Revenue Career Ladder

From Cashier at Wickes to Brand Growth Manager with Tom Boston

110 mins

In the opening episode of Season 2 of Revenue Career Ladder, host Jamie Pagan is joined by Tom Boston for a candid and often hilarious deep dive into the unorthodox career path that took him from a DIY store cashier to a standout brand voice in B2B SaaS.

Tom shares how moments of feeling lost, accidental detours, and pivotal support from others shaped his eventual discovery of a unique professional lane—one that blends creativity, comedy, coaching, and content. This episode is a heartfelt conversation about figuring it out late, staying true to your voice, and building a career by embracing what makes you different.

Expect to learn:

  • How retail and acting prepared Tom for a career in B2B sales
  • Why “being yourself” is a strategic advantage in sales and branding
  • The unlikely moment that kickstarted Tom’s content career
  • What it’s really like building a personal brand from scratch on LinkedIn
  • How content, coaching, and career alignment came together at MySalesCoach
  • The importance of mentorship, honesty, and figuring out your strengths
  • Why it's okay—and even helpful—to feel lost early in your career

Ready to take the next step in your career journey? Subscribe to the Revenue Career Ladder today and start making your professional aspirations a reality.

Unlock the power of data for both Marketing and Sales. With Dealfront, you can not only target the right prospects and run smarter campaigns but also empower your sales team to close deals faster by aligning them with high-intent accounts. Drive sustainable revenue growth and maximize ROI across both sides of the funnel with one seamless solution.

Follow Tom Boston: LinkedIn: https://www.linkedin.com/in/tom-boston/

Follow Jamie Pagan: LinkedIn: https://www.linkedin.com/in/jamiepagan/

Connect with us: LinkedIn: https://www.linkedin.com/company/dealfront/ Facebook: https://www.facebook.com/getdealfront/ Instagram: https://www.instagram.com/getdealfront/ TikTok: https://www.tiktok.com/@dealfront X: https://x.com/getdealfront YouTube: https://www.youtube.com/@dealfront

  • Jamie Pagan

    Jamie Pagan

    Director of Brand & Content at Dealfront

00:03 Welcome to another season. So season two, which we are recording the same week that season one has just gone live, which is wild. So we're on season two already. And who better to join us than Tom Boston to talk through his career journey to give hopefully some insights, actionable tips, and maybe even a little reassurance that the journey is yours to define. We're to be chatting about his journey from cashier at a DIY store.

00:31 to brand growth manager. But before we jump into that, how are we Tom? I'm very well, Jamie. Yeah. Great to great to chat with you. And thanks for having me as your first conversation of the new series. That's exciting. Yeah. Do know what? We've got already got 10 names set for season two. And I was like, right, who, who do I want a season to kick off episode one? And it was yourself. So

00:56 We've spoken before during my time at Selligence whilst you were at SalesLoft and we kind of spoke, we did touch on some of this career background, but this is going to be 60 to 90 minutes of fully the whole career, the ups and the downs. We really should have called this revenue career snakes and ladders, not just ladder, because what we've realized is that the career journeys are not linear. They're not logical in all cases, but

01:25 We always start with your first ever job. So talk to me about your first ever job. And I mean, your first ever job that might not have been legal. It might not have been paid. What was the first one? Well, it was legal. I want to get that for the record. Yeah. So my first ever job was as a cashier, right? For a DIY store in Leeds, I was a fresh faced.

01:55 16, 17 year olds, how old are you when you're six form? was at sixth form at my high school and I just needed a job, right? Like everyone in the common room seemed to have a job and have some money. I thought it'd be probably good if I had like one of those so I could go to the pub, right? I mean, does anyone else get a job for any other reason? You know, that was my...

02:24 kind of my mindset. need to be able to hang out with everybody else. So yeah, someone, someone in the common room said, I work in a DIY store. Do want me to get you a job? I'm, I'm quite lazy. So I went, okay. Um, yes. And I was there for quite a while. Right. And it was, it was somewhere that was close to my house, easy to do. And I was there all throughout.

02:54 sixth form and then even into university. So yeah, I was there. I was in the DIY store for a good, a good stint of my early career. And in the for those listening in the UK, there are probably three colors that people attribute or sort of relate to DIYs. You've got orange, green and blue, which which were you? I was blue. I was Wix.

03:23 you know, that was the DIY store of choice. Again, I'm not a big DIYer. I'm still not really into DIY, but as you'll know about me, Jamie, I do have a keen interest in acting. And whilst I was working in a DIY store, I was also studying drama.

03:51 And I very much used that in that role, right? So I would basically act like I knew what I was talking about. So the builders would come in and they'd say to me, know, I'm 16 years old, 17 years old. The builders would come in and say to me, know, when you're, you know, when you're putting up a fence and I, and I'd sort of go, I just mimic them. Oh yeah. Yeah. Yeah. Yeah. Yeah. Go on.

04:19 They'd like, what kind of, what kind of cement should I use for the posts? And then I would just go, well, you could try, you could give this a try, you know, and I would just kind of like pretend I knew. And then, and then they would go, yeah, cheers, cheers mate. No problem. So I spent a long time in that role, just kind of acting like I was one of the working class, you know, salt of the earth, actual workers.

04:48 who would come in and would, you know, do it in real work, I would pretend I was one of them, so that they would like respect me and not see me as who the hell is this guy, you know? And to this day, do you know what the correct cement is? No way. No, I honestly, I learned very little. The answer for everything and anyone who works in retail is always you could give it a go, you know, give it, you could try, you could.

05:17 And often if you answer confidently, and I've definitely taken this into sales, if you answer confidently, you sound like you know what you're talking about anyway. Right. Now, this theme has come up quite a lot in previous conversations we've already had, but retail and the face to face sales in early years tends to help massively with sales career further down the line. I would certainly agree with that. You know, it's hard making cold calls.

05:46 And it's difficult facing rejection, but when you've got a customer who is right there, who's maybe upset, maybe some idiot has sold in the wrong cement the week before, you really do have to think on your toes. Yeah, do know what? The local B &Q was getting the guys that you were giving advice to in Wicks, following week they were like, you never guess what, I was in Wicks last week and he fucking told me to use this cement. The guy didn't know, he was clearly making it up. thought...

06:16 He thought he was pretending to be one of us, but he really wasn't. And how long you said there was a good stint until sort of like your early 20s. How long are we talking? Far too long. We are talking five, six years. And I was there throughout my time studying A levels. And then I found myself going to university to do a drama degree.

06:46 on the first day they said you will not be able to hold down a job whilst at university you are going to be here every day weekends late nights rehearsing writing so I just quit right I just listened to what they said and thought oh I probably need to quit that part-time job so I quit my job and then I

07:16 I was about three months into university and I realized we're just hanging around here, right? We're spending a lot of time going to coffee shops and Nando's. There was no late evenings. Everyone just wanted to, you know, same thing, go to the pub. We weren't there on a weekend. So I found myself going, I wonder if I should give them a ring.

