The Sales Engagement Podcast
The Sales Engagement Podcast

Episode · 10 months ago

Don’t Rush Your Leadership Career (The Grass Isn’t Greener) w/ Rory Stern

ABOUT THIS EPISODE

You’re an IC right now, but you want to be in leadership.

You hear about an opportunity outside your current company… What should you do?

Recently on the Sales Engagement podcast, we had a chance to chat with Rory Stern, VP, Northern Europe at CybelAngel, about what it takes to plunge into leadership — and the best route to get there.

What we talked about:

  • Rory’s quest for financial stability
  • Amazing leadership role models
  • How to crush it as an IC
  • How to crush it as a sales leader


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

Welcome to the sales engagement podcast,this podcast is brought to you by outbreach the leading sales engagementplatform, helping companies, sellers and customer success engaged withbuyers and customers in the modern sales era, check out sales,engagementcom for new episodes, resources and the book on sales,engagement available on Amazon and Barns and noble or wherever books aresold. Now, let's get into today's episode all right, everybody welcome back tothese sales engagement, podcast, and if this is your first time attending, wewelcome you to the show. This is one of your host Alex cremmer. I am veryexcited. I've actually been looking forward to this show for a good amountof time I enjoy I'm joined here by the One and only sserory stern rory.Welcome to show my fiend thank you for having me of course, of course, manwell before we divin. I just want to kind to Gete a little background herewhere you and I had a conversation a couple of weeks ago, just about whathas been your journey. I guess you can say, throughsales and through leadership and through various types of companies andreally kind of growing them out to be prominent in industry leaders and justto kind of give a little background on on who you are and then I'll. Let youkind of give up more expansive opening, so you're, currently you're, actuallyyou're from e United States but you're currently living in London. You are theVPS sales for northern Europe at Cybel Angel, and you are growing at your teamthere. Prior to that, you had a long and successful career work, your way upthrough sales and then intusaes leadership at Yex, and you got a lot ofreally good stories here that I'm excited for us to hi've into so I wantto kind of open it up to you on. You know, give us a little background onwho are you? What do you do? What makes you roary? Okay, fair, fair, fair! Well, look very,I guess that's a very broad question in...

...general, but hey so I'm originally fromstouth Florida. I went to Arizona State Univerity for college and I I fell inlove. Studying abroad in Spain a pod graduation, I chased my partner back toNew York City, that's where she's from, and I took a job yxt within three weeksof Landi in New York City. That was my very first shob aut of college. Istarted at yext the first time around with Tomile and Dilan Callin smallbusiness owners making two hundred and fifty cold calls a day over six hours,a talk time of a day and just thaut that happened almost every day for twoand a half years there I did leave thex one to two different companies learneda little bit about enterprise sales in the meantime, and then because of thatthat allowed me to that have the opportunity to return to x in April twothousand and thirteen, almost exactly two years to when I left, while he asthe second time around quickly became one of our topic price sales people,but we sold to the largest businesses in the country I got stuck in on theculture. I was hooked in two thousand and sixteen they asked me to move toLondon to build out our business across Europe. So my partner Steph and I weldpacked up and we took the plunge four and a half years later of doing thatfrom startup all the way to an IPO. You know ten years in the books toy act. Itwas time for me to take on the next challenge. I was introduced to toAruana Karati over about a year and a half ago through a mutual connectionand the rest. If history and as if you said, I'm scaling out cybal Angel Across Northern Europe, butwe're growing pretty fast as we speak and we are the technological leader inthird party data, Leagu protection. So that's that's. You know where we aretoday. I love that I love that man well, let'skind of take it a little bit back here, because I think e there's a lot ofreally good information right there for us to kind of dive into even before Yex,even before Cywal Angel. I guess you know, sales is is an absolutelyincredible career and a lot of people...

