The Sales Engagement Podcast
The Sales Engagement Podcast

Episode · 1 month ago

Career Transition Mistakes & How You Can Avoid Them


It’s not every day that you find a successful person so willing to openly discuss their mistakes, so that you can avoid them.

Ben Rogers, CMO at Travala , is one of those rare finds who recently joined me on the Sales Engagement Podcast. 

In this episode we discuss:

What to expect when transitioning from a corporate role into your own startup

Which advice not to take and what to replace it with instead

How Ben fosters a growth culture at Travala

The mistakes that Ben made and how you can avoid them

Check out these resources we mentioned during the podcast:

Extreme Ownership: How U.S. Navy SEALs Lead & Win (a book by Jocko Willink) 

For more engaging sales conversations, subscribe to The Sales Engagement Podcast on Apple Podcasts , Spotify , or 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 podcast.This podcast is brought to you by outreach, the leading sales engagement platform, andthey just launched outreach on outreach, the place to learn how outreach welldoes outreach? Learn how the team follows up with every lead in record timeafter virtual events and turns them into revenue. You can also see how outreach runsaccount based plays, manages reps and so much more using their own salesengagement platform. Everything is backed by data pulled from outreach processes and customer base. When you're done, you'll be able to do it as good as theydo. Head to outreach Doo on outreach to see what they have going on. Now let's get into today's episode. Welcome everyone to the sales engagement podcast. Thanks for joining today's episode. It is your host, Caitlin Kelly,the senior manager of sales development at outreach for the Amia region. Alongside me, we have been rogers, CMO at Travalla. Super excited for today's episode. We are actually going to be diving into transitioning from the corporate world intoa more startup environment, embracing the change along the way, and then also, coming from someone who was in the travel industry and then transition and pivotedthroughout the pandemic. We're going to talk about a lot of the mistakes thatwere it along the way and things that that Ben has learned in his TMOrole at Raralla. With that being said, Ben I'm going to pass it overto you to give us a little bit of insight into what you doat Travalla and a little bit about your career path. Yeah, wonderful.Hey, Kevin, thanks for having me here moving forward to this. SoI'm not looking forward to actually tell you out some stuff. So, yeah, some things I stuffed up rather than things that are going well. It'sa nice change getting to, you know, be very rare, reverent and honest. Yeah, look, you're right on the money. Yeah, Iam the chief marketing officer of TRAVELLACOM. If you don't familiar with us,we are a travel company that accepts crypto in a nutshell, and then wehave our own talking as well to that. That is effectively our rewards program andthen, if you other use cases there for that one. We havethree million plus travel products on our side that self service bookable and we alsohave our luxury concierge as well, where we're helping to take care of thata top tier in the market. Just that meant done maybe very well incrypto and really looking to sort of rap those rewards. So I think thatwas a second part to your question. There was a little bit about youryour path and then how you got here. I was a yeah, so Iyou're right about our four years ago I was in a very sort oftraditional corporate type career path. Hated it, was very unhappy, did not likeit at all and I did transition into the the startup world, andso I had my own business, a couple of businesses actually that that cascadedout into. Both of them kind of grew. One of them, youknow, as a sort of a few months ago, officially is is verymuch a retool now, like we've licensed him software rather than having our ownand you know, it freed up my time a couple of years ago tosort of come help out the the this business that I'm in, Travelat tocalm as well and and grow. So I made plenty of mistakes. Ididn't properly prepare for that transition at all and I guess we're going to talkmore about that now. Fantastic. I am looking forward to hearing about themestizing you made, coming definitely from like a more structure background, having thatdip into entrepreneurship and then jumping into the travel industry. You know, alongthe way. What how did you really embrace or I guess, what wasthat transition like, coming from the corporate world into the startup environment? Whatwere some of the biggest differentiators that you had to adjust to? The biggestdifferentiator is, I suppose, not having...

