The Sales Engagement Podcast
The Sales Engagement Podcast

Episode · 6 months 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, and they just launched outreach on outreach, the place to learn how outreach well does outreach? Learn how the team follows up with every lead in record time after virtual events and turns them into revenue. You can also see how outreach runs account based plays, manages reps and so much more using their own sales engagement 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 they do. 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 into a 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 pivoted throughout the pandemic. We're going to talk about a lot of the mistakes that were it along the way and things that that Ben has learned in his TMO role at Raralla. With that being said, Ben I'm going to pass it over to you to give us a little bit of insight into what you do at Travalla and a little bit about your career path. Yeah, wonderful. Hey, Kevin, thanks for having me here moving forward to this. So I'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's a nice change getting to, you know, be very rare, reverent and honest. Yeah, look, you're right on the money. Yeah, I am 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 we have our own talking as well to that. That is effectively our rewards program and then, if you other use cases there for that one. We have three million plus travel products on our side that self service bookable and we also have our luxury concierge as well, where we're helping to take care of that a top tier in the market. Just that meant done maybe very well in crypto and really looking to sort of rap those rewards. So I think that was a second part to your question. There was a little bit about your your path and then how you got here. I was a yeah, so I you're right about our four years ago I was in a very sort of traditional corporate type career path. Hated it, was very unhappy, did not like it at all and I did transition into the the startup world, and so I had my own business, a couple of businesses actually that that cascaded out into. Both of them kind of grew. One of them, you know, as a sort of a few months ago, officially is is very much a retool now, like we've licensed him software rather than having our own and you know, it freed up my time a couple of years ago to sort of come help out the the this business that I'm in, Travelat to calm as well and and grow. So I made plenty of mistakes. I didn't properly prepare for that transition at all and I guess we're going to talk more about that now. Fantastic. I am looking forward to hearing about the mestizing you made, coming definitely from like a more structure background, having that dip into entrepreneurship and then jumping into the travel industry. You know, along the way. What how did you really embrace or I guess, what was that transition like, coming from the corporate world into the startup environment? What were some of the biggest differentiators that you had to adjust to? The biggest differentiator is, I suppose, not having...

...a paycheck. You know, when you're out there working for yourself, you know the no, someone's not just putting money in your bank account all the time. So you know, you really do have to probably believe in yourself and what you're doing if you're got to be able to keep going and learned, learned to kind of struggle and learn to 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 be very honest, you will. You're going to gain more, a bit different people. Bach going to lose people. You're going to be a bit of a 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 you and you're explaining some things you you start to be a little bit of an outsider, very much so so so personally, these things are going to happen 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 of sheltered from lots of things. So what. But I think I'm trying to say they'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 basically having 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 encoding to some degree, you're kidding yourself. You're going to roll up your sleeves and learn how to Dev you've got to do it all and do it, I sorry, learned quickly and then also, like it, get get to a point that you've got something to sell very fast. was there any I guess like, was there any resources that you leverage to really embrace this change 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 interesting because I did utilize a lot of resources and in hindsight, I probably shouldn't have used utilized a lot of them. A lot of people are going to give 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 watch this video, you've got to go out and find a mentor you gotta like grow a team. Like every every man and the dog is going to give you 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 hub and these things. So in the early days, if I was looking back on 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 a fast, smaller sort of opinion and really sort of like lent on, you know, a lot more books, a lot more audio books from people that are perhaps out of reach, because that's really where you kind of want to want a head to. But the biggest thing, I would say is just focus on your product, focus on your you know, your market, and do it. You know, and then a lot of these start up things in these places, they're going to tell you got to go get a t shirt with your brand on it. You know, you got to go kind of be like what you yeah, that's little TV show. I think it's what sillic in value or something. You know, you gotta go kind of play the the cliche. But yes, yeah, no, I think there's something to be said and I think a lot of people get wrapped up in the training and the edgy, which it is all important, but you're actually going to learn by executing and learning in the middle of it all as you are doing it. Well, how we're gonna love like humiliating yourself. That's it 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 of people aspire to do some career path similar to what you have been able to achieve. As you are, you know, leading the team over at Travalla, how are you creating a culture that is, you know, we're failure is encouraged for them to grow. Yeah, so what I would argue here is you really need to communicate the goals very clearly of where you're going and hold people accountable to their path on that goal. And our goal is very simple. It's always to make more money. Make more money, spend less money, you know, increase that that kind of gap there and being in sort of the marketing or I've even thrown that word away like I like to use the word growth, because that's effectively...

