The Sales Engagement Podcast
The Sales Engagement Podcast

Episode · 10 months ago

Land Your Dream Job in Tech Sales

ABOUT THIS EPISODE

Most of us in sales didn’t wake up one day with a calling (although the ones who did are a force of nature, too).

We discovered it accidentally... or because it was the first job we could get... or by word of mouth... or because we read something about how great it was.

Recently on Sales Engagement, we featured the stories of three onetime SDRs who talk about how they discovered their dream job:

What we talked about:

  • What life was like before they found tech sales
  • Their path to SDR and beyond
  • Career advice and encouragement for new SDRs

P.S. Outreach is hiring SDRs!

For more engaging sales conversations, subscribe to The Sales Engagement Podcast on Apple Podcasts, on Spotify, or on our website.

Listening on a desktop & can’t see the links? Just search for The Sales Engagement Podcast in your favorite podcast player.
 

Welcome to the sales engagement a podcast. This podcast is brought you by outreach, the leading sales engagement platform, andthey just launched outreach on outreach, the place to learn how outreach.Well does outreach? Learn how the team follows up with every lead in recordtime after virtual events and turns them into revenue. You can also see howoutreach ones account based plays, manages reps and so much more using their ownsales engagement platform. Everything is backed by data pulled from outreach processes and customerbase. When you're done, you'll be able to do it as good asthey do. Had to outreach don io on outreach to see what they havegoing on. Now let's get into today's episode. All right. Next upwe have Steven Farnsworth, who has gone to more of a marketing route.We're going to go into some more depthod kind of his path. It's prettyunique and pretty cool. But yeah, thank you so much, Stephen,for jumping on. Awesome, happy to be here. Thanks. Thanks forinviting me, Sam. Okay, all right, so we are going totake this back to before you are an star and actually, just so everyonenoticed, and Steven were roommates in college and so we go way back.But just for the audience, talk about a little bit about your career beforeyou became an s year now. Thank you for calling that out. Ithink it's important for people that know our you know, long standing relationship.I'm sure you'll ask about this later, but obviously I was at outreach inNstr in the first place because of you. Yeah, it's been a long timecoming. So before I was an str just riot at a school.I actually went to a kind of sleepy insurance company and was part of theirkind of founding strategy team, and so I reported to the President and essentiallymy team was the executives, lackeys who just owned projects that really didn't haveowners but were high priority, and my team's job was to just figure outwhat do we do here? How do we operationalize some of the some ofthe potential like problems that existed? How do we operation one some of thesolutions? So that's that's what I focused on before moving into anything tech focused. Got It. Okay, so that's what you're working on. Corporate Strategyand Insurance Company, and I mean it was a decently good job, likeyeah, it was. It was a sleeping church company, certainly compared tolike, I don't know, one of the fastest growing SAS companies snared America's, but it was, I mean that wasn't an easy decision for you toleave that job. I think it's important to call that out. Like howdid you make that decision? Had you justify that to yourself? Had youjustify that to your wife? Want to do that? Yeah, so,first of all, you're a good salesman, so you were. You were callingme pretty frequently saying hey, you got to come join, join getinto tech for me. You're right, I I guess I didn't view itis a sleepy insurance company. Back then it was a it was a reallygreat job. Again, I had a lot of executive visibility, worked onhigh priority projects. My last project, I mean I was I was kindof the lead on an acquisition of one of our primary competitors at this company, and so it was certainly like a really fun interesting role and, likeyou said, it was a mean I made great money for me. Itjust it felt like a really good place to be in. What I struggledwith, and I think it's something probably a lot of people struggle with beforethey get into strs. We certainly saw this with new SDRs at outreach fromfrom where they came from. Is that in some some cruisers just not alot of mobility, and that's kind of what I looked at it. Thissmall little insurance company is I started to struggle with. Okay, if I'mhere five years, ten years, twenty years, I saw that, likethe industry in the knowledge that I had was really only applicable within that verysmall kind of type of insurance. And so for me, I frankly wasn'tthat interested in being in SDR. But what I knew were the facts thatif I wanted to get into tech,...

