The sales rep career path

Posted October 4, 2017

By Serena Miller

Editor, Sales Best Practices at Outreach

How an SDR can progress through the various stages of their career.

Mark Kosoglow:                  Good morning. Mark Kosoglow here, VP of Sales at Outreach.

Jacco :                                       And I'm Jacco van der Kooij, founder of Winning by Design.

Mark Kosoglow:                  Hey, we're going to talk this morning about the sales rep career path and how an SDR can progress throughout the different stages of their career as they're taking on, in my times, their first job, Jacco. Right?

Jacco :                                       That's right. Many times they are at their first job. First or even second job because they got fired in the first job for no reason that had to do anything with them.

Mark Kosoglow:                  Who's firing people for no reason? That doesn't even make sense.

Jacco :                                       That does make sense here in the Bay area where people get fired because somebody decided on a whim that they needed to change their sales organization.

Mark Kosoglow:                  Yeah, I hear about that all the time, obviously. Why can't people settle down? Why can't people say, "Hey, we're going to double down on SDRs and make sure that they're a valuable part of our organization."

Jacco :                                       I think that the big disconnect there is the misunderstanding about what SDRs do and how you can make them most effective. And I think that, again, that does not have to necessarily to do with the SDRs, but it has to do with the presumption that companies are bringing in SDRs with and trying to get them to do what they think they should be doing.

Mark Kosoglow:                  So the issue isn't necessarily the SDR, it's just the leadership's handling of the SDRs they bring in. What is a big problem that you think that they have around that?

Jacco :                                       For me, the biggest problem is, first and foremost, a misunderstanding how critical that role is. Because if you don't understand how critical the role is, then anything else doesn't matter. And so, to us, we often treat it as if it's a mail room function, that's traditional. Or in the end it is what every part, we are doing forces week, where most companies struggle with the most, which is generating leads, developing leads.

                                                      That person, that role, is in charge, or is a key function, of that. And so, to me, that is a really key role to a company's growth.

Mark Kosoglow:                  Yeah, at Outreach we really believe that maybe, next to developers, SDRs are the most key role in the entire organization. We call them the heartbeat of the entire company. And we also like to say that if an SDR sneezes then the entire company gets cancer. That's how important it is for us that SDRs perform all the time.

Jacco :                                       I love it. I'm in full agreement with that. What I think is a big issue for me, or what I see after that, after we realize that this is a key role is how do we develop them to be the person that we want them to be?

                                                      At the onset, we're going to think about SDRs as actually quite of a junior sales force, priority, like you said in the first or second part of the career. I think at the end of this conversation I want to say to me SDRs can be a career path by themselves. You don't have to become an AE. And what we see nowadays is actually SDRs in their mid 30s, mid 40s who are just focusing on that role by themselves coming into play. And I think that, overall, the entire SDR profile will benefit from a more diversified age bracket, or age denomination, across that role.

Mark Kosoglow:                  I would totally agree. I really benefit every day. I have several very senior SDRs that are later in their sales careers that have come in. They've just decided, "Listen, I like being the tip of this spear. I like breaking through the door and get in the meeting. I don't want to handle all the stuff after that."

                                                      But what about those young one? Those young guys come in, there's a word that floats around there, entitlement, that they need to have a career path, they need to have a flow to what's going on next, they need to have, like in a game, they need to have the next level they're about to achieve. Tell me a little bit about that because I have some opinions.

Jacco :                                       Well, since you have some opinions, why don't you start? Layer it up.

Mark Kosoglow:                  All right, so this is my opinion. I started my career as a sales guy in the field and my career path was if you do well today you can continue to work here tomorrow. I had no idea how I was going to become a senior sales rep, a senior accountant sales rep, I had no idea how I was going to become a sales manager. My focus was solely on doing my job and learning my craft to the best of my ability and then letting my performance elevate me in the organization.

                                                      So that's my thought, is listen, SDRs have a very critical role, they can really over-perform, they can shine, they can show their value to the organization. And that should dictate where they go next, no necessarily coming in and saying, "Hey, what's my career path and what do I need to do next to go to the next level?"