...go into it for various types of reasons.Right. Some people have these big aspirations of driving the best car.Some people have these big aspirations of just being in the meeting where Ithe night, suit and selling. I guess how did you end up finding yourself insales and just on this epic path that you are on now yeah? I think it'sbecause, first of all, the reason I'm in it is because you know financially,my back was against the wall. When I came out of College F, I mean manypeople are in this country n in the states, at least in student loans.That's no secrets to the world, but I was that was youknow. Su lovs were easy.Yo Know I was in. I was in all types of debt up to my eyeballs, so financealldeat definitely put me there, but though, all all that said, though thoseare other things I was chasing thou to. You know you K, ow, being the guy whogot to be in the meetings. WHOAVE got to run presentations and salute andcell and really be a consultant and get into somebody's business and have aproduct that can legitimately solve a problem that was always exciting to meand also it was exciting to me to be the guy who does get tho host eventsthat the sporting events in the restaurants and and Golf Hav been all that stuff thatwas exciting and something you wanted to do growing up. You know I wasfortunate enough to see that my dad did. At you know my dad was t was asalesperson for, for my whole life, he was New York. Life Insurance is numberone agent in the world for the better part of a decade and looking back on itall, you know seeing him put on sutent tie on for the first fourteen years ofmy life day in a d day out to build us. This great life was prepetty awesome.So seeing that and seeing the Ligfe that you can build with that, Iunderstood the possibilities that sales can bring right now gain. I was tooyoung to understand the hardships that also come with sales to, but justseeing the the all the good stuff at...

...fourteen you know was amazing. You know insurancecompanies were doing presidents club way before you know. The tech industrymay have come to existence, so it was interesting to see that where he wasalways there speaking and all that stuff, so that was very cool so thattype of environment also. Definitely, I think, motivated me to an extent ofTwelv all right. So I love to hear that so your father, I love just kind ofseeing your dad put on the suit and tie every single day and just kind oflooking at that person's a metol be like y know. I could eventually dosomethieon those lives. Maybe it's not doing exactly, but it's definitely thepath that you went on. So how did you end up actually getting is in Tho Sales?I mean, I think, in our last conversation you mentioned right out ofcollege broke off your ass. You needed a job and you found yourself at yextand from my understaying it was a power house of a crew over at Yex. When youguys initially started an you. Guys are all kind of doing your own thing now ata very high level. But what would you I mean? What was it about that initialcrew? What was it about that leadership? That was there that gave you guys sucha great foundation to be doing what you are now. I don't know man, but wedefinitely did have a powerhouse crew, and you know we had a lot of great setlstown on that floor, Brian with Cosky, Brian Distel, Burger. You Know Brent,mets and Howard Larmin, obviously we're there as well, but brigter, Copski andBrian dister burger were the ones really bringing in you know the sales,the sales tocounty young sales toent and, to be honest, it was wild becausethey would hire you on the spot, so how coud they were just good atpicking at pick and talent. Also, we had a lot of referrals. You know, asthey got good people in. We all refer people in, but yeah R, there's.Definitely a group of us that we brought in we were trained by. You know,Briaakovsky very, very intimately. You...

...know he was our salestrainer. Our veryfirst tales trainer ind groups of six to eight. He is somebody that you donot want to disappoint, not because, like you're afraid of them just to youwas just that he was just such a good leader that you just never wanted atthisa point hem, so you just work hard and you listen to him, and you know weall competed t against each other and it was a lot of fun and we all stilltalk to this day almost every single day and to your point, we're all stillin tech, we're all in some way shape or form either individual contributors orleaders and SMB all the way up to to enterprise so yeah. We have that butyeah honestly, that's a question we ask out. We ask ourselves all the time, butwe aske them all the time. You know it was a hell of a group of people thatthey they were able to get together at such an early stage. Well, I think it'sany leaders dream to not just create a group hiring class that coal be likethat, but also be able to hire on the spot and Jo just be like you're, the guy oryou're. The woman who, I know is going to be a Badass here at our companywalking through Seso, you mentioned you know the leader there was sometong whoyou didn't want to disappoint right, someone who you want to make proud. Iguess you can say you know, I think, that's hard to find it a leader. Youknow at times, and somebody who you look up to not just as a mentor butalso someone is won't even say, like a father figure or even some the line,those sides. What did they do that you know helped? You say this is a personnot just cares that, whether or not producing revenue this person actuallycares about my well being right and who I actually am and become as a personyeah. I now that's funny, I think it Prodcostyo listes this and here's youreference of Father Rma a went too far there a little lit, but you tell meyeah- maybe maybe maybe older brother, but no Henow Rockcos, the man and nhe'ss a legend in in Obitch, saying...

