Website - Ep10 Dylan Cowan Creating Salesstar Podcast

Ep10. Dylan Cowan. Growing up in Sales

Join Pete Evans as he speaks to SalesStar’s youngest salesperson Dylan Cowan. Dylan has been at SalesStar for just over 12 months and has learnt a lot of the basics of selling.

At 19 year old Dylan has experience with speaking to CEOs and Managing Directors from multi-million pound companies. The pair talk about Dylan’s first steps into sales and looks at what he has learned in his last 12 months including sales mindset, the ability of coaching and the power of listening.


About our Guest

Dylan Cowan is at the beginning of his career with a true passion for sales. He is due to start a 3-year degree apprenticeship in B2B sales at Leeds Trinity University. Dylan has a strong desire to become recognized and build a large network in the sales industry.

He is strong leader and experienced captain with a keen interest in many sports. He has travelled to Japan and Singapore to represent his school playing rugby.

“I am eager to follow in my parents footsteps as a successful salesperson.”

About our Host

Pete Evans has over 20 years sales experience with a successful corporate sales career. If you’re involved in B2B selling, cold calling, sales recruitment, sales training, sales coaching, sales transformation or have a desire to grow your business then this podcast is for you.

Pete is currently MD and Practice Partner of SalesStar UK. SalesStar combines sales training with sales coaching to deliver long term results in line with your sales strategy so you can smash your targets and grow top line revenue. SalesStar works with growth minded CEOs and sales leaders who are frustrated with their sales results and are looking for a proven system to grow sales.

Episode Transcript

Oliver Eaton | Pete Evans | Dylan Cowan

Welcome to the Creating SalesStars Podcast. Each week, our host, Pete Evans, will be joined by some of the big and upcoming names within the sales industry. This is brought to you by SalesStar UK.


So good morning to everybody who’s listening to the Creating SalesStars podcast. This week is our guest is Dylan Cowan Dylan is the first sales apprentice for SalesStar globally. And Dylan has been with the SalesStar in the UK now for just over 12 months. So we’re delighted to be able to welcome Dylan to the podcast and get some of Dylan’s insight into the world of sales and sales challenges. This week, from a completely different perspective. So welcome, Dylan.

It’s a pleasure to be here finally on the podcast.

OK, so Dylan, you’ve been working in sales now for just over just over 12 months. Would you like to share with the listeners some of your own insights into the world of sales? And what’s the one thing that you’ve really picked up in the last 12 months?

Yeah, I think the one thing that I’ve really picked up is not this is in the sales side of things is actually you’ve got to listen. I think a lot of people, especially if they’re not been in a sales role before or they’re coming from school or college, it thinks sales is all about having sort of the gift of the gab being a real sort of extrovert, being confident, making sure you look really good and smart. But the one thing I learned in the early stages was how important it is to actually listen, and it’s not all about just being sort of a typical salesman that you might see on a piece of paper say.

OK, and well, obviously, you know, you are part of the sales team within SalesStar in the UK. And what sort of sales are global? What what sort of tips could a sales manager pick up from what you’ve learned in the last 12 months? You know, you’re obviously not in a managerial role, but what those are things that you picked up from your journey with SalesStar that sales manager could use when they’re working with their salespeople?

Yeah, I think one of the things they can definitely pick up is. That you can sort of can change anybody, so it doesn’t if they’ve got a certain characteristic, you can actually teach them or the characteristics, or you might get somebody as an introvert. You can actually teach them extroverted ways. And this can go down to things like how they prepare themselves. They get organised. And that wreaked confidence throughout that if you’re in the right mindset. So the main thing that I’m sort of circling around is you can actually flip somebody’s mindset from being one end of the scale to a complete other.

So it was interesting you mentioned about mindset, you know, before you sort of came into working with SalesStar how important did you think mindset might be in terms of your future or did you think it was all going to be about some skills training?

Yeah, I’ll be honest, I didn’t think mindset was important at all of the hear about things like mindset in elite sport and elite athletes. But you don’t think it comes into things like sales and when you’re working in a business environment. So I think early days we at SalesStar as a team in the UK really pushed on how important mindset was to succeed. And a lot of things actually can relate to sport in the sense. One of the former elite level, and you got some of the elite mindset and that goes across every single industry, whether it’s for whether it’s business. So yeah, it is the most important thing, I believe.