07:46 Then weirdly, I saw my old manager in Morrison's of all places and he said, how's university going? And I was like, it's good. I've got a lot of free time in my hands. And it was him who said, you wanna come back? Do you wanna come back to Wix? And I was like, again, so lost at this point, no idea about like.

08:15 what a career that looks like. I just said, yeah, let's, let's do that. So I got my, my part-time job back and then I was there for three years. And then even as I left university, I was still, I was still there. So yeah, a good old, a good old time. At one point they called me a lifer. They said, Tom, you will be here for life, which terrified me to my core. know? Yeah. Do you know, I work in,

08:44 I live in South Wales and South Wales is probably like some areas of the north and it's very, very common to have lifers. I worked at the Royal Mint, so the company that mints coinage for United Kingdom. And there was a museum on site and there was a guy who had been there for 50 plus years. And that that really I was like, my imagine coming to the same place for 52 years or something like that.

09:13 So you were, when you were in university, you did drama. Did you get to the end of your degree? For me, I got to the end of it. I was like, do you know what? I actually don't want a career in the thing I did a degree in. That's completely fair. I certainly didn't want to go to auditions and, you know, try to be an actor. The joke was that everything I did at university,

09:44 I just played myself, right? So if we were, if we were doing Shakespeare, it was, it was Tom Boston as, as, right? Same accent, same expressions. So was like, well, I can't really be an actor because all I can do is, is this, this is all I've kind of got. Did a, did a few kind of extra roles. thought, maybe that could be something that's quite interesting. So got an agent.

10:14 and did some work on some TV shows. But again, hated every second of it and felt like, demotivated, demoralized. Anyone who's ever been an extra will understand what I'm saying here, but you're called an essay. So you're a supporting actor. And the essay on set is the least important.

10:43 person. There is no one less important than an SA. And I remember we were on set once for a show called DCI Banks on ITV. And I'm an awkward guy, right? If you meet me, anyone who's worked with me, I'm six foot one. I'm too tall for myself. I, you know, I'm not very confident. I kind of struggled being an extra because I'm just...

11:11 I just felt like out of place. A good extra should look in place, right? Not out of place. And I remember being stood in the way and I felt like I was in the way and I heard the director say, can someone move that essay right now? And I remember just feeling like, I don't wanna do, this is not for me. It's very exciting.

11:41 that it's ITV and there's cameras here. But I think I've, you know, I think I've got more to me than being spoken to like I'm not in the in the room. So I kind of gave up on that. Right. So was like, OK, well, I can't I can't be a proper actor. And I don't really like being an extra. And which kind of got me to shut the lid, really, on the the acting side of things. And off the back of

12:10 university after doing those bits and pieces here I am still in the DIY store. It's a bit lost, you know, to say the least. Yeah. You, you mentioned that you, you've only played yourself like Tom Boston as Macbeth or whatever, there are many, many a career actor who've seemed to play the same like Tom Cruise, right? He's played basically the same character as entire career. Uh, very

12:38 cold, miserable action hero or action guy. That's basically him. So there could have been a career in it. So you graduated how many years after graduation was it that you were Wix? Yeah, I think it was like a year and a half or two years. It's when I met my now wife who just instantly questioned, why do you work there? She came in asking for some evidence for offence.

13:08 Yeah, she had a shelf to put up and I was right place right time and She was like, do you work there? And I said, I don't know and then I pretty much I think it was six months after meeting her I'd handed in my notice Because she just kind of Got me to reflect really on okay. So that's interesting because again, we've spoken about this before maybe a couple of years ago But so it was your wife that was almost like the catalyst to what's next

13:38 Yeah, I mean, I wasn't just lost. Career wise, I was pretty much lost in general, right? Just like 20, 25, 26 friends had got real jobs with partners. And I was kind of like hanging out with them whilst they built their real lives. And I was just, you know, mid 20s doing nothing.

14:07 And it was, was kind of scary really. Um, and then you kind of panic, right? You think, Oh, maybe I shouldn't have gone to university. Like a lot of my friends, um, they got apprenticeships, 16, 17, seven years later, they're in senior positions. I'm still a cashier. Uh, you know, like red flag. I've made, I've made a terrible decision. Um, so yeah, it was, it was her that got me to kind of question. Yeah.

14:36 What are you even kind of, what are you doing? What do you want to do? And there's more to life than being a cashier. So I was very grateful to her for that. Do you know what I think is quite nice is that the way in which you've described you felt at that point of being slightly lost and that your people within your circle, your friends.

15:02 even peers seem to have had something figured out and they were progressing. I think that's how a lot of people in 22, 23, 24, that sort of early to mid 20s kind of feel because you either tend to go straight into something when you graduate to 21, you go straight into a grad scheme or an apprenticeship or a career that you've done your degree for, or you're kind of just thrown back out into the world of trying to figure it out and there's no rule book of like,

15:31 guide, there's no Ikea manual of this is how you figure out what you want to do. So you're kind of just floating around. And I think that's it's quite interesting here. You describe it like that, because I think you go, you definitely go through phases that through life. Like I'm, I'm 30 plus now and career wise, great. But I do sometimes feel a bit lost in that I'm single and I've got all of my mates are pregnant with dogs and family. And then I'm like, I'm like, Hmm, like you said, red flag. I'm like, right. What do I need to do here? So yeah, it's very interesting.

16:02 Yeah, it can be difficult, right? We spend our whole lives comparing ourselves to other people. We can't help it. Especially people who are of similar age, but the comfortable reassuring thing is that there is no, like you talked about, there is no set path. And everything that I've done up until now has led me to this point.

16:31 And I'm grateful for that, you know? And I have learned something in every role that I've done. There are hints of the managers that I had in the DIY store in the character that I do now. they definitely are. And I'm grateful for that, you know? So speaking of those things that you've learned,

17:01 It's a nice segue into the next step. And so you were after about six months of being your partner, you sort of made the decision to leave. So what, how did you decide on your next step? If you, if you hadn't yet figured out what you wanted to do, what, how did you decide on the next step? Yeah. So, like you say, I was a, I was a couple of years out of university and I was playing around with like podcasting.

17:29 with a friend. Now bear in mind, this is like 2013. I was gonna say this is early wave. This is before it was cool. Are you saying that you are basically the person who led the wave? I guess that's kind of, you know, your words not mine. So we were like messing around with this idea of doing some sort of podcast.

17:58 and it was terrible. We were inspired by Ricky Gervais sort of podcast. He was very much at the forefront of it and we were like, oh okay, maybe we could mess around in a coffee shop and do a bit of podcasting. So like, I really enjoyed recording those kind of shows and I was like, I feel like there's something there.

18:28 So I'd seen that there was a job at my local radio station in Leeds to be on their sort of PR team. It was only part-time work, but I was like, you know what, as this, a quote from the office, it's better to be on the bottom rung of a ladder that you want to climb than halfway up one that you don't.