...software sales, most people or been impacted by him, somewey SHAPperform for me early on ont ever for aget. Is he opened up my firstlegitimate checking account after college, so I was in so much I wasinsuch terrible. You know financial debt that you know I couldn't even get a checkingaccount anymore. You know I to Ol the story of my dad being incrediblysuccessful, but the same time around out fourteen years old it rapidly went away to this day knowme and my sablings. We still have no idea. The full story will never willand that's okay, a long time ago now, but at the same time, though, that thatperiod that made us all, you know so much more resilient, but we came with aa lot of uncertainty for a periods of time, financial and certainlydefinitely be a part of it. You know so when I got into to ca to yes aftercollege, I could literally not deposit my PaceLips, so Rukiovsky walking me over to Bank of America to work one day and literallycoassigned for me on my very first checking account so yeah so t's things like that, or youknow that literally new me for two months atthat point yeah, so he went with you to Bankmerica.He opened up your bank Yaud. I assume that at that point, you're like thisguy's got my back right. This guy is yeah and again that it's just at's sucha great story, a great example there, what it means to be a leader totallytotally Ragovski Y. U opitamizes pitimizes that, but I was veryfortunate to have to have lots of great leaders and lots of great examples ofthat in my career as well, but definitely- and you see the different- I guess the different shapes and sizesof that- the different flavors of leadership- and it's you know it's goodto have many many different styles. Well, you know you obviously had a verysuccessful career as an ine individual...

...contributor right. You mentioned that aExou end up being one on the top enterprise sales people there for agood amount of years. You traveld all across the country tree not just youing,very well, financially, but wbut. You were learning an incredible amount ofskeills of what it means to Notul, be a sales rep, but to really be a salesprofessional, and you know you mectione, that that was a big reason that now, asyou've, moved into leadership. You've been able to be successful and now getthe opportunity, like et cible, an angel to be growing out an entire UKteam. So I'm curious walk me through what did that journey? Look like ofmoving from the individual contributor into that sales leadership type of role.What were the questions that you were asking yourself? What was kind of themain driving force that led you there? So the main driving forced to lead meto leadership, I would say, was the move across the pond, while in thestates it wasn't something that was really thinking about or something Iwas chasing. I loved my life as an individual contributor in North America.It was amazing, it was everything that you know you and I just touched on andmore in terms of you know the being able to go to the events and and meetwith with really cool businesses an and help them truly solv problems.Meanwhile, earning jeurning a fair wage, so you know that was everything I wantedand then with the chance to move to Europe o learn a little bit more about different cultures and how you dobusiness across the world and really you n intimately getting involved inthe hiring where you know I yex I was. I was very heavily involved in hiringan early on in the early days, but they weren't my direct reports. You know,I'm saying it wasn't my team wasn't wasn't, wasn't wasn't the the team thatI was building, so all that was was was appealing to me at that point, and Iyou know. I think that if that was...

...offered to me in the states at the timeI would iave taken it, I'm not so sure, but the fact that it had you know theEuropean aspect of it. Wa was definitely appealing and I think thatyou know asking myselvs different questions. I don't know if I was askingmyself the right questions at the time, but I think that there are some veryserious questions. You have to ask yourself when you are stepping downfrom from an IC. You know, are you ready to make less money for a shortperiod of time? Are you ready to stop thinking about yourself? First, are youready to for for your satisfaction to not comeout of monstrous paychecks, but coming from building an organization andwatching people's careers grow not necessarily watching yours grow? So Ithink those are the questions that you defenitivly have to ask yourself aheadof time. Are you ready to give up your freedom? You know, and are you ready to essentially just it's a whole differentworld? Are you ready o start a whole new challenge, and if so, then, then Irecommend it. If not don't do it being individual contributor for the rest ofyour career is not the terrible thing at all. It's actually an amazing thingand can also be incredibly fruitful. I mean you make a really good pointthat so many people, myself included. Iremember right when I graduated college. I was like I want to be a leader. Iwant to be a manager if I can get there as soon as possible, I'm going to bestoked. I kneew that was kind of always my calling, but I remember one of myfirst, you know months of my job right out, ot a college. I had a Mentol, belike Hey Alex. I know you want to be a manager. You got to learn how to sellfirst tthere's, some things that you have to learn how to do set when you doget up to that sales leadership position, you're going to be a lot moreeffective there and you're actually going to be able to povide Vaalue tothe people on your team as well.