And how do you cope, personally, when you come up against somebody who’s perhaps not got a growth mindset, which might be, you know, in your circle of friends, family or whatever? How would you cope with that now?

I think I feel like I’ve massively improved my mindset and have people similar age to you who may be going down different pathways. And that might be the sort of where they think at the moment. But it’s kind of want to surround yourself in a similar circle to who to what you want to do.. Being only 19, you’re going to have a lot of different mindsets in your age category and your friendship groups. But it’s about. If they don’t appreciate that and what the journey that you are on, then. You know, that’s up to them, but you’ve got to be quite bold in the way you do things with the different videos that I’m doing and like I am here today, you won’t get a lot of people my age doing these things. So you do have to kind of stick your chest out and take a deep breath and go right. This is the way that I want to go.

Oh, well, yeah, and it’s interesting you mentioned about in the videos. How did you feel when you were first asked, you know, start recording some videos on your view of the sales world. How did you feel at that stage?

Yeah first, when the first idea is kind of flinging around, I was quite nervous for it and I wouldn’t be sort of jumping, jumping out my seat to go and do it. But we knew the bigger picture, the discussions that we had. So I kind of, like I said, just rolled up my sleeves and right, let’s just go and do it. And you know, you’ll see the difference in what a month, six weeks can do with, with the way that I’ve come on the actual videos. And actually, the mentality towards it now has completely changed. Now I really, you know, if me and Oliver find a topic that we can talk about or just something sparks the top of my head, all of it, I’ll get the camera out and we’ll get set up and then it’ll be out the next day. So yeah, I think we’ve had a big change from when it first came around, but I was definitely I was definitely quite nervous about the whole idea.

So when it was sort of first discussed with you, did you feel that stage, you might have had a sort of fixed mindset towards doing something a bit different?

Yeah, I think I did. I think at that stage, I probably like to say that I had I’m open to doing anything to improve myself, but I probably had a bit of a narrow mind towards doing putting myself out on social media, actually filming myself and talking from just from the top of my head. A lot of the time on what I know, and that’s all down to maybe a bit of confidence, maybe some barriers when it comes to people judging you also. Actually, I’ve realized since doing these videos, I know a lot more than I thought I did because a lot of the stuff that we do is off the cuff. Looking back at the videos, it’s like, oh, actually, I do. I do know a lot for my age, and maybe at the start I thought, well. Can I come across to other people and some of our target market where I know what I’m talking about, where is it? I probably had some limiting beliefs. And that was one of the big things where I thought, how can I come across? Well, actually, it wasn’t about that. But now I know that I can come across well and I’m confident in what’s up in my head, basically.

OK, you’ve talked about this, not the end of the fixed and the growth mindset. And obviously one of the things that you feel that you receive from the team at SalesStar is coaching. How important do you think coaching is to developing sales? Because this is something that ourselves as sales start talking to prospects items? How important do you see coaching in developing yourself and your skills?

Yeah, I see it is massive importance, but. The main thing that I’ve realised is I think a lot of young people, they want to learn and they want to be coached. It’s actually I think coaching is not just about you get the call, you get these qualifications and you just jump into something and you learn on the job or actually got people who are experienced and we see it in our own team who they really embrace the coaching, they embrace the learnings and they look you can see the performance change the way back to how important it is, and it is really important in the sense of. It had improve performance by doing so. And, you know, results is everything in sales, but you only get there by putting in hard work and putting in the hard yards.

And so I’m going to come back to some questions around coaching. And so share with the listeners today. Dylan, what’s the toughest coaching lesson you’ve received from anybody? It could be internal within SalesStar that could be external. I would like to share what’s the toughest thing that you’ve been coached and or learnt?