Jacco :                                       Hard work definitely matters, however, times have changed to some and we have to move with the times. I can't go back and say, "Well, you know, when I grew up in the '70s and '80s this is how we did it, let's do it again today." That's not how it works.

Mark Kosoglow:                  I didn't grow up in the '70s and '80s.

Jacco :                                       As my hairline indicates, I have. For me, we have to adjust to the times. And one of the key things that I find that we have to apply to people in the first and the second part of their jobs, we have to give them forms of micro-promotions. That is not in order to promote them in order to a senior director role after six months or nine months. That's not what they're asking for. That's not what we need to be doing.

                                                      What we need to be doing is giving them a path that they can go, "Okay, if I do it after three months, what is next?" Okay, after three months you're moving from inbound to outbound. "After doing three months outbound, what's next?" Then, I'm moving to outbound, using the Outreach tool. I'm going to get a new tool, I'm going to go-

Mark Kosoglow:                  Let me stop you for a second. It takes me 18 months in any role I've ever had to figure out what I don't even know I need to know. They're never given a chance to actually learn how to do their craft because they're so busy up-leveling to the next thing. When do you get to learn what you actually do?

Jacco :                                       As my son plays Call of Duty, if you play any game, you don't get stuck on one level for 18 months, keep playing. Keep working hard at it, you'll get it one time. I think that there's ... Obviously, you need to get a certain skillset, but you need to make the promotions, hence we call them micro-promotions, in such a way that in the three months you need to be able to gather the skillsets that are required in those three months.

                                                      Here's the opposite point. If you are an SDR for nine months and there's a new SDR coming, a brand new one, a brand new role, excited, and that person comes in at the exact same level where you are after 9 to 12 months, you're going to go, "Look, I just worked my butt off 9 to 12 months and I'm still at the same level that they are?" That's right. Now again, I don't want you to jump like, "Oh my God, he's already Director, Senior Director." And I think that's what we're doing today, and that is a mistake.

                                                      I think what you're saying is, "Okay, you go to SDR2 level, SDR3 level, so that you know that you're making progress." And then with every step we're able to give you new techniques, new tools, new whatever is needed in order to make you work on that level.

                                                      As long as we think of that progression as helpful to the job that they need to be doing so that we slowly but surely set them up for a career, and not just working on a manufacturing line for 9 to 12 months, and after that, "Thank you very much, you're good to go."

Mark Kosoglow:                  I went to Penn State. Penn State is known for HDFS, so they're one of the best HDFS schools!

Jacco :                                       What the heck is HDFS?

Mark Kosoglow:                  That's Human Development and Family Studies. All right?

Jacco :                                       Okay.

Mark Kosoglow:                  This is what I ... I took HDFS classes at college and I'm pretty much an expert now. This is what I'm going to tell you. Do you think that millennials look at their parents, stuck in a job for years with no way to grow up, and they say, "That's not going to happen to me." And they're forcing a theology or a methodology onto employers to say, "That's not going to happen to me."

Jacco :                                       I can't speak about that because that's beyond my skill level.

Mark Kosoglow:                  You should have gone to Penn State.

Jacco :                                       I should have gone to Penn State. Here's what I can say. In today's world of rapid change, if you're stuck, if you stand at the bus stop and there's no two buses coming then you're stuck. If you're stuck at a level in the elevator, and the elevator stops at four, and you're waiting five minutes, you're getting out or you're taking the stairs.

                                                      I believe the same thing. If you're stuck in a career and it's not going anywhere, and you're doing that for six months, nine months, you're moving on because this company ain't moving on with me, or ain't moving me on. I think that that is ... Whether that is a form of entitlement, I don't know. I think it's just a form of today's world. We're moving faster. And I think that that role, particularly, it is meant to be a fast moving role.

                                                      Now, what I don't want that role to be is that we're putting these people early on in their career in an environment too soon, which is what we see all the time. Now I have an early person in the career who has done barely one job right, now he's suddenly managing a team of six, and now having a one eye leading the blind.

Mark Kosoglow:                  That's not fair.

Jacco :                                       That's not fair today, man. Then they fail and then the company said, "Oh, fail." And then they have nowhere to go from that point forward. So I don't think that that is right either. So I think we, in particularly as an industry, as an industry that is heavily engaged in you folks with the tools that you have made, that are heavily engaged, they have young people early on in their career, it is our responsibility to get them on the right track. And guess what? Who will financially benefit from that?