...generally you get in to tech bybeing technical or nontechnical. I wasn't very technical. So if I'm non technical, the route that is seemingly the most natural to go into and it's themost available. At least he's SDR, and so I kind of fell intoit. And obviously, on the side, you'd been an SDR for a monthor two longer before I joined and had been calling me saying hey,this is this company he's blowing up. Come join and learn what it's like, love it, and okay, so I'm going to embarrasst even a littlebit more. Here he was, Stephen, you went to a great college.You, I think, maybe got one grade less than than a andall of college, and this guy didn't even study. So he's like favoritesmart and he's working at this school, kind of impressive job, making alot of money, and then all of a sudden you become an str andnone of that matters. Like what we've had experience like, and what gotyou through that part, because that's a I mean that's the risk that somepeople are scared to take, and I'm sure a lot of people are listeningthat are in a similar situation. What was that like for you? Yeah, so I want downplay how much of a hit it was to my egolike that was, frankly, maybe the biggest piece of my thing that Istruggled with when I left this other company is, again, I was involvedin a lot of the decisions at this other company. I had a lotof visibility, like I mentioned earlier, when I went and joined outreaches anSDR. You know, as an str you generally don't have much influence onthe business, if any at all. Your job is to is to producemeetings for account executives and for me that was hard for me to be partof and just to look at peers and others in the company, whether itwas in product or marketing or, you know wherever, to know that Iwas just viewed as Oh, here's this, you know, kind of entry levelSDR and to have so little influence. It was really hard for me.But I think that the positive of being an SDR is is you cancreate your own kind of create your own luck and your create your own sixsuccess. So for me, Sam had been helping me get the job,had pitched me and said, Hey, I think Stephen will be really good, and so for me it was being able to both meet those expectations andthen exceed those expectations, which I had full control over, and so that, I think, str you have that control, and that was big forme, is to I could out work anybody and I knew that and Ifelt like some of the business, business experience I'd had before would be especiallyrelevant when trying to call business leaders and set meetings with those business leaders andto have intelligent conversations with them to even get them to agree to a meeting. And so I did feel like I had some you know, I thinkkind of extra benefit there in joining us an str that's awesome. And Yeah, when you talked about that, it reminds me that that was actually kindof a big deal for me to I haven't really thought about that for awhile, but before I became an Stra is was cee of my own twopersons start up. It wasn't that big deal, but, like I thoughtI was cool and all of a sudden now and linked then I've Ben strand. Yeah, it was. It was definitely like a little bit ofan ego trip for me, you know, in some ways, probably healthy forme. Definitely. Your point, though, you had, and thisis probably something for other strs to think about, is, you know,if you're coming right out of college or high school or whatever it is thatled you to be an str and, you really we don't have any sortof relevant business experience yet, especially as it connects potentially to the buyer thatyou're supposed to be pitching. Like I'd encourage anybody to try to like putyour put yourself in those shoes of who you're selling to for for a periodof time, because it's the end of the day, like you can calland have you follow a script pretty well and that can get you, youknow, a long ways, but being able to step outside of that andhave an intelligent conversation with someone is is really important and I think it wasa big part of my success that outreach as an str based on kind ofthat previous experience in my ability to talk...

...to sales leaders. Yeah, it'sreally important and I think that's important too, because a lot of times we thinkabout str with you go people who come straight out of college, thisis their first job, and maybe if you're not in that situation, youkind of missed the boat. But that's not true at all. Like alot of the most successful stars ever have been people who have come from totallydifferent industries and learned it from scratch. So, yeah, pretty cool.I agree. There's I mean, I think back on a lot of thesuccessful people outreach in the stir worlds came from like recruiting, so maybe theyhad some level of experience selling before others came, you know, or teachersor writers or I mean, it didn't matter. But I think the pointis is they use the strength and the experience they had to help set themselvesapart. Love it all right, so let's move let's move on to thedirection you took after your time as SCR. You went to the marketing path,which not a ton of best air is going to but I think it'sawesome direction and I want you to tell me a little bit about tell mea little bit about that, why you decided to take the marketing ro ountand how it's worked out for you. Yeah, so here's what I'll say. Is I was an SDR. I enjoyed my time as an str anda lot of that, again, came from being able to create Mindsey myown success. But I did miss some of the role that I'd had before, like being more involved in the kind of strategy of the business and workingmore with the executive team to have influence on the business. So for me, I ended up for a period, I you can't forget this, andwe were SDR managers together, and so I managed some of the str teamwith you and for me I just felt that, you know, sales inbeing involved in any sort of sales motion directly was not for me. SoI wanted to get closer to more of the the product and and so itoutreach. I ended up actually getting involved in leading kind of outreaches, integration, ecosystem and really any partner that wanted to work with us. But thething that I found most exciting is wasn't necessarily the relationship management of working withthose partners, but was more in figuring out, okay, now that wehave some relationship with this person or some integration that's been built, how dowe actually take that to market, like how do we make it something that'sbeneficial to literally to like revent, to create and generate revenue for us inanother partner? And so I got really involved on the go to market side, which kind of naturally put me in a product marketing role over time,and that's that's where my career has really I've got a double down since then. I love it and I want you to correct me if I'm wrong onthis, but I've always thought of marketing is being kind of a cool pathfor an str if they want to take it, because the experience of anstr is really and the outbound in the outbound scenario you are calling people whohave no idea what that reaches and getting them from knowing nothing to want totake a meeting to learn more, and it seems like an experience in anintuition that would serve you well in a marketing capacity. Would you totally likethat was true for you, Oh tell, I think first of all, justwhat you mentioned of how do you just describe something in a very quick, fast way to be able to educate somebody on the pain that you solve? I think is important, just understanding how that works. And Yeah,I think that marketing gets a bad rap sometimes for just like being so disconnectedfrom sales and saying things that like they then hand the sales and says,I would never say this or there's going to connect with this. So Ido think that having that sales mentality and that experience is like a differentiator inmarketing. Like, I was the only at outreach and we had, youknow, over the course of my time in reporting into marketing for maybe threeyears. I can't remember if there were more than honestly, I think Iwas the only one that came from the sales route and I think that wasreally useful and being able to help connect to sales be because at the endof the day, obviously marketing job is to be able to create and makesales job easy and if people can't connect...