Yeah, I think. And when it first when the prospecting calls came around and all that side of things, especially jumping, doing the first sort of practice was really tough. I did it with Ian Bryan and he played a grumpy CEO, so that was definitely an eye opener. But I’m still way off the level that I want to be, and I can’t, because I’ve booked a few meetings and been involved in a couple of deals that we’ve got over the line as a team. It doesn’t mean that, I’m going to stop there. So it’s an ongoing process and I’m trying to improve every week and. That’s the reason why it’s tough is because I’ve been here a year, and I’m still not. Not by any means mustard. So it’s the it’s the ongoing improvements by doing things like daily role players, reading and listening to podcasts from sales experts to really improve the level that I want to be want to be at. And that’s why I found it the toughest because of that. Is not just a quick fix that you can do in a week is something that’s going to have to be implemented over a long period of time, and I don’t think until the day I retire. I don’t think I want to be stopped doing these things and to myself or somebody else coaching me on Prospect and cold calling. OK.

So it’s interesting. You mentioned about role players and obviously one of the things you’re tasked with doing is doing a role play every day. Yeah with different people in within SalesStar and all that you’ve done one with Oliver, you know, our digital marketing executive, how do you find that discipline and rigour of having to do those role players on a daily basis? It must be, you know, some people say that’s quite tough to do it, you know, practice on a daily basis.

Yeah, I think. The discipline side of things is making sure that I actually get things organised. The week, the week or two weeks before, because obviously time is precious and the people you want to practice with, they’re always busy. You can just book in them slots with them. That’s one side of things. And then once, once you’ve committed to it, then you’ve got to go out and prepare yourself. What? what do we want? What do we want to take on this? We’re going to go through and then the feedback that they give you, so. Actually, that’s sort of the confidence to go to Paul our CEO in New Zealand. Break up a little bit earlier and then the evening before us dead on. I stayed on a bit later with Leigh Parker, who’s also in New Zealand, kind of having that just go and do it because like I said before, you’re going to sales as a results game and you don’t get results by just kind of fluke and fluke in your way through. Yeah so actually, the discipline side of things is about the preparation that you do before. Going into it, being prepared when you’re on the call, he’s just. These things are just so valuable for a young salesperson, but I think my advice to anybody in sales, if you can reach out to someone who has already been there and done it or even someone you actually want to. Go in, you can improve yourself by isolating yourself. You actually take things when I do role plays for you. So it’s just good for all parties. It’s half an hour of your day. It’s nothing in the grand scheme of things, but the results that you can get from the. No, I’ve had a really good cause.

So what would you say to experience those people who say, oh, but role players are Unreal or not? They’re not worth doing because you have often heard the expression within SalesStar. So that, you know, we talked to prospects and clients that, well, it’s really expensive to pay your salespeople to practice on new prospects and customers. Well, what would you say to a sales leader or sales manager who doesn’t currently have a culture where the salespeople are role playing either weekly or daily?

I think you just hit the nail on the head. My question would be will how many cold calls where you think you’re doing really well on the call and then you just miss out on that meeting? You could probably somebody who makes 60 calls a day. You probably get at least one of them every day and you’ve got to think, well, if you did that practice the day before or did it in the morning, that one could change. That you could get that meeting and then you just got to put into numbers. If you do, if you think that happens every day and you can make that happen, not every day six five extra meetings a week, 20 extra meetings a month. And then you just put it into the numbers. So if you’ve got that caught your way, you don’t think it helps you. Just look at how many times that you’ve just slipped to the final hurdle or you’ve really wasted an opportunity with a prospect and you can close that gap there.

Ok? and you know, you’ll have seen others of us in the business practicing for presentations and preparing for those presentations. What encouragement does that give you when you see others in the business having to practice and role play and prepare properly for meetings?

Yeah, it makes you want to definitely get money before you jump onto a presentation or a discovery meeting. And likewise with Tim, Allison and Denis, if I see that you’re practicing and you’ve been in the sales game for how many years now…

too many years to remember…

…that if I see you practicing and I’ve only been just over a year, it’s kind of like, well, actually, I need to step up my game. And it just rubs off. I think if you’ve got that culture where your leaders and team are doing it and they’ve already had successes in the business, whether it’s in the past week, month years, they’re still doing these, these things that they’re in their rooms. That’s that kind of makes me want to go, well, actually, I want to practice what I’m doing. So, yeah, it does rub off.