18:58 I do love that quote. That's good. I've not heard that before, but that is very apt for this series as well. Yeah, you can have that one. I think it was Tim said that one on the UK office, so I won't take credit for that one. So, yeah, I almost like you said jumped ship and I was like, maybe I'll join this PR team. mean, I say PR, it was literally put on a T-shirt.

19:27 with the radio station name and go and do like crazy things, know, go and do events. One day you're handing out flyers. The next day you're live on the radio interviewing someone for an event, like whatever it could be. But I was like, it'd be quite good to maybe be in that space because I do have an interest in in podcasting. So yeah, that was the job that I got in Leeds. And then it was my wife who got a grad scheme job.

19:57 in Newcastle. I'd never been to Newcastle. I was very much, lot of people will relate to this if they're from Yorkshire. Yorkshire is the best place in the world. It took me leaving Yorkshire to realise how ridiculous that is. And I'm so grateful to my wife for taking me out of that bubble and realising that there is more to the world than there.

20:26 than Yorkshire. So yeah, she said, let's move to Newcastle. I've got this grad scheme and there was a radio station in Newcastle that was twinned with the radio station in Leeds and they just transferred me and I was doing the same job up in the Northeast. So it was a really exciting time really to be in a new city with, you know, with my partner in this new

20:55 role doing these kind of these ad hoc stints with them with their PR team whilst getting to meet some of the presenters and sitting in on radio shows that were being recorded I was like this feels more like like me this is this is something I could get excited about for the first time you know and did you say that was that was unpaid

21:25 This was paid work. this was a I can't stress. It was ad hoc, right? So some weeks they didn't they didn't call me, which was not a real job, is it? If you don't work for a week, you know, two weeks. And then other times I'd be like, OK, so now I'm doing like five or six shifts with these guys in a week. This feels more like more like a job. But it was a sporadic which was difficult.

21:55 Did you supplement that with something else then to obviously keep money coming in or? I didn't, which is why I didn't end up doing it for very long, you know. There's only so long you can survive if you're doing this kind of ad hoc work. And it kind of dried up as well, which didn't help. You know, with those types of roles, you go through stints and then

22:24 Maybe they stopped calling you. If they don't call you for like I say two, three weeks, you're kind of like, I need to be, I need to be doing some, something else. Um, so yeah, it was fun and it was exciting. Learn a lot, got to do some cool things. Um, but it wasn't, it just wasn't something I could do long, long term. Now let's not forget. This is back in the day when I thought.

22:52 Career was gonna fall into my lap right very kind of naively if I'm Through the door of a radio station

23:03 they'll give me a show. That was what I genuinely thought, right? I'll just make friends with people. you know, whilst doing that role, I was like writing a blog about what it's like to work in a radio station. And I was like doing videos on YouTube about it, you know, all this kind of creative stuff, which I thought would lead to success. But no.

23:32 ultimately, you know, that's not how life works. People don't give you everything you want. You have to you have to work for it, Which I, which I learned. then because you said you learned, learned a lot. And I think based on what you do now and where people will recognize you from, it's clear that you took a lot from that. But what was the in hindsight and retrospect looking back, what was it that even in that short stint you took, you've carried forward? were the key bits for you? Yeah, I mean,

24:02 It was, it was fascinating to, to, learn about how they produce features on, on live radio. And I don't think they get enough credit really for that. Right. So if we talk about like content creation, think about like LinkedIn, Oh, I've got to create content. I've got to put a post out. I've got to create a video. Imagine being live every day for three hours.

24:32 and having a block for 10 minutes, five times a day that says feature, feature, feature. And this is just you thinking of something that's based on a phone in or some of the news that's trending at the moment. Basically just creating content out of nothing. And it's all audio, right? Cause it's just radio. So.

25:00 definitely alert a lot from that, know, how the presenters at the time were able to just create content consistently and do that and do that every day. And for the for a lot of them, it would just look like literally doom scrolling on the news, finding out what's going on at the moment. I would I would grab a paper on the way in and I would like circle, you know, ideas.

25:30 what I think would make a you know, good content for radio shows. So yeah, that was a big takeaway for me. Now, given that it was a short stint, you said it wasn't necessarily sustainable. What was the next, I guess, sensible choice to get more consistent income? What was the next bit? So, yeah, I got a job in retail.

25:59 I kind of like gave in if you like. I'd been doing these stints for the radio station. I was even doing community radio. But again, unpaid doing a show. And then my next kind of step was to go right well, I need to get a job that's actually gonna

26:28 going to pay me every month and for me that was Apple. I couldn't bring myself to get another job for a retail store that I had no interest in and Apple seemed like okay well at least at the very least I could maybe use some of my passion for

26:57 technology in that, in that role in retail, rather than having to pretend I like fences, you know? Yeah, you know, I, when I was at university in Cardiff, there's an Apple store there and I did, I've always had this, I liked the t-shirts and I've always loved Apple products. And I was like, I should have applied for a job in an Apple store. So you were, they call it specialist, don't they? Specialist at an Apple store. Yeah, that was it. that was center of Newcastle.

27:27 blue t-shirt you were a specialist there was no targets when it came to how much you sold no commission you you were just you just paid a standard retail salary but I enjoyed the role because it was all based on your MPS score so how happy was

27:58 customer when they filled out a form that they got emailed after they visited now making people happy Jamie is like one of my favorite things in the in the world and I was like this is great because I just make make these people laugh while they buy an iPad and then my manager says Tom you are great you are doing so well here

28:26 you know, people love you. I was like, well, happy days, because that was a good thing for me, you know, to be able to just ask people questions about their life, you know, sort of again, we're touching into like what I've learned for my B2B career, but discovery, right? Just like being curious, speaking to people about like what they are buying their products for. I loved all that. And, and yeah, I was also able to like,

28:56 do some things that I wasn't really expecting to do in a retail store. So they would get me to train often OAPs on how to use Apple products. So in Apple stores, I don't even know if they'd still do this now, you can sign up to, you know, an iPad lesson.

29:21 Yeah, they do know that I know they still do it. So I saw a video online earlier this week of an Apple store in America where a guy was hosting a garage band. I think their music app is Gordon. He was hosting a garage band workshop and no one turned up. So this girlfriend's boyfriend felt sorry for him and did the garage band workshop and he was the only one doing it. And there was like a mini auditorium of like 40 seats and it was just him playing with garage band with this guy because he felt sorry for him. So they do still do the workshops.

29:51 So those are the ones right and again I really enjoyed that right they would they would put a microphone on me which I liked right and I would be presenting I would train the elderly how to use their iPad they would often take multiple pictures on their iPad whilst I was training them and because I was stood up they tended to be of my belly

30:21 So that I would have like 15 pensioners with 60 photos of my blue belly. So somewhere on the cloud there are loads of your belly. As they as they left, you know, because we would do like iPad basics. But again, love that. Right. I was like, OK, this this feels like more than just putting items in a bag or scanning.

