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January 5, 2023 · 13 min read

Season 2, Ep. 32 – Meet the team: Sales Development Rep, Greyson Wooten

When Sales Development Representative, Greyson Wooten, wanted to make a career change, he did a full 180. Or did he? This week, Faith chats with him about moving from teaching to startups, being passionate about sports, and how if you can handle the wrath of an 8th grader, you’ll excel in sales.


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Faith (00:06):

All right. We’re in business. Welcome to the Frontier. Greyson, have you been on before?

Greyson (00:11):

I have not. I’ve been watching from afar on LinkedIn and YouTube.

Faith (00:15):

Oh, nice. I, well, I’m not a YouTuber. This is very new for me, but we’ve got one YouTube video that has just gotten a ton of traction, that it’s just like, a staff interview with Regis. So I think I need to join to like, see what the, what all the fuss is about <laugh>.

Greyson (00:36):

Yeah, absolutely. No, and yeah, I’ll need to go see that. ‘Cause I think I saw that video posted on the LinkedIn, but I didn’t click the actual YouTube link itself, so yeah. I wanna go see how many views it has.

Faith (00:47):

<Laugh> I know. It kind of surprised all of us. We were like, we’re, this is not, not what we’re expecting. Well, Greyson, I’m really excited. This is your staff interview, so it’s a chance for everyone to kind of get to know who’s working behind the scenes here to make things happen. So, we can kick things off with just a quick introduction. Who is Greyson and, you know, where do you live? How did you find yourself here?

Greyson (01:12):

My story on how I got to Gun is pretty, it’s not straight, but (Faith: <laugh>) everything kind of, when I looked back just everything seemed to have kind of aligned for me in an interesting way. But I’m currently living in Texas. I was born and raised in Texas, and immediately after graduating college, I found myself back at home teaching and coaching. I’m a huge sports fan fanatic. Any which way you can say it. I love sports. And so that was kind of how I felt, found myself in education. It was just a passion for helping people just better themselves and kind of overcome obstacles mentally, physically. That was, that was how I ended up in education. And I was an educator for six years both at the middle and high school level.

Greyson (02:05):

And after my sixth year teaching and coaching I really just had a lot of thoughts about wanting to know what else was out there professionally that I could possibly be good at. I wanted to just see what the world was like from outside of a classroom, and that kind of is where my job hunt started. And it takes time. (Faith: Mm-Hmm. <Affirmative>), I know some people are fortunate enough to be unemployed and get work relatively quickly just because they’re qualified and they find that right job. But for me it was a process of interviewing and being told no, and being kind of told, Hey, I’m not the right fit, or I don’t have quite the experience that they’re looking for. And so after two and a half months, I finally was able to get my initial interviews with Gun.

Greyson (02:55):

And I think that was kind of the point for me where I really became intrigued with Gun, just because the people that I got to meet. So, I think the first person I interviewed with was Ben, who is pretty much integral in my day-to-day life now, as a member of the sales team. I interviewed with Ben; (Faith: Mm-Hmm. <Affirmative>), I remember that interview well. He just brought a ton of energy, made me feel like I was already a part of the team. I believe my second interview I interviewed with Teja, the CEO. (Faith: Mm-Hmm. <affirmative>). That was very eye-opening for me, because just not having ever worked in an office space or in a corporate environment, I never saw myself having a conversation with somebody that had the title of “CEO.” So I can vividly remember having the interview with Teja and it being so just relaxed. It was just interesting to me to be talking to the person who created Gun, had a hand in everything it’s become, and a person of that status kind of taking the time to talk to me and interview me (Faith: <laugh>). But after the interview process, I did well enough and impressed the right people that I was offered a position here as an SDR. And that’s what I’ve been doing for the last two and a half months at this point, now.

Faith (04:17):

Crushing it. I also cannot let Teja listen to this because I feel like you calling him a person of status will really go to his head. So we’re gonna put this on the no-listen list for him <laugh>.

Greyson (04:30):

And I was gonna say, I clearly know Teja. I’m a new friend of Teja’s. I’m recent to the company. So yeah, if that’s something that needs to be edited out, feel free to, (Faith: <laugh>) feel free to ax that, but-

Faith (04:45):

Oh, no, it’s all good <laugh>.

Greyson (04:46):

No, he just, yeah, it was, it was just a great process. 