Ok? How do you feel when you hear people say, oh, I’m just not going to practice, it’s not. It’s not worth practicing. How does that make you feel? Because you are, you know, you have your own coaching calls where you’ve heard salespeople say it’s not worth it’s not worth practicing role players are worthless. How does that make you feel when you hear other, maybe more experienced salespeople say that.

Yeah, just going back to that growth mindset, I don’t think they have that growth mindset and eventually it will catch up on you. We had a presentation from Jamie Peacock a few months ago, and he said he had to adapt his game every couple of years or even every year because. The 2021 version of me is not going to do well in 2022. If these people are not practicing and really honing in on them skills and giving it a different shift on what they’re doing. Version of the old version of them is not going to be successful, so. Not you might get away with it for two years, but when that third, fourth year hits, you’re going to start to. Behind in the park and everything changes in, but really quickly and in business, you’ve got to keep on the top of your game all the time if you want to be successful long term.

OK, that’s great, Dylan. So, you know, we know that you’re secure meetings with some CEOs and some MDs, and some of those have led to us as a team winning business. How have you overcome the challenge of being young when you managed to secure meetings, we see what can you share with our listeners that, you know, has really helped you secure some meetings with some quite big companies?

Yeah, I think the first thing is you’ve got to kind of change the mindset of you, just a young lad or a young lady where you can’t just kind of feel sorry for yourself and make excuses that younger. If you want to reap the rewards of sales, you’ve got to act like a big player. So that’s the first step. But also sometimes I’ll book a discovery meeting with somebody who’s the CEO of a large business, and then we’ll jump on the Zoom meeting and then they’ll see somebody who’s got a baby face and who looks really young. And I introduce myself and I’m 19, and that’s I think that’s worked in a positive way for us because. They’re seeing if they get in on a meeting with a 19-year-old or 18-year-old. I was for a bit of whilst I was here. And that’s going to make them think, well, what are their salespeople doing if, if, if, if, if he can do this? So I think a lot of the time I actually get a lot of respect when they see my face and I’ve done something credible and I’ve had a lot of praise since doing the videos. And a lot of people, when they do see me on the Zoom calls, they are worthy of being so young and giving me all the support. So I actually think there’s not as many challenges as I expect it to be in the first place. But as long as you block out that mindset of are you are a young person, you can get away with more. Actually, just get out of your head because you want to. If you want to reap the rewards, you’re going to have to step up.

One of the things we were talking about in the office yesterday was the fact that some organisations don’t want to bring in young talent in sales. It’s easy. Or let’s go and find somebody who’s gone in sector experience. They’ll know how to sell. What advice would you you like to share with the listeners? You know, people are thinking of hiring younger sales talent or somebody with no experience. What advice would you give to those people who perhaps have a bit of a fixed mindset about who they should hire?

Yeah, I think my advice is if that person has got the right mindset to learn and to really improve their skills. And than you will if you’ve got the right coach around them, you will reap the rewards of it like me and Oliver, a marketing executive. We’re both young people. And I think at the moment where we’re seeing the rewards of the risks that you’ve taken and I can understand you’re not going to hire a young person with no experience in the sales manager sales director Role. But if you’ve got an opportunity there for a young person who can really develop them skills. You you could just go and find a gem that that’s there, and there’s so much, there’s so much knowledge, and there’s so much talent in these colleges and schools that people don’t want to take that typical University pathway or some people might do trades, but they are. They have got a lot of talent there that don’t want to go down a typical University route. So but they can’t get into these top uni, if you know what I mean. So you get people who they get into the sort of Newcastle’s and Manchester’s the Durham’s, but they actually don’t want to go to the University. These people are all knocking around somewhere. And if you can go and find that person who’s got the right talent and the right mindset to grow and improve their skills. Then I just take the risk and you will see the rewards of it with the right coaching around them, you know?

So you know, you’ve been hired into an SDR or sales development role, which is probably what some would say that it’s one of the toughest roles in the organisation because you’ve been asked to make. So many calls and calls in a day. What’s your perception there? You know the role that you’ve been asked to perform with a number of calls and all the prospecting activity that’s expected?

