In the wild world of sales, Sales Development Representatives (SDRs) are low on the totem pole when it comes to seniority – yet many sales teams would not be able to function without them.
The SDR role is known for its high churn rate, harsh rejections from leads, and difficult commission structures. Due to this, many leave the SDR role and never return to sales.
Few rarely make the climb from SDR to C-Suite but Jesse Gittler, who has successfully made the journey from Sales Development Rep to executive leadership, is ready to change that.
In this episode of Evolved Sales Live, host Jonathan Fischer sits down with Jesse to uncover the critical steps that lead to his success and discuss what current sales leaders can do to create effective promotional paths for their team.
Don't forget to follow us on LinkedIn for more engaging sales insights and discussions! Happy watching!
Meet Jesse:
After starting his sales career as an SDR, Jesse Gittler has advanced into leadership roles at several high-profile tech companies like Tebra, where he currently serves as the Director of Sales Development. Jesse specializes in Client Relationship Management, Sales/Business Development, Effective Communication, Negotiation, Lead Generation/Conversion, Prospecting, IT services and support, hardware, and software sales.
Check out the transcription of this webinar episode below!
Jonathan Fischer 0:03
Welcome back. I'm Jonathan Fisher. In the world of b2b sales, companies all around the world depend on 1000s of very hardworking people known as SDRs. sales development representatives. It's always been a tough job and recent years have only made it even harder. If you're an SDR yourself, what steps can you take to help create a longer lasting, more satisfying career for yourself? If you manage STRS? How can you help your team reach and maintain peak performance? Well, our guest today is going to help us with that. Starting out as an SDR himself, Jesse Gettler has advanced into leadership roles in several high profile tech companies, including Tabora, where he currently serves as the director of sales development. Jesse also generously shares his insights and wisdom with others who are trying to be effective in their leadership of their SDR teams, and is here to do that for us today as our guest, Jessie, welcome to the show.
Jesse Gittler 0:58
Thank you. Happy to be here. Thank you.
Jonathan Fischer 1:01
We're happy to have you. Yeah. So you're a rock star. Jesse, you've done a lot of cool stuff. Can you tell our guests our audience rather a little bit more about what you do every day in your role at Deborah?
Jesse Gittler 1:11
Yeah, sure. So my job is director of sales development at Tempora. Ultimately, I oversee a board of STRS and have around 30. And I have three managers that roll up to me now. It's interesting question, you know, what you do or what the goal is of my job and as a director, because this is something I like to talk about a lot, which I think people get kind of confused by or when I'm teaching or coaching, I always try to break it down into its simplest forms. It starts with what is the actual goal of your job, right? And we could talk about it at like for the SDR for example, the goal. The job of an SDR is is people would say to book meetings, but it's not it's really to gauge curiosity. That's, that's really what you're trying to do. You can't make someone take a meeting. When you're closing business, people would say, what's the job of a closer you'd say, to sell to bring in revenue, essentially, you have no choice or no control, if they're going to buy from you, you just need to get them to want what you have. Right? You need to make them make a decision, ultimately, as a manager, and this is the big one that I think most if there are any managers listening, definitely, definitely whenever you get pulled around, and up and under, and you're all over the place. And the ultimate goal is to make your people better. That's what you need to revise or come back to every single time you're overwhelmed with the marketing meetings and ops meetings and hiring and all that. And as a director, what I do every day is ultimately to make my org better, right? Trying to level up my managers put process in play, get creative with outreach, and things of that nature. So I thought it was a cool question. I always like to try to bring it back to its simplest form of fiber get a little bit, you know?
Jonathan Fischer 2:46
Well, I love that because I think how you define success is really a critical key and maybe one of the areas where people missed the mark on this front. And I like to start the conversation there on our topic. Today, we want to discuss how an SDR can advance into the C suite. He could probably take that different ways. But the reality is a lot of leaders do start off in that original Chair of it's kind of a grind, right? It's hard work, it's a good place to prove out your work ethic gained some really good usable skills. I don't want us to question you can answer them in either order you like one is you've been at it for a little while you're younger guy, but you've been at it for a minute. How have you seen it change, especially coming out of the COVID? Era? Let's call it and where do you see people today still missing the mark as STRS? And as managers of STRS?
