatical prospecting, objections, sales EQ, and inked, and I'm here to help you open more doors, close bigger deals, and rock your commission check. All right, next up on the show is Gabriel from Montreal, Canada.
0:50I love Montreal. I was up in Montreal last summer. So tell me what's going on in your world. Yeah, hey, Jeb, it's really great to meet you. Thank you for having me on. In my world, I'm currently a business development rep. I'm working at a really small startup right now. I've had this role for a few different companies so far. And I was just kind of curious. I'm still pretty early in my career for context. And I just had some questions around how you choose the right company, self-doubt, or am I making the right choice? Have you ever questioned if your position was for you? You know, sales is a job with ups and downs.
1:20In periods of downs, how do you deal with that and what strategies do you use to deal with that? The answer is all of the above. I've definitely been in situations where I've questioned, is it the right job for me? And I've been in situations where I knew it wasn't the right job for me and I had to get out. That was early on in my career. So the one thing about understanding or knowing if it's the right company for you and the right fit for you, almost always at the beginning of your career, you're not going to know that. And nor are you going to have as many choices. In a lot of cases, when you're entry level, you're just going to take what you can get.
1:51You're going to go interview with people. If you get multiple offers, you're going to make a decision. But usually the decision you're going to make is based on how they make you feel in the interview. Is the leader that you're interviewing with someone you'd want to work for? But you're not going to really know in your heart, is this the right sales job for me or the right role for me? And it wouldn't be fair to tell you or anyone else otherwise. So if you're at the beginning of your career, take what you can get, go in there with an open mind and go be the best you can possibly be at that job.
2:19But the likelihood is that it probably won't be the best fit for you. And that happened to me. Like at the beginning of my career, I had a couple of sales jobs. And in fact, just a couple of weeks ago, I was talking to one of my very first bosses who I'm still friends with, but I hated that job. I couldn't stand it. As soon as I could get something else, I left. But at least the experience taught me that that's not something that I wanted to do. Like I didn't want that particular role. Yeah, that's really interesting. I think I look at it the same way. Whereas even if it's not the right fit, that's still a valuable experience.
2:47And you're still like learning from that experience. Because if you narrow down what you don't want to do, then it leads you closer to what you do want to do. The other thing I would say is for everyone, if you're looking at changing careers or going to a different job, the deeper you get into your career, the more important it is for you to choose the right boss rather than the right company. OK, because there's real data behind this that when you work for the right sales leader, that you can see upwards to a 20 percent higher income than people who work for a poor leader. So in those cases, like let's say you go to your second or your third job, then you're interviewing the leader.
3:24And in those cases, one of the things I want to do is like part of the interview process. Can I go spend a day with one of your reps or can I go hang out on your sales floor for a few hours and just see how things are run here? Because as you get into like your second, third job, the quality of your leader is going to have such an impact on your growth and your development. And you want to work for a leader who is a good coach, someone who's going to invest in you, someone who actually cares about their people. But you're testing to see, are the people working for this leader, are they willing to run through a wall for them?
3:56Right. Because I look at my career and I even look at where I am today. And I can name Mary Gardner, one of my early leaders, Bob Blackwell, one of my early leaders. They were so instrumental to who I became. And I got lucky working for both of them. And neither one of them were like, I didn't walk in and think this is the job that I want for the rest of my life. You know, I wasn't thinking that. But because they were such good leaders, they made me phenomenally successful in that particular role. So let's go back to first with your entry level. You got to take what you can get and you get it and you learn from it.
4:30You go be the very best you can at that job, even if you hate it, and then move to the next thing. But as you start moving to the second and third part of your career, like the second and third jobs, focus on your leader, not so much the company. If you chase the company, you can get bad leaders. There's some really sexy jobs out there in sales that because they're sexy, everybody wants them. And when everybody wants a job, it's a lot easier to treat you badly or to have leaders that treat you badly. If you work for a company that's growing so fast that all the salespeople just keep getting promoted into leadership roles, you're probably going to end up with a lot of bad leaders because nobody's teaching them how to lead.