...to the sales. You know tothe sales people and you know, how can you be successful? Yeah,love it. Okay, so I guess. Okay. So for the last question, I want to talk about if you could go back in time andgive yourself advice from starting as an str what would that be? It's agood question for me. It's something that you did much better than I did, first of all, at which I was always jealous of, is there'san element of being shameless when you're in sales, of being able to takerejection in stride with trying new and kind of experimental things. I think forme, I've generally lived a lot of my life like following the rules prettyexactly, and I kind of the rules of engagement or whatever, and Ithink that something that you did and some of the other really successful astrs didat outreach were just kind of finding new and unique ways to connect with peopleand being willing to let that blow up in your face if it didn't work. And I'm scare you have lots of stories that you can share there,but like, I wasn't. I wasn't as willing to do those things andI think that I I wish I had. Love it good advice. Really,this has been really a great conversation. Really appreciate it, Stephen. Andyes, Steven went from corporate strategy St are in a marketing it's beenvery successful in marketing. Thank you so much, Steven. It really appreciateit. Cool. Thanks, Sam, pretty you having me on all right. Now we have Roberto Carrero here. Roberto is an a here that reach. He's come up through the ranks and we're going to talk a little bitabout his path and where he has taken it. So thank you so muchfor being on, Roberto. Hey, Sam, thanks for having me righton. Okay, so let's start out with what you did before. See, are so get just give me an idea of what your path was,what you did before and kind of how you heard about yeah, so Iwas actually an account executive at two different companies. The first was called theFlyer Media Group, so actually sold direct mail services business to business, andthen the second position I was in account executive at NBC Universal, so Iactually sold television commercials, also business to business. So bit of an unorthodoxpath into SDR land, for sure. Love it. See you did ae work before str and. Had you had you heard about us? Therebefore. You Got Nut Chair job. I did not. I did not. I remember going home one day and just typing into Google, you know, what's the highest paying sales job that I could get, and I sawsoftware sales was the number one highest paying roll. And then, you know, I saw the str roll from there and from then I just divided theplan to get in. Well it. Yeah, I think I don't thinkthat's that uncommon of an experience. I think a lot of us that arein tech cells right now did that research and realize, say, like,there's definitely somebody to be made in tech sales and obviously, like we thinkabout your position do you have right now? Ae is kind of where the bigmoney is, and there's actually a surprising about of money in the SDRrole, which a lot of people think is kind of the precursor. Butand it's like a hard job and stuff, it actually pays decently well. Like, what was that like moving from a e to str financially for yeah, so, believe it or not, I made as much money in sixmonths as an str that I did in the entire year in a non techrole as an ee. So bit of a difference. Yeah, that ispretty awesome. And so, yeah, you wanted the role you wanted,you know that could the upside was higher in tech. It's also for me. It's also just seemed like a fun place to be, you know,a hundred percent, hundred percent. I mean if we're looking at a companylike outreach, obviously there there's so much...