Yeah, I think it is tough, but I think as long as we’ve got the right team around you. And you’ve got that mindset of actually want to improve yourself because it’s all good having a good team and helping you as much as you can. You don’t really want it as much as you say, do. And it’s going to be it’s not the thing for you, but I found that the shift from sort of going from University and school into college. And school, sorry into sales role. You do have a bit more responsibility. And that’s one of the things that we have been working on. Well, once you’ve got that organisation sorted, you’ve got the preparation sorted, your minds in the right space. You’ve got that real space to go and the targets go and develop your skills, go and really feel like you’re part of a team. And actually, you know, we’ve got things in place to me that the incentives and targets that I can hit and if you’ve got that legwork that you can go and achieve that. You’re going to feel so good about.

OK so where do you see yourself progressing then? Obviously, your trainee, you’re doing your degree at Trinity University. What was the future for Dylan?

Well, who knows? I think my eyes are still on SalesStar. And at the moment we’re doing the whole cold call and prospecting side of things, real front and stuff, thinking the next year, we’re going to try and develop my skills into the discovery phase and really learning all that side of things. And then, you know, the more I’m here, the further I’ll get in the sales side, the more involved our we’ve got our plans in the business internally, and I think when I can establish myself as a leader, the opportunities are really endless.

OK, so Dylan, what’s your final tip for our listeners today?

Then my final tip, and I think it’s been quite a big part of the podcast, is that as a young person, mindset is really important. And the most important thing. Coming out of school and college, you kind of get everything still a bit spoon Fed to you. And you don’t have much responsibility. You can an extent you can kind of go through the phases. You can’t really do that in a workplace. And if you do want to be successful, you’ve got to get your head in the right space and got to really have that desire to want to improve yourself and improve and put the hard yards in early doors. Because if you do put the hard yards in other doors and you’ve got your head in the right space, the opportunities are endless. You don’t really get lucky. You don’t. You can’t get lucky in sales and in a business environment. So yourself in the right mindset for when you do want, whether it’s after University or after college and get yourself in the right mindset to succeed and learn.

So what you’re saying, then, is there is no magic wand to access them.

No, I think there’ll be some weeks where I feel like I’ve made, I’ve made a sale, I’ve booked a meeting and I feel like on top of the world. But 10 days later, that can come crashing down and you buckle under pressure. So I think it’s about can’t just expect things to fall on a plate for you, and it becomes pretty evident within your own team and in actually yourself. You feel it that you can’t just sort of get lucky and wave a magic wand and your book. A lot of meetings get a lot of sales.

Yeah one final question, though obviously you’re getting coached on a regular basis by me, by Ali, by everyone in the sales team, by people globally. How would you feel about some of the tougher feedback you might have had?

Yes, I feel like I’m quite thick skinned anyway, but I feel like the person I am when I do take feedback. Adam, I’m not somebody who holds grudges. If if I get a bit of a don’t. Nobody shouts at me in the business. But if somebody says you need to open your game a little bit and not somebody who’s going to hold that on anybody or starts talking about it, for me, I actually see it as a positive. And go right if I’m not at the level that they want me to be. I need to go and really change things. And I think we all see as a team when I do get some feedback, I act on it pretty quickly. And you can see results pretty much almost instantly. So you do have to be quite thick skinned sometimes. And even as leaders, I think you’re really good at it. You find what’s right for people and how much feedback to give that person or how hard to go on them. But if you can find that level of how, how much you’re going to get back out of that person, yeah, then you’re going to yeah, you just go and back to the question if you’re the way you receive feedback is you just got to take it on the chin and then just go again.

OK and finally, Dylan, working people reach out and contact you.

Yeah, LinkedIn is the place that I like to sort of float around Dylan Cowan type in sales start at the end. If there’s loads of different colours in the world, I’ll just sell side you care page. You’ll see my face floating around on there all the time.

OK, thank you very much, Dylan. It’s been a pleasure to interview today and we hope to welcome you back in the future.

Thanks, Pete. It’s been great.

Thank you.


Thanks for listening. This podcast was brought to you by SalesStar and hosted by Pete Evans. For more information about what we can offer you head to our website at You can also find us on all social media platforms just by searching for SalesStar UK.


Presenter and Producer: Pete Evans
Special Guest: Dylan Cowan
Producer and Intro/Outro Voiceover: Oliver Eaton
Podcast Editor: Alex Mullen

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