30:51 your products. It felt like a step up, even though looking back it probably wasn't a huge step up, certainly wasn't a huge step up salary wise and my wife will confirm that, but it felt like at least I was doing a few things in there that complemented my personality. So we would do like in the morning for example, apple.

31:19 stores you do like a team meeting and those meetings were all about energy and bringing the fun so they would just literally say to me Tom could you do something fun and one of the stories they always tell is I did something called chairobics so I got I got everyone on the apple stools and I I put the music on which was

31:49 Groove is in the heart and I put a sweatband on and I just got 50 people to be doing these chair aerobics to Groove is in the heart, which again, it was just like.

32:09 This feels more me. This is creative. This is fun. It's energetic. You should bring that back for those that work at home. Well, it's funny because I think I did a piece of content back in the back in the archives somewhere, maybe 2020. I think I stole that idea and did something along those lines, but I'd have to I'd have to dig out. This is when I was still experimenting with content. Yeah. So this is it's really, really interesting. So I love that I didn't realize that.

32:38 Well, back then, at least the Apple prioritized NPS customer happiness over. I mean, I guess for them it's because one, they make a shit ton of money anyway. They know they're going to sell people come to them without them having to do that much marketing really. And it's not really a hard sell to convince someone to buy an iPhone. But I think that's really, really interesting. Would you say that because you had this really nice feedback loop of you are good at making people laugh and making people happy.

33:08 you're doing a good job, would you say that that was a really big like confidence booster of being yourself led to good results? 100%. You know, I've always liked compliments and being, I'm being told I'm good. mean, why else would you build a personal brand on LinkedIn? Right. I've always liked people saying good job, Tom. I don't know why the poly cause I'm not a very confident person. Um, but yeah, to be able to, um,

33:37 to receive that kind of feedback and see the MPS reviews, right? You would literally get a review often that they would share with the group. And I was like, this is great. This is, you know, I'm just fantastic. So yeah, it definitely helped. And yeah, I had an interest in the products. I'm still an Apple fan boy, right? Yeah, same for me. I can't help myself. It's

34:06 I've got the phone here, I'm on the MacBook Pro. It's just been a part of how I work for years now. But yeah, it felt like the balance of I'm good at it, I get good feedback, and I like the product. Which is, again, that's almost like the perfect combination, right?

34:29 Yeah, what's there's that I can't remember what the Japanese name it might be caused like Ikigage or Ikigaki or something but it's I've absolutely butchered the word there but I might do ask the audience Japanese methodology for balanced life. It's called Ikigai. Okay, I wasn't far off. It's basically

34:58 Yeah, it's the convergence of passion, vocation, mission and profession. So do something you're passionate about. Or if you do something you're passionate about, you have a core mission. You have a profession that links to your passion. Like if they all meet in the middle, it's a balanced life. And it sounds like what you've just described there was it was something that you were at least mildly passionate about the technology stuff. It's something that

35:25 uh, helped build confidence and you could make money out of doing that. So that's the vocation side of the balance. Um, and it kind of gave you, you felt like you had a bit of purpose, which is an icky guy, balanced, uh, balanced life. Um, how long did you do that for then? Yeah, I was there for a couple of years. Um, at Apple. Yeah, I did, I did that for, uh, you know, it was at least eight, 18 months to two years. So it was a, it was a fair, a fair whack. And it sounds.

35:54 all really, really positive. So I'm assuming you left because was it that you were ready for something bigger or was there not progression available? They certainly didn't feel like there was an obvious next step when I was there. Right. Do you want to be a manager like a retail manager dealing with rotas? And I thought, well, that doesn't sound like

36:23 That doesn't sound fun. And then, yeah, we decided to get married, which was which was exciting, but so expensive, you know, like ridiculously expensive. If you put the word wedding in front of anything, you know, it becomes you want a cake, you want a wedding cake. OK, that's different, you know. And yeah, we we were pretty keen on getting married.

36:53 but we just couldn't afford it. I got my first job in B2B sales off the back of the Apple roll, which was for a utility broker in Newcastle. And it was a lot more money.

37:21 but it was a ice bucket of water over the face as to, know, having fun in the Apple store to cold call the 100 businesses every day to try to get them to switch there. Yeah, and utilities like cold calling is bad enough, but no one wants to call about utilities. I don't think there's anything harder to sell. You know, I'm cold calling you about gas and electricity.

37:50 It was like some hard sell, know, but yeah, difficult, you know, got upset often left with a headache. You know, I used to kind of leave with a headache and I was like, this is not something's not right there. It's not right. I be going home with with a a migraine. But Jamie, they were walking people out the door. For not hitting their target, you know, there was.

38:18 There was 20 people started on the day that I started and by week three, there was only about eight of us left. Sounds like a game show, doesn't it? It was some kind of Hunger Games, you know, Utopian World. And it was if you can't do it, you don't work here anymore. You know, again, learn a lot, but certainly.

38:47 certainly struggled in the early days with that role. Now you didn't jot that down as a highlight role. Is that because it was not long enough to worth talking about? It's a weird one because you could argue that that was the most important job in my career, but I couldn't bring myself to put it as a highlight because it was the worst job I've ever had. that well, you know, this is, this is good feedback actually for the

39:16 questionnaire that we sent guests maybe I need to change highlight forward slash low light role because I yeah we it feels like it's important like you just said because it was a low light so we okay we will spend it we'll spend a few minutes few minutes on so how long did you do that so I think I was there for no longer than eight months and we were we were struggling

39:45 in the northeast with kind of what we wanted to do with our lives. My wife about six months in to me doing the role got offered a job in London and we were like, okay, could this be something that we do? Which led me to search for sales jobs, London, again.

40:15 At this point, I don't even realize I'm in B2B sales. I certainly don't know anything about SaaS sales. But I'm just calling people about utilities every single day. Without doing that, I probably wouldn't have got my first B2B SaaS role. As you can imagine, when I told them I call 100 to 150 businesses every day.

40:44 I'm hitting target that was interesting and to yeah they were they were like so the guy sit next and they're like we found one we've yeah he found one yeah he this guy is a machine but obviously like it was a different it was a different mindset when I was selling utilities because it was like well if you don't if you don't do this you're you're kind of gone so yeah it was it was definitely a low light but it projected me on to

41:15 the world of B2B sales. And if it wasn't for that, I think it would have been very difficult to go from Apple retail to SDR in London at Hootsuite. I don't know if the gap would have been bridged enough. I can't remember what book I read this in, but it's the theory that you can't, happiness doesn't exist.

41:43 without unhappiness or good does not exist without bad. So for you to be able to list something as a highlight, you had to experience a low light. There has to be some sort of foundational benchmark of what bad is. So it is very, very important for people to experience bad and not be afraid of experiencing some of it. You haven't done something wrong if you've gone into a job and you hate it it's miserable. That's not, you haven't done anything wrong. It's good for you. You just don't, you don't know it yet. Okay. So, uh,

42:11 The moving to London thing that also seems to be quite a common trend for people that I've spoken to so far. Jack, for instance, up in Manchester. Well, actually, no, sorry. Jack was Jack moved. Jack was from London. It was Zach, I think, moved to London. Musicians. London seems to be this big magnet that pulls people in. So you.