...a paycheck. You know, whenyou're out there working for yourself, you know the no, someone's not justputting money in your bank account all the time. So you know, youreally do have to probably believe in yourself and what you're doing if you're gotto be able to keep going and learned, learned to kind of struggle and learnto get by, you know, for some time with, you know, perhaps fole less than what you would previously. So so it is rough. Also, you're going to lose a lot of people, just to bevery honest, you will. You're going to gain more, a bit differentpeople. Bach going to lose people. You're going to be a bit ofa freak. You know people like to talk about what their job is,particularly it's small talk and where they work, and then when it gets to youand you're explaining some things you you start to be a little bit ofan outsider, very much so so so personally, these things are going tohappen a lot. Also in a corporate environment. We got to paycheck.You know, you're run, you're on a team, you're very kind ofsheltered from lots of things. So what. But I think I'm trying to saythey're a bit better is you go from maybe performing a particular task or, depending when you are in an organization, a couple of tasks, to basicallyhaving to do everything. You got to go to run the books,you got to market, you gotta sell. Anyone who's in tech and is encodingto some degree, you're kidding yourself. You're going to roll up your sleevesand learn how to Dev you've got to do it all and do it, I sorry, learned quickly and then also, like it, get getto a point that you've got something to sell very fast. was there anyI guess like, was there any resources that you leverage to really embrace thischange or kind of speed along the learning curve that you were in during hmm, that's that's such an interesting question. So I did, and it's interestingbecause I did utilize a lot of resources and in hindsight, I probably shouldn'thave used utilized a lot of them. A lot of people are going togive you advice and be like, you've got to go to this startup thing, are you got to go to that networking thing, you got to watchthis video, you've got to go out and find a mentor you gotta likegrow a team. Like every every man and the dog is going to giveyou advice and some of these people do seem quite credible as well too,with with their careers or they're rat you know, as a start up huband these things. So in the early days, if I was looking backon a right now, I would have gone to follow less of those things. I actually would have got sort of a probably would have gone for afast, smaller sort of opinion and really sort of like lent on, youknow, a lot more books, a lot more audio books from people thatare perhaps out of reach, because that's really where you kind of want towant a head to. But the biggest thing, I would say is justfocus on your product, focus on your you know, your market, anddo it. You know, and then a lot of these start up thingsin these places, they're going to tell you got to go get a tshirt with your brand on it. You know, you got to go kindof be like what you yeah, that's little TV show. I think it'swhat sillic in value or something. You know, you gotta go kind ofplay the the cliche. But yes, yeah, no, I think there'ssomething to be said and I think a lot of people get wrapped up inthe training and the edgy, which it is all important, but you're actuallygoing to learn by executing and learning in the middle of it all as youare doing it. Well, how we're gonna love like humiliating yourself. That'sit is crash and burn a little bit. Kind of lean into the failure there. So kind as you were going through this transition and a lot ofpeople aspire to do some career path similar to what you have been able toachieve. As you are, you know, leading the team over at Travalla,how are you creating a culture that is, you know, we're failureis encouraged for them to grow. Yeah, so what I would argue here isyou really need to communicate the goals very clearly of where you're going andhold people accountable to their path on that goal. And our goal is verysimple. It's always to make more money. Make more money, spend less money, you know, increase that that kind of gap there and being insort of the marketing or I've even thrown that word away like I like touse the word growth, because that's effectively...

...what we're trying to do. We'retrying to grow the business and there's there's so many ways to do it.So I keep everyone focused on and we have we have a weekly meeting,for example. All I want to hear about, all I want to letyou brag about, is what did you do this week that actually led togrowth? I don't want to hear that you know, you had to dothis operational task, this or that you I just want to hear what youhave for growth. And you know, it's been quite effective because everyone hassomething to bring to that meeting now that we have there and we make everyonereally well on the on my team, really well aware of the the situationthat the business is in, what's going on. It's almost sort of brainstormingand we're coming up with ideas. They're relevant to our situation and I wantto leverage them. I just want us to all work on the best ideathat's going to get us to where we need to go. I don't mindand who it comes from, as long as we're doing it. And theother rule I have, as well as focus on growth, is when you'recoming up with ideas, come up with ideas that you can execute right.I mean so many people have wish lists of things that they flick over toother people in other areas the business to do and they they but you knowwhat, it comes time for them to drill down and actually, you know, jump in into the work, they're not so keen. So we reallyencourage that as well. And it can be something like I really want todo this bit. I can help project manage it, I can help planet, but I need this part with this or I don't quite know how todo this. Can you help me learn that? Or what are the resources? Or I think this thing I need to learn is within my grasp andit's going to be beneficial. So I'm not saying don't do anything that youhaven't done before, just you know, kind of know what you are ableto do get there, and then that makes my job quite fun because Istart to see the abilities of the people that we have on the team.Then I can push them a little bit more and, you know, andget them believing in themselves a little bit more as well too, and itreally really does have a pretty powerful impact on our growth. Yeah, Ican imagine. So a lot of a lot of the things that I herepretty often are is like how to make these meetings more efficient, and soI love how you are seeing keep it very simple. It's like, howhave you impacted the growth of Dralla? What have you been able to execute? Which is super simple and it probably provides a lot of clarity for yourteam on the back end of I have you been able to see this drivelike a efficiencies within your medians, but also has your team been able toexecute their roles? Yes, it certainly has. And then time amount efficiencies. I had a meeting to this week with with with one of the teamand she's asking me for permission to do something and I'm like, Cook,what you're asking for permission for? You don't need me if you know thisis going to lead to growth. Like it does remove me for that conversation. Go get it set up, go get it done and then next timeand in future we catch up on these things. Say Hey, been lastweek, I did this, this, this, you know, like ifif it's within your grasp, between your reach, get it done. Sowe'RE WITH IN TERMS OF EFFICIENCIES. I'm removing a lot of stakeholders. I'm, you know, and unnecessarily sort of checkpoints and approvals. It was putsomething like this to me, like we're not saving lives intact. Right,we're not saving lives, you know, like we're not doctors, we're notsurgeons. When someone makes a mistake, you know, no one dies.You know, worst case scenario that's going to happen is you know and youknow you might lose your job. That's like literally the worst thing that canhappen. The realistically most worst thing that can happen is a website might godown. So the stakes really aren't that high. So if you're coming intostuff with good intentions and you know what you're doing, I really say gofor it and then, you know, we'll chat about it if something's notquite right afterwards. But I'll never get angry at someone or be disappointed withsomeone for trying to grow the business. Yeah, that's easy, and Ithink the environment that you are creating there is probably extremely empowering and allows peopleto take ownership of different initiatives and of their roles as well, so theyfeel like they can actually execute and drive the growth for you without feeling theyhave to get approval on everything, which...