Faith (04:50):

I love hearing from folks who also move from teaching to working at startups, because obviously that was my path, too. That was yours. We’ve had several folks on the team who are former teachers who, you know, moved into the startup world because the energy is really similar, right? And the challenge at hand is really similar. So I’m curious, like how many times a day do you feel like you’re drawing from your experience teaching?

Greyson (05:16):

One of the biggest things that I learned as a teacher was perseverance. And that word gets thrown around a lot, and it gets used a lot in a lot of different ways, but my experience as a teacher was, you really, I mean, you have to learn how to persevere because it is, it’s a really tough job. And I think that when you can get mentally strong enough and kind of learn how to spin negative situations or obstacles into things that become challenges or things you look at positively as a way to improve yourself, I really feel like that’s what education taught me. And so going into sales, that was something I heard repeatedly, was you have to have grit. That was, I think, the phrase I heard most often. And that is a characteristic that I don’t, I’m not trying to brag on myself, but I can honestly say that I think I developed a lot of grit in the classroom as a coach, as a teacher, and an ability to kind of take each day for what it’s worth.

Greyson (06:16):

Don’t let one bad day make a bad week. I know in education, you’re (Faith: mm-hmm. <Affirmative>) in charge of hundreds, sometimes tens to hundreds of kids, and they can drive you up a wall, but if you don’t learn how to kind of reset each day and make each day it’s own kind of new adventure, you’ll just get stuck in a negative head space that won’t be good for anybody. And so I think that’s been the biggest transferable skill, is the ability to kind of leave today as today, whether it was good, bad or otherwise, and move on to tomorrow and just see what tomorrow holds. Because it’s just a brand new opportunity and you never know what could happen.

Faith (06:54):

I feel like, specifically in sales, the constant rejection from children probably helped prime you a little bit. At least I felt that way when I joined the team here. My job was to pick up the phone and call everybody who signed up and, you know, be like, “Hey, I know you didn’t want a phone call, but I’m calling you anyway.” Some people were really excited and they’re like, “Man, this is cool. This is obviously very different than any other hiring solution out there.” But also there were plenty of people who are not excited to hear from me. And, you know, nobody prepares you for rejection better than eighth graders who just think that you’re the most terrible, embarrassing person in the world. So, and what…do you feel that way too?

Greyson (07:42):

Yeah, no, I think that that’s a great way to put it. In all my preparation for this job, I went through a course with a company called Vendition. And just through my general interview process, people always ask me, “Do you have experience cold calling?” And I’ve never had a sales position. I’ve never, prior to this, I’d never done anything in sales. But I will say there’s nothing probably that I can think of closer to a cold call, within education, as having to call students’ parents unannounced, because it’s essentially the same thing. You’re calling somebody who (Faith: Oh, yeah.) usually is not anticipating hearing from you. And most of the time, unless it’s for a good reason, I would say a lot of parents don’t like getting calls to hear reports on their children misbehaving. So, that was a skill (Faith: <laugh>) that I didn’t know that I was developing. (Faith: Yeah.) But cold calling to me is, it’s still something I’m very much learning how to do and master. But the interactions with the children and very much so interactions with parents, I think prepped me for that, in a way. But to your point, it is, (Faith: Mm-Hmm. <Affirmative>) when you can, when you can sit there and have a child kind of tell you, I’m not gonna do this, or I don’t feel like doing this. I just think that there’s, it’s an easier transition when you’re speaking to an adult who usually will put it a little bit more eloquently, and yeah. Not be so (Faith: <laugh>) abrasive about it.

Faith (09:07):

Yeah. In my case, it wasn’t kids saying that they wouldn’t do something. It was more like kids telling me they didn’t like my haircut or my shoes <laugh>. So at least adults aren’t that mean, you know.

Greyson (09:19):

I was, yeah, I was…that sounds…I was thankful I never had personal attacks, but I did have a fair amount of students who just would tell me, I’m not, I’m not gonna do anything in this class. And I mean, to be fair, there was no way I was gonna force them to, so it just became something where I had to learn to be patient, right? And yeah, not let my emotions get the better of me and just make my way as best I could through that day, through that class, that moment. (Faith: Yeah.) So, yeah, never look back. You just gotta keep pushing forward, I guess.