...what we're trying to do. We're trying 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 let you brag about, is what did you do this week that actually led to growth? I don't want to hear that you know, you had to do this operational task, this or that you I just want to hear what you have for growth. And you know, it's been quite effective because everyone has something to bring to that meeting now that we have there and we make everyone really well on the on my team, really well aware of the the situation that the business is in, what's going on. It's almost sort of brainstorming and we're coming up with ideas. They're relevant to our situation and I want to leverage them. I just want us to all work on the best idea that's going to get us to where we need to go. I don't mind and who it comes from, as long as we're doing it. And the other rule I have, as well as focus on growth, is when you're coming 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 to other people in other areas the business to do and they they but you know what, it comes time for them to drill down and actually, you know, jump in into the work, they're not so keen. So we really encourage that as well. And it can be something like I really want to do 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 to do 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 and it's going to be beneficial. So I'm not saying don't do anything that you haven't done before, just you know, kind of know what you are able to do get there, and then that makes my job quite fun because I start 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, and get them believing in themselves a little bit more as well too, and it really really does have a pretty powerful impact on our growth. Yeah, I can imagine. So a lot of a lot of the things that I here pretty often are is like how to make these meetings more efficient, and so I love how you are seeing keep it very simple. It's like, how have 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 your team on the back end of I have you been able to see this drive like a efficiencies within your medians, but also has your team been able to execute their roles? Yes, it certainly has. And then time amount efficiencies. I had a meeting to this week with with with one of the team and 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 this is 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 time and in future we catch up on these things. Say Hey, been last week, I did this, this, this, you know, like if if it's within your grasp, between your reach, get it done. So we'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 put something 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 not surgeons. When someone makes a mistake, you know, no one dies. You know, worst case scenario that's going to happen is you know and you know you might lose your job. That's like literally the worst thing that can happen. The realistically most worst thing that can happen is a website might go down. So the stakes really aren't that high. So if you're coming into stuff with good intentions and you know what you're doing, I really say go for it and then, you know, we'll chat about it if something's not quite right afterwards. But I'll never get angry at someone or be disappointed with someone for trying to grow the business. Yeah, that's easy, and I think the environment that you are creating there is probably extremely empowering and allows people to take ownership of different initiatives and of their roles as well, so they feel like they can actually execute and drive the growth for you without feeling they have to get approval on everything, which...