42:39 joined Hootsuite, you've just touched on Hootsuite. you, did, was it that you came across it and it was just the first job that you managed to land? Yeah, I look back and I can't believe how little research I did on the SaaS industry. And I think about now how people are so switched on and we've got LinkedIn and people like know they want to be an SDR.

43:07 a year before they even get the role, right? I literally typed into Google, sales jobs, London. I'm working sales at the moment. Are there any sales jobs in London? And when I started as an SDR at Hootsuite, I literally had no idea what an SDR was, what an AEU was, what a CSM was. I didn't have a clue about the industry, the space.

43:37 So yeah, I think again, I always give myself a pat on the back for getting that job. Especially because I was just massively unprepared. They saw something in me which I was always grateful for to give me that role. One of the stories that I tell is I'd seen that we were gonna be doing a role play as part of the interview.

44:06 and they gave me someone who I had to pretend that I would call. But to prepare for the interview, I just really called the person who was in that role. It was someone at Tesco. I got through to him and I had a conversation with him. So when I was in the interview, they were like, we're going to do the scenario here. And I said, to help you guys out, I spoke to Terry at Tesco's last week.

44:35 And he told me X, Y, and they're like, mouths dropped because they were like, wait, you actually called the guy. And I was like, yeah, yeah, we had a great chat. And I look back and I think that really helped. You know, I knew I had to do something a little bit different to to get that job because that's one of those stories you come across online where the hiring manager goes, I've never come across this before.

45:02 How amazing was this candidate for doing this? And I, you know, I call it, and I joke about it in my content now, I call it a wow moment, you know. We used to do it Apple. What can I do to make people go, wow, that was great. And I knew I had that in the back pocket going into the interview because, I certainly wasn't the most clued up candidate for an SDR role. And I was self-aware about that.

45:31 So I had to have a I had to have a plan Right, so you moved on to London. You're looking for sales jobs. You came across a company called Hootsuite Did you have any idea what Hootsuite was and kind of the tool the platform? No, no and We did two weeks of onboarding and They said normally we fly people out to Vancouver I think it was and we do like two weeks. They said there's been a bit of a mix-up. We're just gonna do yours

46:01 in the room upstairs. It's just you and the trainer. And we're going to do it in a week because we, know, two weeks is a long time. Now, I, my wife will tell you this, I struggle with classroom learning. There's like a lot of information and I would like zone out in a lot of the training. I needed a coffee.

46:30 I would say to my wife, I nearly fell asleep in the afternoon and she was like, what are you doing? I said, I'm struggling, know, I'm really struggling with this like classroom, me and some, and I was going, know, okay, yeah. So yeah, I tell that story because when I got on the floor, was I clued up?

47:00 on the product in absolutely no way. I tried my best to listen and to learn, but no, was, no visuals, no kind of, there was no interactive element. was just learning from a slide deck and I struggled with that. I really did. The reason I'm laughing, chuckling away in the background is because

47:27 I always, I didn't know if it was an age thing, but ever since I've left university, uh, so the last, Oh God, getting a bit old now, 11, 12 years, if there is some sort of training session in the afternoon and you're just being spoken at. if it's honestly, if it's longer than 10 minutes, I just feel my eyes going. I physically, I feel the Twitch of like, I've just fallen asleep and I find it so hard pinch myself like this.

47:57 You know, to like, and I'm going, you're a grown, you're grown man and you've got this great job. But, I think it just, and again, to bring in kind of my sales coach here, it just shows the power of, um, you know, having that kind of one-to-one short sessions, um, where you can really learn and engage rather than it's going to be, it's going to be six hours. It's going to be every day. We're going to, we're to have a little break for lunch.

48:26 Yeah, I think a lot of people will relate to, or relate to that. I've heard that soldiers who have to, these big, you know, coronations and things, the soldiers that have to stand for hours, they will put a pin, a drawing pin in their boot and they'll just tap their toe on it to keep them awake. So there's a little future optimization there. A pin in the boot. Okay, right. So you...

48:55 I went through this week of onboarding and then I'm assuming it was, there's your desk, there's your phone, crack on. Pretty much, you know, my manager said to me, make sure that you log everything in the CRM. And I said, no problem. And I turned to the person next to me, I said, what's the CRM? You know, and that was where I was at. this, I remember the guy next to me going.

49:22 How have you got this job? Now obviously like I was really Northern as well, know, a lot of the people in the office were based in London and I did feel a little bit like a fish out of water. I had to kind of learn on the go and again went from calling these small business owners.

49:51 who might have even a corner shop, right? Everyone has utility bills to call in the C-suite of these huge companies, to speak into people who were in social media, like who had real jobs. was a learning curve, that's what they say, don't they? And how long were you an SDR at Hootsuite? What was the time span? Yeah, so again, I think that was...

50:22 Was it under two years? I think it was a couple of years. So again, struggle to kind of progress even in that role talked about being a...

50:35 customer success manager at one point. We got pregnant and ended up moving back to the Northeast in what can only be described as us yo-yoing up and down the country, which we seem to have done for the past few years. So again, that was a huge shift and a huge change for us and that was one of the reasons for leaving.

51:04 But two years is a pretty good stint as an SDR. If you pass the six to nine months thing, it's kind of like, you can be an SDR. So if you did it for nearly two years then, were you a successful SDR? you do well? Yeah. I I hit target and was able to do the role and to do it well. Found my feet.

51:34 you know, learned my kind of style of what works, realized that people like to get something for free. Like that was the beginning of me understanding, okay, how can I add value? Like the V word that we all use now. Hootsuite, did these assessments, know, social media assessments, and I could give you one for free. could speak to social media managers and say,

52:04 Do you want to know your demographics of your audience? What they're interested in? I'll give you an assessment. Jump on a call. Let's find out where they're from, what they care about. Like it was almost a no brainer for social media managers. They were like, well, yeah, I'll take that. I'll take that call. Tell me what you know. So yeah, that that helped me really. Once I clicked on that, I could add value to people and not just be like, I want to sell you a

52:34 products that that really helped. And then, I also had a bit of a mentor at Hootsuite who taught me about selling into the educational space and how universities really care about social media. Who would have thought, right, that's where that's where teenagers live, right? So they want you to know about their universities. Realizing that there was this

53:03 huge market for universities who wanted to be present on social. Again, that really helped me to have those conversations. was I good? Yeah, I guess I found my groove, found what worked, found an industry to sell into, which is what any good seller does, I guess. And you say you found out what worked well for you or what?