...culture. We had, you know, a lot of people that were my age within the company, you know. And Yeah, it just seemed like a really good spot to get into. So highly recommend it for anybody. Yeah, totally. And also theother thing I'd love about tech is just how crazy it is to have acompany that grows as fast us as a tech company is expected to grow.It is not warring, a hundred percent. There's always going to be something youaround the corner. There's a lot of opportunities for growth, which is, you know, what I was looking for in a new job and,you know, it hasn't disappointed by any means. Yeah, awesome. Andso so tell me more about what the experience was like for you, kindof being an str most like. Yeah, so I always like to frame itin this context. To be honest, it was a little tough, right, and this is why so, you know, coming from a traditionalmedia role that was, you know, be to be and outside sales,you know that there was only so many people that I could reach in oneday. Right, so the amount of times that I would then get rejectedor get told no was significantly less. Right. But you know, comingto you know, a high growing tech company, you're using sales engagement platforms, you're, you know, heavily on Linkedin, you're heavily prospecting. SoI would say your rate of rejection is increased exponentially as an str and that'snot something that you can get used to until you actually do it. SoI think you know, the first quarter to we're tough just mentally, butonce you get over that barrier, your pay is going to increase, you'regoing to grow a lot professionally and personally, and then it's really all up fromthere. I love that. I think that's a really, really goodpoint. That a lot of that's done to it for a lot of newSTRs is that the absolute number of rejections that you get as an sty areis really, really high. Yeah, yeah, like that, but youhave to you just kind of have to get used to thinking about things inrelative terms, like the more you do in any area of your life,the more bad stuff happens. But morgod stuff happens too, and so yeah, I think that's really important. Like understanding that the absolute number of rejectionsis not a reflection of failure is a big deal for a lot of people, and so I'm glad you brought that up. I think that's that's superimportant. Yeah, absolutely. Okay. So next thing is I want youto tell me about the direction you took after your time as S. Yeah, this is what there are a lot of strs out there who want togo to the path of an AE, and how has that path been foryou? Yeah, so one thing that I'll say to anyone that wants tobe in a e you know there might not always be a path that's laidout for you right away. There might be, but chances are there theremight not be right. So what I'll say is, if you're in thatsituation, you've got to create the path yourself, and that's something that Idid when I was an str. So I'll give you a couple of examples. Right, if you're an str that wants to be in AE, yougot to start thinking like an ae right now. Right. What does thatmean? You know, start teaing up good meeting, you know, takegood notes, perfect your craft, get a mentor. That's a AE.You know, start doing things at an a e would do right now,and that's really what I did and that's really what put me in a positionto eventually get promoted. Awesome, and as as an AE right now,how has it been for you? Happy. You took that path. A hundredpercent. A hundred percent, and I actually think that, you know, being an str set me up really well for being an AE. Youknow, there is a specifically at outreach Ay, we talked to a lotof people that are in the sales development, so it's really good to connect thepeople on that level specifically. But also that the skills that you takeas an str, you're not going to lose those as an AE. Right, you still need to prospect as an...

...ee. That's not going to goaway just by getting promoted. So that's something that I still take with metoday. And then you also you are going to have to interact with yourstrs, right, you're going to still have to partner with them, soyou're really going to be able to relate with them on that level by doingthe job. Awesome. I love it. And yeah, former SDRs have avery or former outreach hastyard have a very good brand as a over thatreach that we've had a pretty remarkable success rate, and so there's definitely sometruth of that. You get really get a prospecting, especially through a salese gage from platform. It gives you a huge advantage and it's probably whyyou've been able to be so successful. So that's great. Okay, lastthing is any advice that you would give yourself when you're starting out as anest are there? You go back in time, what would it be?Yeah, honestly, I think it's those the last couple things that we mentionedright. I think the number one thing is you've got to develop a strongmindset, right, like we talked about. You know you're going to face alot of rejection in the role. You've gotta you've got to be inthe right mindset to handle those things. You know you're going to face alot of rejection, but you're also going to get a lot of wins aswell. So you know, learn from the mistakes, focus on the winds, move forward from there and then you know, figure out what you wantto do in the future. You know, if it's the AE roll and you'vegot a you've got a forge a path to get to that right geta mentor start thinking like an ae right now. You know, listen topass demos that you set those meetings for. You know, start doing the AEthing right now, and then when that opportunity arises, you'll be ina really good position to get it, love it. And Yeah, Iwould echo that and I think that Roberto is also a very good example ofbeing an all end kind of guy. Like back in the day, backbefore we were remote, Roberto, in order to be in a had tomove all the way from Tampa to Seattle and he was willing to do it. He just kind of made it happen. So, Roberto, good decision.Thumbs up or thumbs down on that decision. Thumbs up all the way. I mean there's going to be, there might be a time in yourcareer where you're going to have to make that sacrifice. Right, some positionsare only available in certain places and you know, I don't regret it atall. You know that the move from Tampa to Seattle was a great one. Yeah, highly recommend taking that risk, especially at this point in your career, if that's a situation. Awesome. All right. Thanks so much,Roberto. Really appreciate it and Yep, have a gree weekend, you two. Thanks. Am All right. I'm here with Megan Donovan. Sheis the sequence specialist of that reach right now and we're going to talk throughkind of where she came from at what her experience was like his Sdr andkind of the direction she except. Thank you so much, Megan, forwilling to jump on and chat about this with us. Of course, Sam, thanks for having me here. Awesome. Okay, so just a level set. I want to talk a little bit about what your background was beforeI stare stairs. Come from a lot of different spots. What was yourbackground? How was your path into it? So before I joined the outreach familyas an str I was in retail sales. So I worked at largepublicly traded fortune five hundred companies like Nordstrom, Bank of America and hurts. Sothat's where my passion for sales kind of began and, of course,helping people. So I knew I was passionate about selling. It just didn'tline up with the company values of like a larger, larger brand. Loveit. So where did you initially hear about string? where? where?How'd you get introduced to it? So I didn't hear about string until Iactually put my application in for outreach. I knew I wanted to make thetransition out of retail sales. I saw...