...ultimately could cause a lot of road blocks along the way. So previously we had talked about you said, you know, if you transition for that corporate world and you go into like this entrepreneurial ship phase, you have to roll up your sleeves. You're going to be wearing mini hats along that process. Along your journey, been able to develop quite a array of unique skills, and one of the things that we were going to talk about today are what we're some of the biggest mistakes that you have made in your early stages or things that you would have done differently as you look back. Oh, okay, yeah, yeah, into the good stuffs, into the good stuff, the good stuff my way. Where should we get started? I like this is feels like therapy to get some stuff off my chest. I think I'm the big let's let's look back on like when you were first hiring your first team. Let's talk about any mistakes or any advice you'd give to anyone out there who is about to embark on the journey. Yeah, yeah, first thing was is I was I was cheap. You know, you're watching the pennies in the early days, there's not much of a difference between like your money and a companies money. You know, 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 a lot of money by buying cheap people rather than getting experts. I wasted a lot 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. And the 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 were of a similar skill set to me that we as a business would be able to go together. But the second thing I assumed that everyone like thrive for success in life and that would everyone's sort of like thrive for success. was similar to what I had defined success out as well too, because you're having the the conversations of sure Evan's had. You know, give, give out a little bit of equity. This goes somewhere. You know this is going to be really cool and exciting and although you know you'll get that persona back in front of you, you know when they're going home or thereof they knock off for work. You know their headsets in a really sorry their head space on headset, their head spaces in a very different place to where I am when and sort of I'm never kind of turning off and really pushing. So that was it was a pretty, pretty big mistake there. Also in terms of hiring. You know, it's firing people that you've hired, that you've paid. That was toff. I should have fired a lot more people. I let of a lot of people that were not succeeding, struggle for a long time and it really brought down the business. The cultural problems that it created were catastrophic and take a very long time to correct. themselves. I mean 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 you budget, someone's got to go. So it's like, Hey, it's not me. You know, I like I can kind of give myself's not how I do it, but I kind of give myself that little monolog in my head here. It's like it's yeah, it's a hundred percent your decisions that you're getting into, but then, at the same time, by not making that decisions, letting people struggle and flounder, etc. You know, the business isn't growing, you're not moving for while, you're not moving forwards and you're ultimately shooting everything in the foot. So that's what it would come around to 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 when I when I interview people, are like to get to the crux of like what does success mean for them, and some other things you do as well to as you do have mental health problems. I, like everyone has mental health problems that come into to this and something that don't know. I meant that. So everyone has mental health problems in general. Not everyone who's in start ups of mental health problems. I mean they might. I don't mean darted to prove that. I won't get down that, but you know it. The startup communities, they do attract a lot of people who it is a friendship circle and it is kind of like a culture, well sometimes for some people who are a bit of...

...outsider. So you do pick up people that perhaps don't have the best support networks and stuff in their personal lives and they need to kind of lean and on that. And Yeah, that obviously has its has its own struggles. So I think I made almost every single mistake you possibly could make with with hiring people. The only thing I will 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 you will, but they were all sort of good people. Yeah, okay, fantastic. So you were hiring really nice people, but along the way your you would have shot a little bit. You would have invested a little bit more money into that, into the experts, rather than trying to develop from the bottom up. Absolutely, and, you know, we do still have some people with us who, you know, did come from, you know, the old way of doing things and they really sort of push themselves and they had a suppose, a closer definitions of what my success was to me, but they were, you know, they were the Unicorn, they were the the they were the exception to the rule. And again, I learned that the hard way. What would you say, as you're kind of building the brand for either your own companies that you started or for Travala, what were some of the mistakes that you'd meet along the ways you're kind of like building that Britain. Is there anything that comes to mind or that you have done differently? Yeah, hundred percent. Not Talking to people, not talking to your customers, trying to lean on things like ads or social media or email automation or any of those like hot topics rather than going out and literally knocking on some doors and having discussed with people about what they want, what they need and trying to sell stuff. That, ultimately, is always the mistake. I've developed a saying like from it is like I would rather sell to one person then I would to tend people. I'd rather sell to ten people than a hundred, a hundred to a thousand, because it's about the thousand mark that you really need to you can't be having one to one conversations or really get a proper feel for what's going on. But in those early days, 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 until you 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 really see some growth with that vertical was there a like a process that you put into place to make sure that you were kind of building that report with your with your customers, as you guys were continuing to grow, or is it just being more conscious along the way? It's been more conscious. I think you know there's people are also random, right, and what you're