Mark Kosoglow:                  The company, of course.

Jacco :                                       The companies will benefit. I think, and this is where I often find, is the tools that, for example, you have created over at Outreach. They match very well with that younger generation. It's very fast, a very automated processes, certain automated processes that you can do. It's very intuitive to them, it's very, as they say, part of the online generation and those who have become native in that. That's why, also, that you can leverage that.

Mark Kosoglow:                  Let me ask you this. This idea of being stuck, I had the same job for seven years, my first real job out of college, I never felt stuck because I was constantly getting better at what I did. Because my title never changed didn't make me feel like I didn't get stuck. Because my responsibilities didn't change didn't make me feel like I got stuck.

                                                      What made me feel like I got stuck was I outgrew the patch that I was given and I decided I didn't want to manage accounts anymore, I wanted to manage people. And so I worked towards that.

                                                      I think we really need to help SDRs understand, you're not stuck because you do SDR work for a year or two years or three years. You're only stuck if you quit growing as a person, if you quit acquiring the skills that you need to advance your career. That's what makes you stuck.

Jacco :                                       Practical story. What gets us in this mess is when a VP of Sales who heads up AEs and SDRs stands up in front of a classroom where there's 60 new SDRs being trained for the job, and where that VP of Sales says, "Some of you will be so lucky and so good that you'll end up being an AE." Which means that we expect only the good SDRs to become AEs. I think they are two different jobs and we should treat them differently. A Senior SDR is as senior as a Senior AE. Different roles, different responsibilities. There's no alpha, there's no Batman and Robin, there's no alpha and a beta, that's not what this is about.

                                                      SDR roles are very senior roles. Those who can get meetings with CXOs at large companies should be treated the same way as those people that can close reasonable deals.

Mark Kosoglow:                  I hear you. I totally believe that. All right, let's leave everybody with something. What is something that if you were talking to a sales leader that you would really want them to understand if they're struggling with millennials, entitlement, career path and all that kind of stuff, what would you really want them to understand?

Jacco :                                       I think that the top thing that we want to do, if you're a sales leader, is training, communication, and make sure to do lots of practice. Here's a couple of things that you can do. Start a book club. Every Friday you need to read a book or a section or watch a TED video, whatever it is, write your blog article, and you need to discuss it. Help these people get educated.

                                                      I think that lots of education is being overlooked. You may not always be able to afford a trainer if you have two or three SDRs, but at least start reading blog posts as a group, and then start discussing what are the pros and the cons. There's lots of good blog post writers these days out there, a lot of content really available.

Mark Kosoglow:                  My thought is I would say, like Jacco said just a minute ago, set the expectations, like, "This is your job, this is what you're going to do, this might be how long you're going to do it." But set the expectations so that we're not trying to advance you to the next stop, what we're trying to do is advance your skills that opens other doors for you in the company.

                                                      So make sure that the expectations of your SDRs when they're coming in is really defined. For us at Outreach, what we do is we say, "Listen, when you learn this job, when you master this job, when you can have great conversations that drive results on a consistent basis, the rest of the company will open up to you. Until then, let's work on making you as good as you can be at the role that you're in."

Jacco :                                       That's right, but actually what I like a lot about that is if you give a person the opportunity to confident in the role that they're doing then that gives them all the needed tools to move onto the next level. So I really like that.

Mark Kosoglow:                  Hey, join us at booth 1920 today down at Dreamforce. We have Gene McNaughton down there. He's doing the Sales Gym.

Jacco :                                       Jean.

Mark Kosoglow:                  We'd love for you to take the Sales Gym Challenge. And let us show you what our followup is like on leads at Outreach compared to your followup. I guarantee you that you'll think our followup is spot on.

                                                      So, hey, we really want to see you down there today. Thanks again, Jacco. Another great morning.

Jacco :                                       Most welcome.

Mark Kosoglow:                  We'll see you soon.

Jacco :                                       See you. 


Read more

Discover the Sales Execution Platform
See how Outreach helps sellers close over 2 million opportunities every month.