...the sales development representative posting on indeedfor outreach and I Google the company started to look into the product and whatit had the ability to do and some of the company culture and I wasimmediately intrigued by that. Love it. And then why did you want therole? Did you? Why do you want it? Yeah, so,like I said, it came from bigger companies. So the biggest thing forme was working for a startup. The ability for career advancement and operating morein the sense of like a family than a large business lined up with myown goals and values. I previously had experience selling, but I was neveran assass be to be setting. So the SDR role gave me that basicknowledge to kind of articulate how we can help other businesses with different workflows andtext acts and kind of get my feet wet and the Sass world and didit live up to your expectations? It did. I think I'm as Sasserfor life. I'm never going back. Definitely found my passion, love itand I guess what we're some of the what were some of the things thatthat were different than you expected, and in good ways and maybe some waysthat were not quite as good. So previously in my past sales environments itwas kind of a everybody for themselves environment, so I was expecting this role,are the str role to be the same as my previous sales jobs kindof had been. That was definitely a surprise and I don't joined outreach.It was way more of a fun learning environment where everyone's in it together,everyone's got your back. So there's obviously going to be some sales along theway, but everybody kind of fails together wins together. So that was ahuge surprise. I didn't think it was it was going to be that way. Definitely challenging, but it helped me undoubtedly strengthen my communications business skills.So would recommend it no matter what career path you're taking. Cool and thenyour path out of str is kind of unique. Into your current role,you're a sequence specialist. It's kind of a new role, the one thatI expect will become more and more common in the future. So tell mea little bit about why I kind decided to take that direction and what yourexperience has been. Sure. So I definitely had a unique path. Mypast work experience had always been in sales, but I've always wanted to kind ofmove onto the marketing side of things. So after my SDR tenure, Imoved on to the MDR team, which is the end bound sal strap, in hopes of better understanding the Demenaga Gen side and marketing internally within ourown company. After being in that role, I moved into this role sales sequencespecialist, which it's helped tremendously that I came from that frontline experience ofboth in bound and outbound. So within our ORG I am responsible for creatingnew sales snippets, templates, sequences, really any content that the SDRs aregoing to use to help drive pipeline, as well as benchmarking content performance andmaintaining an organized system so that those frontline reps can find exactly what they're lookingfor. Well, it a cool roll and an important role for sure.And then, just lastly, last thing, I want to ask is just,in hindsight, kind of going through the experience of starting a s strfinding this new path at all. Happened really quick. What advice would yougive to yourself starting as nest are from...

...scratched you go back in time?If I could go back, I probably just really reiterate to myself that it'sokay to ask for advice and to help. It's totally okay if you don't knowthe answer to a question of prospects asking you or if you realize you'renot as strong on the phone as you are an emails. You just haveto align yourself with those people who are successful or that are willing to helpand coach you. So not only is that your manager, but of courseyour team leads and your peers as well. The more you ask, the harderit is for you to fail. Love very good advice. Awesome.Well, thank you so much, Megan. Really appreciate you jumping on and reallyappreciate it of course. Thanks Amy. Thank you so much to Steven,Roberto and Megan for sharing their experiences in their career after str our.Reach is actually hiring a lot of us yards right now, so if you'reinterested in an str role. Just go to outreach that IO and careers andapply the str role. We are hiring a lot right now, so canjoin us. This was another episode of the sales engagement podcast. To helpthis get in front of more eyes and ears, please leave us a shiningfive star review. Join US at sales engagementcom for new episodes. Resources inthe book on sales engagement to get the most out of your sales engagement strategy. Make sure to check out outreach that ioh the leading sales engagement platform.See you on the next episode.

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