...ultimately could cause a lot of roadblocks along the way. So previously we had talked about you said, youknow, if you transition for that corporate world and you go into like thisentrepreneurial ship phase, you have to roll up your sleeves. You're going tobe wearing mini hats along that process. Along your journey, been able todevelop quite a array of unique skills, and one of the things that wewere going to talk about today are what we're some of the biggest mistakes thatyou have made in your early stages or things that you would have done differentlyas you look back. Oh, okay, yeah, yeah, into the goodstuffs, into the good stuff, the good stuff my way. Whereshould we get started? I like this is feels like therapy to get somestuff off my chest. I think I'm the big let's let's look back onlike when you were first hiring your first team. Let's talk about any mistakesor any advice you'd give to anyone out there who is about to embark onthe journey. Yeah, yeah, first thing was is I was I wascheap. You know, you're watching the pennies in the early days, there'snot much of a difference between like your money and a companies money. Youknow, it is is sort of the same money if your boots trapping,and you know, particular if you're a first time entrepreneur, I like me. So when you're looking at the bank, at count you're thinking of that,that, that's that, that's your money. So I definitely wasted alot of money by buying cheap people rather than getting experts. I wasted alot of money by hiring people who I thought had potential that could be,you know, improved or wanted to grow in this but we're cheap. Andthe biggest mistake I made the two mistakes I made their first of all,I wasn't hiring people who to do jobs that I couldn't do. There wereof a similar skill set to me that we as a business would be ableto go together. But the second thing I assumed that everyone like thrive forsuccess in life and that would everyone's sort of like thrive for success. wassimilar to what I had defined success out as well too, because you're havingthe the conversations of sure Evan's had. You know, give, give outa little bit of equity. This goes somewhere. You know this is goingto be really cool and exciting and although you know you'll get that persona backin front of you, you know when they're going home or thereof they knockoff for work. You know their headsets in a really sorry their head spaceon headset, their head spaces in a very different place to where I amwhen and sort of I'm never kind of turning off and really pushing. Sothat was it was a pretty, pretty big mistake there. Also in termsof hiring. You know, it's firing people that you've hired, that you'vepaid. That was toff. I should have fired a lot more people.I let of a lot of people that were not succeeding, struggle for along time and it really brought down the business. The cultural problems that itcreated were catastrophic and take a very long time to correct. themselves. Imean it wasn't the first time I've had the fire people. You know,I've fired people in the corporate world, but it's normally been like here's youbudget, someone's got to go. So it's like, Hey, it's notme. You know, I like I can kind of give myself's not howI do it, but I kind of give myself that little monolog in myhead here. It's like it's yeah, it's a hundred percent your decisions thatyou're getting into, but then, at the same time, by not makingthat decisions, letting people struggle and flounder, etc. You know, the businessisn't growing, you're not moving for while, you're not moving forwards andyou're ultimately shooting everything in the foot. So that's what it would come aroundto with hiring. Now, you know, I'm very much a big advocate of, you know, like all those those cliches, like Steve Job said, you know, hire people smarter than you and tell you what to do. You know, I'm all about that. Now. I really sort of whenI when I interview people, are like to get to the crux oflike what does success mean for them, and some other things you do aswell to as you do have mental health problems. I, like everyone hasmental health problems that come into to this and something that don't know. Imeant that. So everyone has mental health problems in general. Not everyone who'sin start ups of mental health problems. I mean they might. I don'tmean darted to prove that. I won't get down that, but you knowit. The startup communities, they do attract a lot of people who itis a friendship circle and it is kind of like a culture, well sometimesfor some people who are a bit of...