5:04Once you get to like that second or third job, now you're starting to get experience. And you start looking at the world and saying, okay, what really makes me happy? Where's my heart? And that's when you can start thinking about, okay, what type of role do I want? And the beautiful thing about sales is we have a tendency to look at sales as a one-dimensional job, but it's not. There's everything from being account manager to being like pure hunters to BDRs to account executives. There are roles where you do both of those things. There's enterprise and national accounts. There are roles of sales leaders.
5:37There's so much that you can do. Focus on that. And I would focus on that way more than I would focus on what I'm selling. I mean, there's a whole industrial complex out there that tells salespeople that you need to believe in what you sell. To some extent, true. I mean, it's helpful that you believe in what you sell. It's more helpful that you like selling, right? That you like the industry or like what you do. So for example, I sold a project for like 10 years that I just was not interested in. It didn't juice me. It didn't give me anything that was, I would even call motivation, but I loved the selling part.
6:10Like I loved solving the problems. I love the fact that I got to walk into all these different businesses that every single day was different and that it allowed me to get in and be a real consultant for them. The product I didn't care about, but I liked that selling process. And so I didn't leave because who cared about the product? It made me happy to be a problem solver. So that'd be my question for you. When you look at the world and you say, I'm just getting started in my career. I'm looking out at all the things that I can do. If you were to like list out the things that make you happy at work, what would they be?
7:06And that's why Jeb Senior and I and all of Sales Gravy trusts our Plod Notepen S. Try Plod and stay focused on the conversation while it handles all of your notes. Go to plod.ai forward slash Jeb. That's plod.ai forward slash Jeb and use code JEB to get 10 % off your purchase. So this is the second sort of really early startup that I've worked at. And I really enjoy, I guess, let's say like the strategy aspect more than I enjoy the actual how many people actually enjoy getting on the phone and making$100 a day. I'd find it much more interesting, a little bit of the rev ops aspect of it. Who are we going after?
7:42Why are we going after them? And sort of, you know, making a plan to go after them and executing on that, measuring the results from it, and then, you know, adapting to it. That's sort of the part that I'm really interested in. that interests me the most rather than, say, talking to people and diagnosing their problems. Does that make sense? It does. Where do you feel like that might fit from a career standpoint going forward? I don't really know 100 % enough. I think definitely I enjoy working in a smaller company or in a role where you do get to wear a lot of hats rather than just being specialized and doing one thing.
8:16So I'm not really sure kind of how that fits in, I guess. I love the fact that I woke up every day and every day was different. What I sold was boring, but how I sold was not boring. You like variety. You enjoy the wonky part of selling, right? So I do too. I love figuring out the strategy and going after it, but I also really like talking to people. Give me a list. And I banked through a hundred calls on a list and looking back and saying, I got this information. I opened these doors up. I was able to move these things forward. I like that because I'm a process-driven person, not necessarily a relationship-driven person.
8:51So I love putting all the pieces in place. If you look forward, maybe the place for you is in some sort of a rev ops or sales operations role where you master this at the ground level. You can look people in the eye and go, look, I can make$100 a day and set appointments all day long. I can do it better than anybody else in this team. Now, I don't want to do it. I don't like doing it. It makes me happy, right? But I can do it better than anybody else. What really makes me happy is figuring out how we're going to get there. So I love putting all those pieces together. There's a real role for that in small organizations that need that expertise to help them figure out the process of getting there.
9:31Now, one day you might be in the trenches with the sales team picking up the phone and dialing people. But the next day you might be taking a look at the entire digital footprint of the organization and figuring out exactly how you're going to go to market. And so if you think about it that way and said, this would make me really happy. That gives you the variety. It gives you strategy. It allows you to work for smaller organizations and it gives you an expertise that is everything is constantly changing. And it allows you also to get a foot into marketing as well, because then you're looking at demand gen as well as like your outbound strategy.
10:04I'm just throwing this out to you. That's awesome. But to get there, right, you've got to build this core ground level foundational expertise where you say, I am the best damn salesperson that any of these companies have. As a BDR, nobody's better than me. I'm good at this. I don't like doing it, but I'm freaking good at it. And then you start going, okay, three years away, I want to be doing this. Or like at your company now, you go, hey, I'll volunteer. I'll stay. I'll come in on Saturday. I'll stay late. I'll do whatever. But I want to get involved in a strategy piece of this. I want to help with this so you can get experience.