53:31 traits or skills that you had that worked well. So what were those for you at that point? It was humor, you know, it was calling out the elephant in the room that you're getting a cold call from a stranger. It was learning from years of what had worked on the phones. I used to sit next to someone when I worked for utility wise and

53:59 She was amazing, right? She was like in her forties and she would just be cackling on these cold calls. Like she was speaking to her best friend. And I was like, how is she doing this? So I listened to her calls. She was just making people laugh. She would just go, I'm going to make a call now and I want to make the person on the other end of the call burst out laughing. Now, when you do that, Jamie, something amazing happens.

54:28 You have an instant connection with someone and they, go, okay, what are you, tell me what you want to tell me what you've called for. So for me, that was something I did at Hootsuite, right? I would just call people up and say things like nobody likes, nobody likes a cold call, right? And, uh, I don't like making them. You don't like taking them, but let's, let's see how we do, right? Like disarming people, leaning into humor, all those kinds of traits that I still use now.

54:58 I would bring into that bring into that role and that that's what helped me be successful and The Yorkshire accent is the most trustworthy in the UK. So I know you've spoken about this before but like using your accent to your advantage Yeah, never kind of him Never liked my accent, know, I'm Always felt like it was too nasal and made me sound stupid but but actually and

55:29 in my early career and even now it seems to have been a tool, right? And we don't get a lot of gatekeepers anymore. That was not really a thing. when I was back in my day, I was a cold caller, lots of gatekeepers, right? So I could use my accent. You would be speaking to a really well-spoken person who's

55:57 you know, just taking calls all day long from maybe people who are senior or execs or very polite. And I would call and I would crank up the accent and I, you know, pretend I was a bit of a div. Oh, hello. Sorry, who have I got through? Sorry, who have I got through to here? Have I called? Have I called? What number is this? What did you say your name was? Sally. Oh, Sally, I'm trying to get hold of date.

56:26 David do you know do you know David right now that Sounds crazy when I've just when I've just done it there right, but you know what I? Would get through to Dave yeah cuz Sally was there like oh This guy I'm gonna do I'm gonna I'm gonna help him out because he said he needs help He certainly doesn't sound like he's a couple of buildings away working for a Corporation who's trying to hit his target it sounds like the milkman

56:57 who's got lost and ended up on the phone. I would like use that to my advantage. How did that go down in, I'm assuming your managers listened in to calls. So what did your managers say about it? Well, they would, mean, if I was hitting target, right, they would be happy with that. So I used to call it daft lad. I'm going to be, I'm going to call someone up, I'm going to be daft lad.

57:25 And that would be the persona that I would play. But I think like any sales manager, right, if the seller's bringing in the results, can do what they want. They can say what they want. And that's the thing I like about this whole space. There is no playbook. There is no set way. You can have someone on the phone who's playing it one way, someone on the phone next to them playing it the other.

57:52 You have to play to your strengths and do what works for you. So yeah, they were, they were very understanding and, certainly inspired me to, to play it that way, you know. Okay. So two years at Hootsuite, you said you moved back up North, which was one of the main reasons why you changed role then. So how did you come across your next position? Yeah. So when we panicked, got pregnant and panicked, right.

58:21 We're in London. We don't have family up here. Emergency red button back up to Newcastle where we've got family. Again, I was just like, I need to find a job. At this point, I'm a bit more clued up. So was like, it should probably be in the SAS space. I don't want to just randomly get a sales job. I need to keep my toe in the water. So I found a SAS company.

58:49 in Newcastle, were called Orchard at the time. They've been taken over now, think MRI, I think, if I remember correctly. But they were selling software into the housing sector. So they were calling like councils. And again, not something for me to get excited about, but the fact it was SAS was enough for me.

59:18 to take a job there. The office was on the River Tyne. There was a view of the bridge. I thought I could probably get lunch in the quayside. Sold. Ticks all the boxes. Exactly, yeah. I just thought, I knew I wouldn't be there for a long time. I knew we'd go back to London. So it was like, how do I keep a role that's in SAS? So when I...

59:48 for my next role, I'm not just a random person who's fallen out of the SAS space. So hang on, you went back up north and then back to London again? Yes. So how long was it? You went back up north just simply just to have kids? Kind of. We had Arthur. You didn't want them born in the South, that was it? We wanted to have a Geordie. like you say,

01:00:17 We got eight months in and we were like, we probably would have been okay if we'd have stayed in London. We might have panicked. And actually being a parent is something that, know, first time parents you think, how could I possibly do this without support? When you have a baby, you think, okay, something happens, right? Where you get into a rhythm and you get into a flow. So,

01:00:46 Yeah, we realized we'd made a mistake. We were like, we shouldn't have left, you know, London. That was a mistake. The opportunities are better down there. The salaries are better down there. I'll tell you that. So we moved back down to London again. They moving is one of the most stressful things, right? Blame it now. You've done a bit. I don't know what we were thinking, you know, and when we moved...

01:01:16 down in 2019 for my SDR role at Sales Loft. said, that is it now. No way. Eight months later, COVID hit and we moved back to the Northeast. So yeah, that ridiculous. Blimey. Okay. So you, you, mentioned Sales Loft there, I think for those watching listening.

01:01:42 That's probably where most people will first have come across you in terms of your content, because that's kind of where it all started, right? The content side of things. So you, I take it, it was a similar methodology of sales jobs in London, SAS, and you came across SalesLoft. A hundred percent. I mean, at this point, I know I need an SDR role. I'm a bit more clued up about researching organizations. So I'd found, again, the timing was perfect, right? I found a SAS company.

01:02:12 who were launching in a mirror a brand new London office and they were hiring 10 people. Two of them were SDRs. So it was almost like right time. I knew the company were a good company. I'd done some research on them. So I knew I needed to land that role. was like, this is the one for me to get. Headed down to London in a suit and tie with the shoes that I got married in.

01:02:41 So only wore them twice, once to get married and once for this interview. Turned up, I met Ollie Sharp, who was wearing a hoodie and jeans. The first thing he said to me was, you can imagine how uncomfortable I look, right? I talked about being an extra. He said, do you always dress like that? I burst out laughing and said, no, I only wore these shoes twice. I've just dressed up.

01:03:11 Like the, the, kind of facade went like that. But I was so grateful that happened because I just instantly relaxed and I was able to go, okay, I think this, hiring manager, um, might be on my, my wavelength. I've, um, I've, I've never burst out laughing 10 seconds into meeting an interviewer before. Um, I've never felt more comfortable. Um, for those who don't know Ollie Sharp, he was at LinkedIn.

01:03:42 Previously and I was like, oh I need to be Super professional this guy works at LinkedIn like I again self-confidence. I'm just a moron from from the north and Turns out he was from Yorkshire originally and We got on like a house on fire and it was again. It was for me. It was just meant meant to be that that that moment, you know Okay, so and was it

01:04:11 From that point onwards, was there any easy job to get because you sort of you had some rapport with him and did it just go well in the interview? Yeah, I mean, I don't know how I don't know if any job is easy to get. And it was made clear to me that there was three people in the kind of final stage for those two SDR roles and. Struggled a little bit when I.