...outsider. So you do pick uppeople that perhaps don't have the best support networks and stuff in their personal livesand they need to kind of lean and on that. And Yeah, thatobviously has its has its own struggles. So I think I made almost everysingle mistake you possibly could make with with hiring people. The only thing Iwill say is everyone that we did hire was was always ultimately really nice people. Very honest, is as honest is wrong with never stole, if youwill, but they were all sort of good people. Yeah, okay,fantastic. So you were hiring really nice people, but along the way youryou would have shot a little bit. You would have invested a little bitmore money into that, into the experts, rather than trying to develop from thebottom up. Absolutely, and, you know, we do still havesome people with us who, you know, did come from, you know,the old way of doing things and they really sort of push themselves andthey had a suppose, a closer definitions of what my success was to me, but they were, you know, they were the Unicorn, they werethe the they were the exception to the rule. And again, I learnedthat the hard way. What would you say, as you're kind of buildingthe brand for either your own companies that you started or for Travala, whatwere some of the mistakes that you'd meet along the ways you're kind of likebuilding that Britain. Is there anything that comes to mind or that you havedone differently? Yeah, hundred percent. Not Talking to people, not talkingto your customers, trying to lean on things like ads or social media oremail automation or any of those like hot topics rather than going out and literallyknocking on some doors and having discussed with people about what they want, whatthey need and trying to sell stuff. That, ultimately, is always themistake. I've developed a saying like from it is like I would rather sellto one person then I would to tend people. I'd rather sell to tenpeople than a hundred, a hundred to a thousand, because it's about thethousand mark that you really need to you can't be having one to one conversationsor really get a proper feel for what's going on. But in those earlydays, or it's a new product or it's it's something that we're changing,that we added activities to travel at a calm for example, it's not untilyou go out there and you start talking to people about what do you need? How do we get this across the line that you're going to really reallysee some growth with that vertical was there a like a process that you putinto place to make sure that you were kind of building that report with yourwith your customers, as you guys were continuing to grow, or is itjust being more conscious along the way? It's been more conscious. I thinkyou know there's people are also random, right, and what you're doing canbe so random. So it's sometimes real tough to to be say you youhave to do this, this, this, this, this, see a beingconscious, I think, is a fantastic word, and sometimes you literallydon't need. It's just common sense. Some stuff it's ultimately common sense andyou don't need lots of data or lots of verification for it and it justworks. But there are other times you need lots. Yeah, I wouldsay never stop listening to your customers and always change your questions. Like Ialso notice people will start to tailor questions for certain answers that they get andthey can miss details when they're they're talking to people as well. So beconscious of the the feedback you're getting, but also be conscious of the feedbackyou maybe looking for and be a little bit of reverent with yourself and ifyou get bad, get so use sorry. You'll know you're kind of leveling up, I think as a marketer, of salesperson or everything, when you'vehad so much well, you've put your heart out there, you put anidea out there and it's being beaten up so many times that you don't feelthat anymore, because then you realize reach this kind of self actualization phase whereyou can just ask things and you're not going to take it personally when maybepeople don't like it. Yeah, that's a big skill to that. Alot of people it's hard to develop that skill not to take things so personally. But, as you mentioned, if... get to that point where youno longer are, it's probably because you've done it so many times that you'rejust you accept the feedback and you keep on marching along. Absolutely, andI look some people and naturally better at not caring what others think. I'mnot one of them, so it took a long time to for me andthat's it. Everyone's different as well. But yeah, again, I'd putthis as like an example WID talking about before with the team. Is Ifthat's the destination and that's the goal, you know reach this point that youdon't take it personally and everyone's there, that's the North Star and that's whatyou can kind of optimize yourself or your team to. Woods. Yeah,so I just like the third thing. When you're thinking about as your buildingand scaling Travalla and you're developing your team internally as well, as you lookback, was there, was there anything that you would do differently as youkind of car about these careers or inspired people that came into your company tothrive? Oh Yeah, Oh yeah, and captain, hindsight is such anamazing thing. When I came into the business, it was sort of withas a merger. That's why I joined. I came from a company called travelby bit and they were travelacom. was sort of a big change.The company's size increased quite a lot. They were going from being like areally sort of flat structure to having some more higher archy and and these thingsto it. We do have a large part of our team in Vietnam aswell. I didn't really understand the culture of their work environment that they're inor how things had worked before. I really tried to push, you know, sort of like what I wanted, probably a little bit too hard withoutunderstanding the the circumstances in the situation that was there. So yeah, youknow, and I kind of broke my promise. I sort of initially saidto the guys when I came in, look, I'm not going to saymuch for the first month. I really want to observe things. But thenI spat like day for I started to say things and kind of missed outon that opportunity to fully understand the business that I was stepping into and theway these these guys were working. Having said that, you know the thereare some positives to it, you know, like conflict can be good and shakingthe barrel and changing expectations and exchanging standards of things can be a goodthing, and I'd love to say that, you know, I had fully plannedout what they was going to look like and it was a fully calculateddecision on my part with a lot of Intel. But no, it wasn't. I started rattling some bushes very quickly and that maybe with some people createdalong the journey for me to help get them to where they need to befor the business to grow at the rate that we are right now. Thatthat's really interesting that you'd mentioned that when you first came, when the murderit happened, you were going to lie yourself a couple months to really understandthe cultures. From one month. One month. Okay, yeah, Iwas getting to my question. was going to say, what is it?What is the appropriate time? Would you say if somebody was an in yourposition? Yeah, look, since the next time I do something like this, I'm probably going to say I'll stick to the month, but I'm goingto be sort of aware of it. You might not have had the opportunitywithin a month to fully experience like enough Dev cycles or you know, there'sall sorts of things that can happen for how that culture works. There's goingto be layers of layers. You know, on boarding something or someone into acompany takes a long time and the further down the road that, sorry, the further along a company is, that, the longer that that takes. I don't think you want to take too long, particularly most people havea probation period and if you're really kind of sitting on your hands or kindof running at fifty percent, that's probably not a wise career decision. ButYeah, look, I would say a month, but be be conscious tomaybe extend or, you know, you might be able to shorten that.All right, fantastic. Well, love all the insay that you've shared.It sounds like you've had a lot of learnings along the ways and a culturein the environment that you are developing over a Tra rolla sounds like something veryencouraging in empowering to be a part of.