Jesse Gittler 3:36
Yeah, definitely. So, you know, I'll tell you what, when we went remote, originally, like in this was, I'm an in person, guy, I'm an office guy. I'm like, Let's go Let's rally like, and I work from home wasn't even a thing. Like where I was from, it just wasn't a thing for STRS at all, I can be laughed at it. Like if you need to work from home, like you better tell me what you were going to do when you check in. And, you know, like, it wasn't something that was like, I'm gonna work from tomorrow. And then, you know, obviously, like everybody else, they told us we're gonna try to work from home on Friday, the whole company never went back. And I remember the first couple of weeks after that. I told my boss at the time, I said, I'm going back to closing like, I'm not, I don't know, like, like, seriously, like, I don't know if I could do this like. So I think where it changed from that is you know, it makes a hard job harder, right? Because now you don't get to go and show up to a place where everyone's in it together doing the same thing get to rally and lean and also learn a lot by osmosis. Like, which makes the manager's job a lot harder because you're picking up so many things by just listening to people around you. And you're gaining a lot more confidence faster by putting yourself out there amongst your peers. You're learning more social skills like I think this is not talked about enough to like we're remote now we come in here. I mean, I'm in this. I'm in the seat for you I could week and I won't see anybody essentially, like I'm just here. And then I do you know what I got to do after work but like, you forget that like, you know you're working or used to work with with people or not, you know, it's just, it's, I think people get burnt out faster now, because they don't have enough of that support in person for people to lean on. What was the second part
Jonathan Fischer 5:25
of the question? Well, so how how you seen things change was the first part and this, I think you're kind of already segwaying into how are people missing MISSING THE MARK today? Even post COVID? Like, maybe they haven't made the correct moves to adjust?
Jesse Gittler 5:39
Yeah, I think like anything in life perspective is, you know, cliche. You know, nowadays, everyone's talks about it. But it really is so important as an SDR. And when you first start this type of career, I actually got off the phone with somebody today that I was interviewing, and they asked me similar question was, we don't know what a good day looks like. Or you're acting worse if someone tells you what this is supposed to look like. And then you go about and you're working hard, and you're not like your output because you didn't book a meeting or you do whatever, like, it's hard enough to go through it. But then if you're looking back on it, and you're sulking around, like, Well, I wasn't good, then it's just gonna make the next day. So you're just grim. I remember being in that seat looking at it like my first couple days as an SDR thinking like, I gotta do this every day. Like, I gotta do this. Again. I just made you know, 80 100 dials. I got to do it again. So perspective of what's good. I like to use this funny example. But it really to me it. It depicts what I'm trying to get across. But like, if an alien came down and decided to play baseball, right, in this alien had no didn't speak to anybody about what the rules were just got up there, as in the major leagues, and it was striking out seven or seven out of 10 times was failing, wasn't getting to hit the soundly and go back up to space and be like, quit, right? You throw I'm failing 70% of the time. This is the worst game I've ever played. Yeah, and you go back until his alien friends like I'm terrible at it. Right? But reality is a Hall of Famer. That alien, you know. So when it comes to being an SDR and if you're just getting started? Yeah, we talked about detaching from the outcome. But literally understanding what are the Connect rates? What are the conversion rates? Like? How many leads does it take to get into a conversation to have a chance, right? Because this is a game of numbers, and we are playing it in a long way. Right? So you need those averages to kind of to build up to see where you're going.
Jonathan Fischer 7:39
Yeah, that makes sense. So maybe to start setting the bar in a way that makes sense for people to feel like, hey, I can put my put my stamp on that day, that was a good job I did what I supposed to do every day feels like maybe that's ill defined for a lot of teams out there. What about this issue where you had all these social interactions that were baked into the job, you could go into the office, and you have that feeling of connectedness to the team? And all the things the things were just speaking about earlier? What are some alternative ways to fill that gap? Because those are really important things? Right? We need to be able to pick up on the best practices from our cohorts, and are our superiors. What what do you think can work now in this virtual space to fill that gap?