01:04:41 had to have Zoom calls with the team in Atlanta. They were like, we're going to put you on with some of the team in the States, right? I had never really even spoken to many American people. And I was on a call with a guy who was spinning an American football. He was a jock, right? And he was kind of leaning back in his chair.

01:05:11 And I was like, Oh, hello. You know, I'm from England. And I remember being like, I might have lost this interview because I'm talking gibberish. What am I, you know, what am I doing? Do the team like me? Did they just got off that zoom call and be like, you know, who the hell was that guy? So that was a, that was a moment where I thought, is this going to, is this going to jail? So I don't know if it was easy to get, but yeah, it felt like, it felt like the job I was meant to get, if you like.

01:05:40 And as I said, I this is going to be a good, interesting conversation because this is where your content journey, least in, at least in SaaS started. So first give me, give us the rundown of the first few weeks and months then, because it wasn't long. I mean, I know this already, but it wasn't long before you started thinking about making content, was it? Yeah. So I'm in a room of 10 people. We've all been hired and I've been given the kind of role of my life.

01:06:10 Right. And I knew based on everyone in the room that I was probably the least qualified. I'd also say, Jamie, that everyone seemed to know all companies in London. So someone would bring up a company, right? We're talking to Chair, you know, Chair Inc. And everyone would be like, oh, yeah, Chair Inc. Their CEO is Mark, you know,

01:06:40 Mark Smith and I'm going who the hell is Mark Smith and how does everyone know about Chet Ink? So it was like I was like panicking right and also they were all good on LinkedIn you know you had Jack Nico to my left who was who was kind of present on LinkedIn, Misha Jessel Kenyon in the corner who was posting on LinkedIn, Ollie Sharp who'd been at LinkedIn

01:07:09 And I was like, my LinkedIn is me in Newcastle doing videos of the river Tyne or sharing information about councils, because let's not forget, I was selling into that space. So again, it was a bit of a panic moment where I thought, I need to use LinkedIn more than I've ever used it before. I didn't even really use it at Hootsuite. I was like,

01:07:38 Everyone's using LinkedIn. Everyone's posting on LinkedIn. It felt like the thing to do. And also I'm directing people to my profile, right? We were using social selling more than I'd ever used it. In previous roles, the cadence was you give them a ring, you send them an email. That's what you do. At Sales Loft, it was like, no, no, no, no. The first thing you do is you connect with them on LinkedIn. So again, I was like,

01:08:06 My hand was forced a little bit. was like, well, I can't direct them to this profile. It's terrible. And also there's nothing on my profile that sets me out as any different. So yeah, people in the room were posting about their insights and all the things that they knew about sales. I thought I will do the same thing. So I started to film content, which was me talking to the camera.

01:08:36 And I would tell LinkedIn about sales. So yeah, that lasted for about, for about three, three months. Those videos are still there before I got frustrated and thought, I'm just going to, I'm just going to have some fun with this and start making, start making content that, that I would like to watch. when you say you, so you did that for three months. I think we all know that sales people shouldn't just pitch, right? They shouldn't.

01:09:06 just go in with the hard sell and whatnot. So what was, tell us the story of your first ever piece of the new style of content. Yeah, I I'd just been picking up the camera and like going, right, what does SalesLoft do? Okay. What are our core values? Okay. Right. That'll be great. So I'd hit record and be like, here at SalesLoft, one of our core values.

01:09:36 And obviously I realized nobody cares about me. Nobody cares about the company, which was hard. That was hard to kind of swallow. So I was like, well, I'm great. And the company's not too bad either. Right. You know, I've picked them for a reason. So the kind of new style of content and the first video that I did that sort of went viral. I did a sketch or a skit on excuses that sales reps give.

01:10:05 for not filling out the CRM. I'd given all these excuses before, don't worry about the CRM. I've got everything on a spreadsheet. You can't see the spreadsheet though. It's a secret password protected spreadsheet, but it's all there, know, so don't worry. Or maybe the rep would say, it's got lost in the cloud. So I did it yesterday, but it must be, it must've got stuck in the ether.

01:10:35 you know, in the cloud. And then at the time Salesforce lightning had just launched and my colleague didn't like using it. So I sort of picked up on that. And I was like, I've not filled out the CRM because I can't use Salesforce lightning. It shouldn't be called lightning. It should be called frightening because it's scary. So I posted this video and it just blew up and I got like

01:11:03 100 plus thousand impressions and again I was just like okay that's that's the content then I'll I'll just make content which is relevant to the people I'm selling to highlights either a problem or something they've gone through and I'll use humor to tell the story and been doing that for five plus years now

01:11:32 And because you joined in as an SDR, but you made your way up to brand awareness manager and there was obviously this natural shift from sales to more marketing. So how long were you an SDR producing that sort of content before you started doing it before it started becoming marketing and not sales? Yeah, well, I was, I was really getting into the, to the content, right. And I'd started to build a brand. Um, I was like, this is great. can create videos, use that as part of my outreach.

01:12:02 got to a stage where I'd ring people up and they'd be like, oh yeah, I think I've seen a couple of your like funny videos. So that was about six months, eight months in. Then that was when COVID hit. And I was like, I don't think it's appropriate for me to be making these videos. know, you remember, and when COVID first hit and everything just felt like really, can we even like laugh anymore? Is there a place for like humor? And after a couple of weeks, I realized

01:12:32 I think this might be more important for me to do than than ever before. So I started to do the we're all working from home style pieces of content, the sort of covid era content. And that kind of outperformed the other stuff that I was doing. So again, it made me realize that. Yes, you have to do things that are relatable, but if you can create content that's of the now that people are going through right this second.

01:13:02 you know, that can really get you traction on on LinkedIn. So, couple of years again, everything I do is a couple of years, but a couple of years into that role. And after I'd built a significant brand, there was a conversation internally, you know, could this be something that Tom does as part of a marketing role? Could this be a brand awareness role?

01:13:31 we get into do this kind of full time and I was very lucky that that became my full time role helped massively by the fact that everyone that I spoke to in the organization said Tom you are mentioned at every stage of every deal that we do at Sales Loft so like when you get that feedback it's like how could you not go into a

01:14:01 brand awareness role because people are doing your job for you by saying, I see this guy everywhere. I've got in touch because I've seen the content or I love what he does. Like those kinds of conversations helped me to get my promotion. Um, okay then. So you, this was your first sort of foray into marketing, having pretty much been in sales roles your entire career or sales roles of sorts then.

01:14:30 That must've been a bit of a not having a number attached and not having to make certain number of dials and fill the pipeline with deals and do deal management and stuff. So was that a bit of a shift for you? Yeah, I mean, every seller or every SDR, should I say dreams of the day, you know, the magical day when there is no pipeline, there is no, you have to do X, Y, Z.