10:37You get to stay in the space, but you get to do the thing that makes you want to wake up every day and run into work. If that makes sense. Yeah, no, totally. That's really awesome. Related to kind of what you were mentioning before, what you're touching on a little bit before about your boss, your manager, choosing a good leader. A lot of sales advice for becoming a better salesperson is basically find the best rep and mimic what they're doing. I'm the only rep and there's guidance from leadership, but it's, I'm the only one really doing this day to day. My question is, in that case, what's the best way to improve or how do you benchmark yourself?
11:10How do you set the right goals? How do you improve when there's not really someone that's doing exactly that for more years than you? The mimic another rep is doing well is a little bit, I don't know, overplayed. Because in a lot of cases, if you see another rep who's doing really, really well, why they're doing really well right now has almost nothing to do with what got them to the dance in the first place. and they have a really hard time explaining it to you because what they're doing looks really easy. It'd be like, if you play golf, like how do I mimic Scotty Scheffler? You know, I can watch Scotty Scheffler play golf all day long.
11:41I cannot mimic this because what got Scotty Scheffler to the place he is right now, I didn't go through those steps. I would have to go back to being nine years old, right? And go learn how to play golf again. I mean, there's some credence to it, but it's not the best. The issue that you have is really hard is that you're on an island. So you've got a leadership team that pays you vague attention. They pay you some attention, but they're not like in there helping you. They're just telling you, go set more appointments. The best way that you can learn is like what you're doing right now. I mean, hopping on here is courageous.
12:10Call me up and ask me a question. You're reading Fanatical Prospecting, which is a really good book to read. This book right here, 90 Days to Level Up Your Sales Skills. This is like a daily devotional. So one day at a time, there's one lesson at a time and an exercise that goes with it. There's also QR codes on the exercise so you can get into our system and watch videos that are connected with this book. And this book is hot right now. People love it because it's just little lessons at a time. You can also develop networking groups. So locally, like find other people out there in your space.
12:40Like my son's a member of a running group, you know, so there's got to be a BDR group out there someplace that you can get connected to where you can actually see people face to face. And then like you can go to conferences like the Outbound Conference, which is a great conference to go to. So you can hang out and network with other reps. You can go to Sales Gravy University where we've got tons and tons of training opportunities for you there. listen to the Sales Gravy podcast and other podcasts. Like there's tons of other sales podcasts out there. My buddies, Mike Weinberg and Mark Hunter have podcasts.
13:09There's a lot of things that you can do to make yourself better. And the other thing I would tell you is get out of sales, like read other books that have nothing to do with sales that improve business acumen or improve your motivation. I just read a book called Chop Wood, Carry Water, which is a really good book and it's good for your heart. Think just continuous learning and giving yourself a routed education, but where you are as a lone wolf in your organization, you're not going to find anything that you can emulate other than you got to make those things happen yourself. The one thing that I would tell you, and that's why I would say fanatical prospecting, 90 days level at your sales skills, is the basic fundamentals of what you're doing are not going to change.
13:47And you master the basics and fundamentals, you're going to get the results that you're looking for. So do that first. And then as you grow in this business and you get to the point where they were going to add more people or it's time for you to go to the next business, then maybe the next business you go to, choose a startup that's got more than one salesperson. Okay, that's awesome. How do I get my hands on 90 days to level up? You get your hands on it by going to amazon.com and they will have it for you right there. Okay, awesome. Thank you, sir. I appreciate it. And stay in touch with me.
14:16Let me know how you're doing, okay? Thank you, John. I really appreciate it.
14:38We'll be right back.
How do you know if your sales role is right for you? And how do you get better when you're the only rep on the team with no one to learn from?
In this episode of Ask Jeb on the Sales Gravy Podcast, Jeb Blount answers two questions from Gabriel, an early-career business development rep in Montreal working at a small startup.
Jeb's advice: at the start of your career, you often have to take what you can get and be the best at it, even if it isn't the right fit. As you gain experience, stop chasing the right company and start choosing the right leader. And when there's no top performer to follow, master the fundamentals and build your own learning path.
What You'll Learn:
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Purchase Jeb Blount's new book: 90 Days to Level Up Your Sales Skills
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