Jesse Gittler 8:27
million dollar question. And it's something that I think all teams and orgs are working towards. And when I look at it now as my job of running the entire organization, I have three managers and I'm not a manager anymore. So I'm no longer in the trenches as I once was coaching and doing those things. But when I think about it, people want to be connected. You know, and that's what they get when they come into an office and they see other people failing and winning, and we're part of the same thing and laugh at often take a walk. And, you know, that's possible to do remote, it's just harder. And when things are harder, they need more intention, right. So you need to actually plan and schedule and do them. You could call someone and say, you know, talk about went bad, right? It has a similar effect. You can set up group zoom meetings to, you know, I do icebreakers where my team, we just bring up a question and we talk just discuss, like, if you're sitting around in the kitchen, laugh off a bad call. Anything that promotes for me, when my managers they know that the best thing they could possibly do with their team. If they're where their time is spent, it's coaching, and it's connecting one or the two. And if you could combine both, then that's the best possible outcome for you and your job, you're going to get the most out of your people, if you're consistently coaching or connecting so you're not gonna be able to do that by getting everyone around in a room you're gonna have to be a little bit more intentional and set those times up and things like that, but it is possible.
Jonathan Fischer 9:51
Yeah, so a lot more one on one zooms, or even just picking up the old fashioned telephone calling. or what have you stay in staying in the space of people using too Technology. So we have as a theme today kind of advancing as a career. And I think we can look at that from both sides as well. Right? If you are a manager, probably helping to career path your people could be one effective way. You mentioned developing people as a key indicator for your own success as a leader in sales development. Maybe we can start though, by talking about the person in the chair, you know, how can he or she make some steps to make their career move in a good positive forward direction? And of course, you have your own background to draw on. So share with us if if your list if our listener is an SDR? What are some things he or she can begin to do today?
Jesse Gittler 10:39
Yeah, it's a very good question. And it's a very deep topic, I think. And, you know, I have these conversations with people all the time, obviously, of course, have a whole entire organization of SDRs, who want to get promoted, who by promoted hundreds, and put so many people in good spots over the course of the years. But there's also outside of my job, that I mentor, a coach that are just, you know, they want to talk about how to get promoted, and what they need to do. And I think the first thing, and I could only draw on my experience through my wisdom and what I went through, and everybody's different, but there's going to be specifically in the SDR world where you have people who are starting a career for the first time, or really just getting engaged with like a real work life balance and things of that nature. And there's, there's this kind of rushing feeling, right, where you see with performers early on that, you know, they get good, really fast. And then all of a sudden, there's talks about promotion, and they're like, where's mine? Where's mine, and I, I was literally like that. So I know that because I was that person. And I was lucky enough to actually get promoted when I was told I was gonna get voted. And my story was unique. I didn't know I wanted to get into leadership, I was like, I'm going to be a closer in this company. And when I got to that point, there wasn't a specific territory. And my manager, I had great people around me, so you should get into leadership. And that was that. But there were people next to me, right that were there longer than me. And that didn't get the role. And that left. And then I saw two years later, they sat you know, they're joining another company as an SDR like, and I think this feeling of having to get into that next role. I think, overall, everybody just needs to take a deep breath. Like, it's good. Obviously, you want to climb and you want to grow, and you want to make more money, and you want to get promoted, but people forget what a promotion is, right? It's more continuity, it's doing a new job for new people, you have a new boss, you know, so all of a sudden, if you're a really good SDR, and then I'll come back and talk about, you know, some stuff that you should do in order to get promoted. But I wanted to make the first point of that, you know, you should want to get it, but don't let it make, you know, a short term emotional decision right off of it, if you don't get a certain role, or a certain type of seeing too many people make that move. And there's something to be said, from someone who's went through all though, that way of thinking, like, you know, I used to be obsessed with money and be obsessed with promotion. And, you know, I switched over to like, you know, I want more peace, and I want more, you know, quiet in a way. And, you know, there's something to be said about being good at your job. Like if you're an SDR and you're good at your job, and you're making good money and you work well with your manager. Yeah. But as you get into your next role, the first thing is obviously, knowing what you want to do. You know, that's where it starts. And it's okay if you don't as an SDR in the beginning, because that's the point. It's really like keeping your eyes and ears open and doing your best job at the role and and seeing where it takes you. But talking to your manager about what that next role is for you. And if it's an ad, or if it's, you know, into marketing or whatever it is, what's the path to get there? You know, and I think this is where people are getting a little bit lost, and specifically into the magnet management career to like, you know, is there a window open? Probably not, you know, or is there a manager role open? Probably not, there's never, you know, you have to put yourself in position for when it does come up. You know, it's a very, very tough time right now. And there's, you know, you see what's happening in a lot of these companies with the layoffs and things like that. And all you could do, just like when you're selling is put yourself in position for when the prospect or your company has that position open, and they can move you in there. And if you can't get a time you at least get a path to there and being proactive. You know, more proactive what you're seeing what you're doing every day. I mean, it's the simplest things that will set you apart if you message your boss or manager as an SDR every day what your plan is going to be for the day and then how you did you will want to you will be in that have 5% of your of your group because nobody is going to stick to that. And that shows that you're organized, that you're detail that you care that you're taking ownership. And those things are crucial when you get into an AU role, because in a role is an SDR role with more responsibility. And that's what we want to see.