doing can be so random. So it's sometimes real tough to to be say you you have to do this, this, this, this, this, see a being conscious, I think, is a fantastic word, and sometimes you literally don't need. It's just common sense. Some stuff it's ultimately common sense and you don't need lots of data or lots of verification for it and it just works. But there are other times you need lots. Yeah, I would say never stop listening to your customers and always change your questions. Like I also notice people will start to tailor questions for certain answers that they get and they can miss details when they're they're talking to people as well. So be conscious of the the feedback you're getting, but also be conscious of the feedback you maybe looking for and be a little bit of reverent with yourself and if you 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've had so much well, you've put your heart out there, you put an idea out there and it's being beaten up so many times that you don't feel that anymore, because then you realize reach this kind of self actualization phase where you can just ask things and you're not going to take it personally when maybe people don't like it. Yeah, that's a big skill to that. A lot 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 you no longer are, it's probably because you've done it so many times that you're just you accept the feedback and you keep on marching along. Absolutely, and I look some people and naturally better at not caring what others think. I'm not one of them, so it took a long time to for me and that's it. Everyone's different as well. But yeah, again, I'd put this as like an example WID talking about before with the team. Is If that's the destination and that's the goal, you know reach this point that you don't take it personally and everyone's there, that's the North Star and that's what you 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 building and scaling Travalla and you're developing your team internally as well, as you look back, was there, was there anything that you would do differently as you kind of car about these careers or inspired people that came into your company to thrive? Oh Yeah, Oh yeah, and captain, hindsight is such an amazing thing. When I came into the business, it was sort of with as a merger. That's why I joined. I came from a company called travel by 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 a really sort of flat structure to having some more higher archy and and these things to it. We do have a large part of our team in Vietnam as well. I didn't really understand the culture of their work environment that they're in or how things had worked before. I really tried to push, you know, sort of like what I wanted, probably a little bit too hard without understanding the the circumstances in the situation that was there. So yeah, you know, and I kind of broke my promise. I sort of initially said to the guys when I came in, look, I'm not going to say much for the first month. I really want to observe things. But then I spat like day for I started to say things and kind of missed out on that opportunity to fully understand the business that I was stepping into and the way these these guys were working. Having said that, you know the there are some positives to it, you know, like conflict can be good and shaking the barrel and changing expectations and exchanging standards of things can be a good thing, and I'd love to say that, you know, I had fully planned out what they was going to look like and it was a fully calculated decision 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 created along the journey for me to help get them to where they need to be for the business to grow at the rate that we are right now. That that's really interesting that you'd mentioned that when you first came, when the murder it happened, you were going to lie yourself a couple months to really understand the cultures. From one month. One month. Okay, yeah, I was getting to my question. was going to say, what is it? What is the appropriate time? Would you say if somebody was an in your position? 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 going to be sort of aware of it. You might not have had the opportunity within a month to fully experience like enough Dev cycles or you know, there's all sorts of things that can happen for how that culture works. There's going to be layers of layers. You know, on boarding something or someone into a company 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 have a probation period and if you're really kind of sitting on your hands or kind of running at fifty percent, that's probably not a wise career decision. But Yeah, look, I would say a month, but be be conscious to maybe 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 culture in the environment that you are developing over a Tra rolla sounds like something very encouraging in empowering to be a part of.

If you had to recommend one book that the biggest impact on your professional development, what would be like that one book that you would recommend listeners read? Yes, sort of one of the books that help make me decide that it was time to quit the corporate world and and go down this new path. It's extreme ownership, one that comes up 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 where he will help businesses to lead effectively, to take leadership, and he puts up against scenarios, against time and war. So basically, so to be like, I met this CEO, he was having this problem, thought it was the end of the world and then the next bit'll be like a reminded me 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 and I just like the notion that, you know, you can take extreme ownership 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 for joining us today and sharing a lot of insight on a lot of the mistakes that you've made along your career path and embracing changes as you've gone from the corporate world into the startup environment and especially in the travel industry. If any of the listeners wanted to follow up with you, what would be the best way for them to reach out? Oh, twitter or being an encrypto and big on 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 of the sales engagement podcast. To help this get in front of more eyes and ears, please leave us a shining five star review. Join US at sales engagementcom for new episodes. Resources in the 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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