There's certain credibility that comesalong with that, and that was such a great lesson for me. It sounds like youkind of had that that similar type of experience of a first Lt, let's kind ofbust, my chops a little bit so to speak of learning this whole sales game andthen once you now are in leadership, you've actually been able to beeffective and leading, grow a team and also recruit and retain that team aswell because they say hey this is you know. Rori is probably somebody who Ican learn a thing or two from considering what is background yeah? Ithink I think that's, that's absolutely fair. I think that's one of the reasons I'm confiden as aleader is. I had this success as an I see. I you know to take an Americansports term. I stayed in the pocket for years, not one or two sales seasons,but you know seven or eight sales seasons. I stayed in the pocket, Icarried a quota. I know what is required to be successful right and Ithink that goes a long way when you're leaving people into the same exact jobthat you've done in the past. It's not as easy to lead people when you haven'thad that direct experience for years right. If you haven't felt what theyfelt it. I think it can be very challenging to be the best popibleleader, so I'm grateful for that. I also think that there's another thingthat being isee Dhos for you and you know, there's a little bit of financialstability theme here, but financal stability as a sales leader issomething I think your ises want you to have you know if it's raining on you, it'schallenging. If you're back to the wall and your commission check thecommission check yourself, it's probably a little more challenging foryou to protect your salespeople, which is avery important thing. So I think, there's a few things that come withbeing an. I see that, frankly, either people are rushing toget away from, maybe they're, maybe they're afraid of missing quota and ifyou and if you have a Qoda and you miss...

...it well, then maybe you're not going toget that chance to promotion right. So I think there's also that fear peoplehave it's a survival game and for for many people, so I think there's a fewdifferent things. You know we could talk through on that,but at the end of the day being- and I see serve me incredibly well, for myyou know- life and leadership today, hmm, I really like what you said rightthere around. You know certain ICS want to move to leadership because there's afear of missing quota right, and maybe that hits me like Corin my stomach ensebeecause, like I know that year, I remember being the I se and be like Igot to get to I'm excit you two leaderships, so I don't have to havethese feelings every more, especially when a new month comes around, nomatter how good you did. Last Tim, it always starts at zero. Again H, at's,not an easy feeling right, that's not, but the funniest part is, is likeyou're rushing to get out of that that quota, because you're an IC but you'reonly going to a bigger numbers like if you think you're going to go toleadership and not carry a number, then that I don't know what type ofLeadership Oroll that is in a sales organization, the least- and you know frankly, if that number's notgetting bigger, because you're stepping into a leadership roll who are youleaving? What are you leading? You can't get away from a number thatdoesn't exist on the sale side of the organization. Well, let's kind of askyou two questions here and it's going to be on. You know two different sidesof the coin here in terms of being an IC for the various ices that are listening tothis podcast right now that are listening to hom, like okay seems likesomeone who was very successful whet. He was one. What do you think it takesto actually be a successful aisee in and this? This is a loaded questionhere, so I'm first off agnology nowways, but you know what would you recommendto people that are in that in that same...

...situation right there that maybe havean inclean of being a say leader eventually, but are still in this ICrole? What do they do? Tho Double Down on the lessons that they're named tolearn and succeed right now, and I would say that, if you're in an ICCrole today that you need ey focus on doing your job, I know that is a clicheat this point, but really understand what you're being measured byunderstand what you need to drive: Pipelin right, Pi, blime generation,right at the end of the day. That is what we're doing you have to understandthe funnal fear specific business so to know that, okay and understand how youcan contribute to that, don't be afraid to pick up the phone don't be afraid tocold call. Okay, that's obviously the fundamentals, but that can never besaid enough. Another aspect of what you need to be in to be successfulresilience. I think we all know that you need to you need to want to great.You need to want to be curious. You have to be curious.Asking questions have have a lot of energy that those are all lot of theintangibles. But then you also have better learn your product right. Takethe time, learn your product. Okay Ring People into your deals. Right, you arenot. Sales is not a one man's sport anymore. There are an especially insoftware sales. Bringing leaders around you and ask for feedback, be coachable.Okay, your manager wants to work with somebody who wants to learn. Ay, neverstop. Learning, that's Ome, the advice I would give to somebody today, O'swho's in and Icee, and then don't lose the force through the trees in terms ofyour career path, don't rush into the very first recruiting call that you getto be. You know a leader somewhere else: okay, realizethat if you're in IC had a good company, you like the leadership you like theproduct you're doing well, that's...