Jonathan Fischer 15:16
Yeah, yeah. Well, so the first thing you mentioned is probably really important to maybe drive home and that is, it may only be for you to get a promotion, like you are, if you're working a job, if you get really good at it. I'm, I may be reading this in jest you can correct me but I think I'm hearing you say is, hey, it kind of becomes fairly simple. If you can get good at it. And you got to get a really good relationship with your manager, you can show up and do your thing and get paid, that may be a better thing to stick with, if that's what you want. But that there's no there's no reason why we should rule that out. Right. That is one option. And then having done that little bit, okay, what would I really want? Okay, what's the next logical step? Is I miss what you're saying at all? Or do you agree disagree with that?
Jesse Gittler 16:03
I mean, I agree. I think it's worth talking about, right. I think it's worth talking about because people, they're obsessed with the idea of promotion, and I'm not, I'm not knocking it at all. Like, you know, I'm still I was there, I still am there still want to go and be, you know, whatever it is like, but it's worth talking about, especially nowadays, there are so many difficult even segments of the year, when it comes to holidays or summer, when it comes to selling that, you know, you go take an eight year old that's brand new, you find yourself on a planning 90 day, like there's so many different things that are possible from happening. And it doesn't mean don't want to get there and put yourself in position you should. But it's not about and I always tell this to my team, we promote here like crazy, we have a great process and a great path. But I always tell my team, it's not about being ready. It's about being ready to be successful. Right? Like it's not about like I am now Eclipse this SDR role and I'm ready to go be an A, it's are you ready to be a good a? Do you have those fundamental skills? So I think it's just worth thinking about talking about, you know, one of the biggest lesson I think, for me when I first left my original company years ago, that I didn't value enough that I try to help others when if they're thinking about, hey, I want to get this promotion, or hey, I didn't get promoted here. And I want to go jump to a different company here is the people, the people around you, right? Like, I went from a company that had 600 People were pre IPO when I was an SDR end up going public, it was great experience. And it was of course waiting for COVID It was in office and blah, blah, all that. But I love the people I was with, we had a great camaraderie, I had a brand that was built. This is another thing that people don't, don't think about. Yeah. And I walked into this new company, it was you know, eight people. And, you know, I didn't you know, everyone was older than me, I didn't have a lot of people to speak to. And I had to build myself entirely again. And like that paycheck that I got was nice, for like three months. And then it became baseline. And I was like, you know, like, right. Okay, next time I think about this, I think about who am I speaking to every day? How do they make me feel because so much of our lives are spent at work, you know, so it's just a big thing to think about.
Jonathan Fischer 18:26
Yeah, that's some really good stuff, Jesse things that that aren't maybe talked about openly enough. Like if you're if you're linked up with a company that really has their branding game on point, it makes your job so much easier, and maybe exponentially harder if when they don't, right, like if they don't know who that you are from Adam, it is an uphill battle. And now you got to be partially a marketer. Now, you can't just get appointments, if I'm calling from an established company, I can jump right in, is going to add several layers probably even to what my what what is even my go to market model looking like when my brand isn't well established, right? That's a big one and the people you're working with the team you're with, that's I love that. I know guys that have been really successful as managers who jumped back to str because they enjoy the simplicity of it, showing up rocking the phones doing their thing and being done. That said, there's a lot of fulfillment and growing, you mentioned about growing into the role by gaining the skills to be an effective AE and I assume to be similar. Once you're an AE, right, begin to think about what are the skills you can grow, to be ready to lead a team? Can you talk to us about that journey? What's that look like? If you're if you're looking from one position to that, let's assume you're in that that silo right? You do want to grow? What are some of the skill sets you should be working on as as an SDR to get to that next level?