Faith (09:50):

Okay. So, you know, your role here at Gun, obviously, I think listeners can catch on, you’re doing outbound sales, you’re calling folks, and so primarily the job here is getting more developers hired. So I wanted to clarify, I didn’t know if we touched on that yet. So yeah, Greyson, since you’re outbound sales and what’s cool is like, you and Donovan are our first outbound sales folks, and so you not only are new to sales and new to working in tech, but you also are creating a new department. So I’m wondering like, what have been the most important lessons learned there as you kind of figure out this new function within the company?

Greyson (10:35):

For me, it’s really just been something that in education, I was the opposite end. I’ve had to really just become a sponge taking in as much information as I can. And again, I was teaching for six years, so I was really used to giving the information. And in education, you’re constantly learning new things, but it’s just very different. I’m taking as many notes as I took in college. I’m writing things down more than I’ve written them down in a long time. Even as an, even as an educator I don’t feel like it was just different. It wasn’t, it wasn’t notes, because it was new information. It was usually reviewing things. So, this experience has been so amazing. And yeah, to your point, it feels even that much more special because I know I’m in…I’m one of the first people, I’m one of two in a position that hasn’t existed before in Gun. And to be somebody without a sales background, to be somebody without that experience that a lot of people told me was so valuable, and to be given a chance to, to hone my skills and become a better salesperson, so to speak, it all just feels really, really great. 

Faith (11:50):

Cool. That’s awesome. <laugh>

Greyson (11:52):

I just, yeah, no, I think that, yeah, every day is something new. Honestly, I learn something all the time from different people every day.

Faith (12:03):

So, outside of work, when you’re not here at Gun, what are you passionate about? What do you like doing?

Greyson (12:10):

If the timing is right, I honestly just love spending time with friends and family when, when that works out. I mean, it doesn’t really have to be anything in particular. I honestly like sitting outside on a nice day, just talking to, to friends and family as much as anything. Very big cinema fan. Love going to the movies, love watching movies. It has been an interesting contrast with this being my first remote job, finding that balance between working inside and getting everything done that needs to be done, and also finding that time to get out and exercise and yeah, just be outside in general, honestly. (Faith: Yeah.) Just, I would say…passionate about the people I care about, passionate about, I love movies. I don’t know if they’re a passion, but they’re definitely a love, and then sports. Right now, the World Cup is, (Faith: That’s a passion.) is going on. (Faith: Yeah.) So, okay. And I, well, and I appreciate that. I would say some people have told me “That’s just a hobby.” It’s…maybe if I was filming or, or more involved in some way, it could be a passion. But without sports…watching, participating I, yeah. I don’t know where I’d be.

Faith (13:20):

Have you watched Welcome to Wrexham? I feel like it’s the first thing that’s made me understand what people see in sports, like, why people love it so much.

Greyson (13:32):

And I’m honestly, I’m ashamed that I haven’t, but I know exactly what you’re talking about. And I even have Hulu, so there’s really not any excuses. I think that I’ve just been putting it off or watching things I’ve already watched a million times. But I actually, yeah, I love the guys that did that: Rob McElhenney and…

Faith (13:55):

That’s so (Greyson: Deadpool.) funny, because usually they say…yeah, Deadpool <laugh>. Yeah, usually people are like, oh, it’s Ryan Reynolds and the other guy. So it’s funny that you know Rob and not Ryan <laugh>.

Greyson (14:08):

Then to, just, to be honest, I’m an It’s Always Sunny fan, so that’s really why he comes to mind really easily. But I mean, Ryan Reynolds, he would’ve come. I just, I think it’s the, it’s the passion of cinema kind of takes up a larger than–

Faith (14:23):

It’s Always Sunny.

Greyson (14:25):

Yeah. It’s just, I have too much movie knowledge, too many names that I don’t need to know. So sometimes, yeah, finding the right one is difficult.

Faith (14:34):

<laugh>. All right. Well, that’s your homework, after we hang up today, is put on an episode of Welcome to Wrexham.

Greyson (14:42):

Consider it done.

Faith (14:43):

Awesome. Easiest homework you’ve ever done, I assume.

Greyson (14:47):

Oh, without a doubt.

Faith (14:49):

Thanks for listening to The Frontier Podcast, powered by We drop two episodes per week, so if you like this episode, be sure to subscribe on your platform of choice and come hang out with us again next week and bring all your internet friends. If you have questions or recommendations, just shoot us a Twitter DM @thefrontierpod, and we’ll see you next week.