...probably the best place for you to takeyour first step in leadership. You know I really like what you said right thereas well. I feel like when, like like understanding your prodt right and Ithink that's so underrated, or at least people assume it or don't talk Lotivery often, but if you know your product or your service very wellyou're going to be credible, you're going to bee a expert in your field,but even kind of going back to you know being a sales wreck. I think theimportant thing to be able to do is: can you build a framework of skills,whether it's, how you frame conversations, whether it's, how youlead someone down a path of discovery and asking for impact and metrics,whether it's negotiation tactics or whatever it might be? If you can learnthose frameworks, those repeatable tolk tracks there and then it's just amatter of inser product or service here. Those are the intangibles that when yougo on to your next role, whether it's as an IC or as a leader, you can trustand you can have the confidence that I'm going to do well here. I just needto learn the product, but I know what it takes an now. The frameworks that ittakes to succeed here, I'm curious: Does that land with you or do? Is thatso that you believe it or you teach your tm as well yeah. I know absolutelyone hundred percent, you know at yecs we were lucky to go through forcemanagement training. Obviously you know that's like one of the gold standardsand software training and that's kind of like the basis of that salesphilosophy. It's not necessarily selling. You know what you sell. It'sit's! How you sell it right, it's not it's not what the customers buying it's,how they buy so yeah. Absolutely. I completely agree with that and a lot ofthose intanisibles s are those qualities that will serve you for forthe rest of your life. You know things like just that, curiosity, that andenergy and the hunger to be the best.

Well, let's, let's kind of look on theother side of the coinment, so we talked about what it takes to be a topAA top IC. What do you think it takes? Exy succeed as a leader I mean you, I'm super jealous of your position. ToI mean the fact that you just move out to London, you grew out the me officefor Yext, now, you're growng out the Amia or the northern Europ office,forcyvl angel. What does it take? How do you actually get these opportunitiesand what s e to succeed as a leader in those rolls so to succeed in as a leader? It'sdefinitely a different, a different set of tools. I think you know you have tohave all the qualities that we mention above. You also have to know how torecruit great talents and what that looks like right. Additionally, I thinkthat there's a certain level of patients that you have to have againI'll say it again. I think financial stability helps sales methodology. Youknow you have to be flexible because not all sales nothiologes or onesizefits all, but I think it's helpful to at least have some generalunderstandings and at least be an expert in one and then you know, andthen again I think you know motivations is the hell of a drug, and I think atthe end of the day, what is it that motivates you? So you know, as an I see,my motivation was always to get to that financial stability to make sure that Inever did. You know made similar mistakes that I've seen in my pastthrough my family, and that me and my part, er staff. We have you, know afinancial freedom, francial stability that was always my driving force andnow it's less superficial, my new driving force and what kind ofmotivates me it's I really enjoy. Watching people grow their careers, areally enjoy building the business and, seeing you know all the differentpieces come together. So I think you know a big piece of this is that has tobe something that really really gets. You excited and you can be passionateabout. If that doesn't then again, it's probably not the theroal for you.

Well, I think I think you make aphenomenal point right there. It's no longer about just you. I think that's the biggest iinfactor Imean you know if you lead a team of you know six, eight, ten, you no whateverit might be. You know you're there to support themand make sure that hey not just how they draging revenue and hitting quotatlike at times you're acting therapist at Oh yeah, your motivatinal speaker atat times you're talking about their personal life as well and supportingthem there and you have't to wear a lot of pats you having to be a supportperson for people in ways that you typically would have to be a an thattimes. That is like, I feel uncomfortable, but I need to show upfor this person right here. Absolutely that's tis Haman! Well, I love these these topics ar hereI love here and what it takes to be a top IC. I love herind what it takes tobe a top leader as well a few more questions here before we kind of letyou go back to r your day to day life, and you become famous from doing thispodcast here growing a team in a MEA. I got to askthis question. It sounds unbelievably exciting. What is that like? Like you're meetingpeople from you, know tons of different countries? Everybody has theirdifferent cultures and just different things like that. What is that like?How do you actually do that? I wonder some of the challenges that you've beenfaced. Ing Doing that. So you know what it's like to build. Ateam across Europe is just is a ton of fun and that's what really excites meon a dayto day basis is interacting with people all over the world, so youknow there's a lot to learn, though right as exciting to your point. As yousaid, it was 'n fun as it sounds. You have to learn all the local rules andregulaations. You know all the difference. You know how to hiresomebody, how long somebody before...