Jesse Gittler 19:43
Yeah, I mean, you have to think about what the actual role is and then start doing some of the things that it's going to take a view, right and like if you're going to be a manager, if you want to be a manager, you know, and I somebody that I'm coaching on around this part, but he's an SDR and he wants to be a manager. And his current company doesn't have the manager thought. And it's very hard to get a manager job elsewhere without the experience that is truly very difficult. I mean, I wouldn't hire somebody when I was hiring for managers, I need them to have two years of experience with with reps. But it's proposing to your, your, your manager, if I was an SDR and there was no, I wanted to be a manager, I would I would go, I actually did this in order to get this director role with my boss. It's here's why I want this role. I did a PowerPoint, right. Here's why I want this role. Here's why I deserve this role. And here's what's gonna happen when really creating that. And was there a role open for me at the time? Absolutely not, when you're selling this people have budget all the time? Absolutely not. You have to put yourself in position for when that time does open up and being proactive with it. Like you have to step out of the lines a little bit, right, because this, it's most of the time, it's really just the start of promotion that's making you want it. But when you see someone who really takes these tangible steps to say, hey, here's what I want, here's why I'm on it. And here's what's going to happen. If I get this roll, then you'll see things start to happen. Pretty.
Jonathan Fischer 21:18
Yeah, I love that. So it really based more on leveraging the personal relationships, you have to gain the insight to know what do I need to work on is what I'm hearing from you. But you also put a pitch together, I like that. I mean, hey, you're in sales. So put the pitch together.
Jesse Gittler 21:36
Every single thing is selling. Like I tell this time managers all the time you're selling yourself to your reps every single day, what you do how you carry yourself how you talk, that's selling, that's going to either make them work a little bit harder, a little bit less, like, every single thing, it doesn't stop. So you're always constantly proving that out as well, right? If you want to be an AE, you know that okay, now I'm going to have to go and do discovery and run demos, what are some things that I can do right now that are not being asked me to put myself in position so that my manager looks at me and says that person? Is taking the first steps? Can you go? Can you go sit on demo? Can you go on a ride along with someone who's closing business? Can you run a demo on your own? Do you think that would you know, at least get some boxes checked for respect for the people who are running things? Like if it were me? Oh, yeah. You know, if someone came to me fearless and said, Hey, I'm gonna run this demo, check this out. Like, absolutely. So I think it's putting yourself in uncomfortable positions to grow faster.
Jonathan Fischer 22:37
Can you talk to us about what are the actual skills that you need to be able to work on just generically speaking, to be effective in leadership to operate in a role such as the one you function in every day?
Jesse Gittler 22:50
Yeah, you know, the biggest thing is what I learned when I first went into got into leadership was
actually leaving a territorial basis with a story, right, that helps prove out the point. But I was in the Rocky Mountains, territory, and I crushed it, right, I had a whole game plan of everything you needed to do every single thing, point by point. And as I was transitioning, I was handing over his territory to a new to new rep that just started. And I went to this rep and said, Hey, like, Here are the keys, right? Like, here's the paper, follow this exact thing, and you will win, like you will get it for one day, the next day, a little bit less, and the third day, and I'm in this cube with him, and I'm looking and I see him going off into his own things. And I'm thinking, why wouldn't this person just listen, I get just follow what I'm saying. And then you will win. And it occurred to me that like, that person isn't not me, right. And they have different ways of thinking different ways of doing things. And they're gonna learn differently. And they have different types of behaviors and habits and it's up to a manager, potential, whoever that person is. So when you go from individual contributor to a manager to a leader, you're not going to be able to get results the same way. It's not if you're behind, you're going to just shut everybody out and go make more dials and send more emails, like you have to work through people now and you have to understand who they are and what they want in order to get them to to succeed. And a lot of times it's different from how you would
Jonathan Fischer 24:24
Yeah, so you're it sounds like you're saying even the sales cycle itself is influenced in terms of how each individual rep might operate on that, especially if it's something along the lines of an AE or another higher level closer type person. Are there some books and influencers or their sources of input in your own journey becoming effective as a leader you can share with our audience
Jesse Gittler 24:51
never split the difference is a great book. I would definitely get that.