If you had to recommend one bookthat the biggest impact on your professional development, what would be like thatone book that you would recommend listeners read? Yes, sort of one of thebooks that help make me decide that it was time to quit the corporateworld and and go down this new path. It's extreme ownership, one that comesup a lot, I'm sure if you it's it's by a navy seal, or Xnavco, called Jocker, and he now has a consultancy firm wherehe will help businesses to lead effectively, to take leadership, and he putsup against scenarios, against time and war. So basically, so to be like, I met this CEO, he was having this problem, thought itwas the end of the world and then the next bit'll be like a remindedme out this time that I was like in Iraq and, you know,we were under fire and all these things. So really put stuff into perspective andI just like the notion that, you know, you can take extremeownership of your actions and the direction that you want to be. So yeah, would be that book. All right, so extreme ownership by joco drop Jacko. Will it fantastic? Well, thank you so much, been forjoining us today and sharing a lot of insight on a lot of the mistakesthat you've made along your career path and embracing changes as you've gone from thecorporate world into the startup environment and especially in the travel industry. If anyof the listeners wanted to follow up with you, what would be the bestway for them to reach out? Oh, twitter or being an encrypto and bigon they twitter's pretty big. So I think it's at Ben and Rogers. Also, you could probably find me on Linkedin as well. Been Rodgers. There's a few of us, but on the one wearing the blue shot. All right, fantastic. Well, you heard you heard it here first. Thank you so much been for your time today and until next time everyone. Thank you. Thanks, Kay. Look, this was another episode ofthe sales engagement podcast. To help this get in front of more eyes andears, please leave us a shining five star review. Join US at salesengagementcom for new episodes. Resources in the book on sales engagement. To getthe most out of your sales engagement strategy. Make sure to check out outreach.That ioh, the leading sales engagement platform. See you on the nextepisode.

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