...before they leave your business. Whattype of notice do they have to give you, or do you have to give them? We have tolearn about? You know also all of the different driving factors to what makesthem tick and based off of you know, different countries. You learndifferent things about people, different cultures and it really isfascinating and there's there's a you know. Look, I think, there's an aspectof it too. That you really get to see ticket American sales approach,which I think people all over the world. You know know that we as Americans, weare proud sales, people and youryou're realizing, that's not the caseeverywhere in the world. I there. I think there is a bit of a stigmin. Icertain parts of the world, not everywhere where you know, if you are asales person, there's definitely a little bit of stigna that comes with itso ju. Seeing that F. That point of view, too, is alsointeresting interesting. I never thought about that. There is adifferent stigma or energy towards salespeople in the US versus in Europe,and I totally feel at it and then it can understand that vow, but I neverthought about that. It's very interesting, absolutely an I think forthat reason that it's, it also does make our talent pools smaller in Europe. ToAn extent I mean, obviously it's smaller in general, but even per capita.I think our TALENTFOL was smaller yeah. Well, I guess that just means you gotto be a better recruiter than Ha. I man well Rori, I'm not gonna lie man, thishis been awesome. So before I asked You my last question Yere, I just want tohonor it and acknowledge you. I appreciate your authenticity of showingup here walking us through a little bit of your story. Watchyour Dad grow upcause Om the difficult times your your family experience and how that Shakedyou to be what you are now and the Opportunis that you got early on inyour sales professional career, the...

...manager, the mentorship that you wereable to get. I think its just such a great lesson of for all those peoplewho are leading teams right now. The impact that you can have on your peopleis so much greater than just ensuring that they're hitting quota right,you're helping them become. You know the mature adult so to speak, that theycan be, and just to hear your experience of what you've done fromthat working up: INTI leadership, nobuilding out varioussesive teams, Gointo the UK and just the impact thatyou're having right now, man, your Stori's awesome and I'm excited forpeople to be listening to this today. So last question for you here- and thisis my typical question- that I always ask everybody who's on this podcast,and it is this if you had to impart one piece of wisdom across all of ourlisteners here whether it is in regards to what we discusse so far in thisconversation or something completely else. What would that one piece, Owisdom, be don't rush your cer path, don't look atyour time as an individual contributor as a sentence right as a jail sentenceright, look at it as a some of the best times, you'll have in your professionalcareer, look at it as a actual profession and don't feel like you haveto fush out of there into the very first leadership opportunity presentedto you. I think that is definitely some ways in that. I'm sure people get tolda lot, but it's it's true. So if I could leave in one piece that would beit don't rush your career path, the grass isn't Gre Ilove it. I love a Mani, will worry ifany of our listeners are interested in getting a hold of you or interested.Even the plan for the jobs that you guys have over there in the UK, what isthe best lay for that to get a whole yet absolutely linked in man. Roary Stern,please feel free to connect. Hish Mae...

...would love to hear from Yiu the one andthe only ray stern. Well, Hey Rorr appreciate you be ons podcast and forall of our listeners. Thank you once again for joining the stills engagementpodcast. This is one of my favorite things that I get to do within my dayto day just learning from awesome people like yourself Fori, so thanks somuch and have an absolutely awesome and go crast your day. Thank you. This wasanother episode of the Sales Engagement podcast join us at sales, engagementcomfor new episodes, resources and the book on sales. Engagement now availableon Amazon, Barns and noble or wherever books are sold to get the most out ofyour sales engagement strategy, make sure to check out outrage. The leadingsales engagement platform see you on the next episode.

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