Jonathan Fischer 24:55
You have a Chris Voss Yeah, that's a great one.
Jesse Gittler 24:58
That's a great one just overall sales. influence I mean like six books at a time, like a little bit whatever I'm in the mood for what was gonna happen right here actually don't believe everything that was a big book for me recently is where I'm at where it's like, especially it relates so much to sales in SDR role, it's a quick read, definitely pick it up, don't believe everything you think it's, you know, thinking is less thinking more action, essentially, that's like my motto if you know, I mean, especially as an SDR, like you're thinking about what to say? What they're going to say how you're going to respond, what your managers gonna think about you don't lose track of the goal. So less thinking or action.
Jonathan Fischer 25:43
Yeah, love that, of that. So let's say somebody is in the AE role, and they want to get to your level, you talked about how you made a pitch to get that what are some other ways that they can grow? So if they're, if they're gonna get to know, you mentioned how you had it all mapped out, you crushed the territory, you had a recipe. If I'm gonna push back just a little bit on that, I'm thinking, well, dang it. That's the recipe. I mean, if I get if I get a really good recipe from Gordon, frickin Ramsay, and I follow it, the best I can, I'm still gonna probably get a good result probably still won't be as good as if it were him. But I like legit made beef wellington at home for my wife, okay. And I rocked it, man, because I just followed, I followed the man's recipe. So where's the differential there helped me out with that, like, shouldn't they just be learning your recipe? I mean, after all, you put a lot of hard work into that.
Jesse Gittler 26:38
Once again, you're not wrong here. But the point is, as a leader, it's not. People are not going to do what's best for them. This is just a natural human flaw. And it's a very, it's a very tough piece, right? Because every once in a while, you get someone who listens to every single thing we say as leaders and they crush it. Right? But it's just not You're not that's 5% you're just not going to have that happen most of the time. So yes, your point, should he have just listened I, there's part of me that says yes. But I also learned a bigger lesson that like, Hey, I have to communicate differently to different people. And if you're someone who wants to get into management, or you're an AE that wants to get into management, or even SDR, you know, how can you level up the people around you? Right? If you know that the goal of the manager is to make your people better? Can you show that? And where most people get this wrong, Jonathan, are when I you know, when I speak to people who are trying to do that? It's yeah, I wrote a script, or I gave my talk track to a bunch of new hires, because it was working. That's great. How's it? How's it working? How's it worked? Like? Most people can't answer that question. Is it actually working? And that's a big part of being a manager, and essentially, even more so as a director now, is that, can I track? What results I'm trying to achieve? And can I prove it out? Because if you're an Strnad, and you have something that's working without tracking, and then present those numbers to your director, your VP? And they will be impressed with that, because that's ultimately what they need you to do as?
Jonathan Fischer 28:14
Yeah, for sure. Do you like to work with people who have some experiences SDRs are helpful, they at least they know, they know, it's a grind, they know a little bit at least a baseline of what to expect is that that shorten the curve a little bit do you find
Jesse Gittler 28:27
you know, I would have to say, I had to date one side or the other. I've had much more success just in general with people with completely green. You know, hiring in general is so many people think that you put it in a box and you got to do this or see this like really I look for people who are smart, who care we're gonna work hard, who are organized and of course those characteristics that agree and coachable and things like that, but giving shit like for the greatest things that I've seen, and it's easy to prove that out as a new rap because most are just
Jonathan Fischer 29:07
Yeah, I love it. Well, you can find 1000s of people who give a rip and want to do really well on the overclass overpass talent marketplace is the world's leading source for quickly hiring, pre vetted highly effective professional STRS AE sales managers in the life you can build a team in days instead of weeks, you'll be shocked at how economically and how quickly you can do so go to overpass.com create your free account and discover it for yourself. Well, Jessie, it's been a great conversation. How can our audience go further with you? Should they look you up on LinkedIn tell us how we can reach you.
Jesse Gittler 29:39
Yeah, LinkedIn is the best place. Jesse Gettler. You'll see me on there. The me if you have any questions, I will I will do my best to get back to you. Okay, awesome.
Jonathan Fischer 29:49
Well, thanks so much for being a fantastic guest on our show today, Jesse. Thanks so much. And thanks for audience for making it such a successful show. Hey, tell a friend and come back and listen for the next episode. We'll see you then