01:15:00 These are your targets. This is what you need to hit. And I thought that, yeah, joining marketing would be the end, the end of all that. And then all that happens is you realize we just have different kind of targets and we have different goals and you need to be as consistent as you were in in sales, just in like different, different areas. It certainly was a shock and a shift, though, openly. And I said this to the team.

01:15:29 I'd, everything I'd learned about marketing was self-taught. And I certainly wasn't an expert. So I had to learn a lot from, from the team and still find myself in marketing now, but you know, openly don't really have a marketing background. I'm a sales guy at heart, you know. You transferred into this marketing role and then I cut five years, was around five years you were at sales loft.

01:15:55 So you did the marketing, the brand awareness manager for three years. Let's talk about that three years then. you, you, they were like, right, we, we can see the value in what you're doing. We're to move you into this dedicated role. So 40 hours a week. Now you were content, brand awareness, but you were creating content. Yeah. So I was, I was hosting the podcast for, for sales loft. was creating content and then training the.

01:16:25 the internal team as well. So I led a group of about 30 at sales loft who wanted to kind of build build their brands. But content was very much at the heart of that role. So you were you kind of went back to that Apple specialist workshop style stuff as well internally. Yeah. It's funny because, you know, there was almost like some slumdog millionaire moment where

01:16:53 I realise that everything I tried to do in the past came together. I tried to do radio, which didn't work, and I found myself doing a podcast. I tried to do a YouTube channel, recording myself doing content, which again, nobody liked because it was just me in London filming myself, like who cares? And also I'd done this kind of coaching training.

01:17:22 Apple and then suddenly I was doing all those three things and in one role and really enjoying it so and Yeah, it was it was kind of strange really it was a bit of a pinch me moment where I was like Was this like meant to be you know was was all this experience kind of leading me to this to this role and And I think it was I I really do yeah, because you said earlier in the conversation that you

01:17:48 didn't really know what you wanted to do and you felt like other people had discovered what they wanted to do and they were progressing. was it that moment when you were like, ah, I think I might've found, I think that things have fallen into place and this is what I should be doing. A hundred percent, you know, my whole career, basically, from Wix right up until Orchard, know, everything in between, everyone had always said to me, oh, you're wasted here.

01:18:18 You're wasted here. And they thought it was a compliment, but it was not. It was quite hard to hear because you kind of think, am I wasting my talents? I knew that I had the ability to make people laugh. Like, humor has always come easy to me from an early stage, even at school.

01:18:46 It wasn't something I had to work on. was just like, OK, well, this is this is a funny thing to say now. This is a funny thing to do. It just kind of came naturally. So, yeah, to be told your whole life, oh, you're you're wasted here. That was that was tough. And it was the first time in my career where people had stopped saying that people started saying it feels like you're in your lane, Tom. And I was like.

01:19:15 What a great thing to hear from someone, you know. Yeah, I think it must have felt a bit of a. I don't know. Did you have like a baseline anxiety of still not having figured it out? And then once you went to the penny, you dropped, you were kind of like. I can just be myself and like relax basically. Yeah, I mean, that's all that's all you want in in life, right, to be able to to be yourself and to enjoy what you.

01:19:45 what you do and there is nothing worse than kind of feeling like not only am I not really being myself, I'm just kind of like doing the role where I'm ticking the boxes but I'm also not enjoying it and I might feel like I've got more to give. Like is there a worse feeling than thinking, oh I've got more to give than this, know? Sweeping up cigarette butts in the Wicks car park in a high vis jacket.

01:20:14 I think I've got more to give than this, you know, it's a, it's it's a tough, it's a tough feeling. But it is also a motivator. Yeah, a hundred percent. And I think that back to that Ica guy thing, that's the mission thing of having some sort of purpose rather than you sitting in the car park going, there's got to be more to life than what I'm doing right now. So I, couple of questions on, on that three year period then, like the brand awareness manager.

01:20:44 I guess the first one would be, give me one of your, a couple of your favorite videos that you've done that either did really, really well, or you just loved doing, what were they? The one that springs to mind, it was a call I was on with a colleague of mine. And because of the timeline in Atlanta, I tended to be on calls like five o'clock, six o'clock in the evening because it was

01:21:12 much much earlier for them and it was the winter time right so I was in the garden it was really dark and I'd I switched the lights off by accident and I was just lit by the laptop screen and I sort of looked like I was in the wilderness or like the Blair Witch project and and my colleague at the time said you should you should do a video on with this lighting and about like sales

01:21:42 being like a wasteland. that evening I recorded a video filmed by the light of my laptop. I did some tundra sound effects like I was in the North Pole and I wore a huge coat and delivered every line shouting and some of the lines from that video were the fact that

01:22:13 all the marketing leads had been burnt for warmth because we're struggling so much and little dig at marketing which I like to do. But yeah, describe sales as a frozen wasteland and if anyone goes out there, they don't come back, you know, that was one of my favorite videos.

01:22:39 We've spoken about this, it feels like throughout actually all of your roles, which is really, really nice is that you started layering on people or layering on this thing where if you were yourself, you did well. So in terms of settling into something you were good at, tell me about how that built confidence. Cause we discussed previously how...

01:23:05 We've both struggled with imposter syndrome. We've both struggled with a lack of confidence in that three-year period must have been really really good for just affirming that level of being yourself Yeah, I mean, you know I I can be a bit weird and My wife will say that you know, I'll I'll do things which are a bit quirky and I've I've tended to like rain that in a little bit

01:23:34 But actually with content creation, sometimes that's a good thing, right? You stand out from the crowd, oh, that was a bit different. Oh, that's like a different idea. So yeah, leaning into that and feeling like you do have the freedom to give your own opinion, to tell your story in your own way. That has definitely helped me. And there's nothing better than receiving comments of encouragement, people saying, oh, you're...

01:24:03 You're my favorite LinkedIn creator. That makes you go, well, that's so nice because I'm, you know, putting myself out there, getting that encouragement, a bit like the MPS scores, right? Still need those compliments. Makes you feel like less of an imposter. Makes you think, well, actually, maybe I'm doing exactly what I'm supposed to be doing. we took, Apple, was the MPS score. That was like a metric. So give me a couple of metrics then. So not.

01:24:33 Not that the metrics matter in terms of followers or anything like that, but you were brand awareness. So they kind of do in a way. How many followers did you build up during that period? And could you have a rough idea of how many impressions you were driving a year through your content? Yeah, I don't think I've ever kind of formalized that, but when I, when I got my role in marketing at sales loft, was probably on

01:25:01 15,000 followers and and when I left I was on 55,000 Followers so yeah gained gained like 40 in those in those three years and the impressions and it's so funny because Impressions on video has has gone like through through the roof in the past six months so my impressions weren't

01:25:31 probably as high as they were now. But some of my top performing pieces of content whilst at that role would be like 600,000 impressions. Blimey. Okay then, so before we jump into your next role, all good things have to come to an end. So just tell me why after five years you felt like you needed something new.

01:26:01 Yeah, I mean, I think you've kind of answered it there, right? Five years in, making content about the same platform, talking about similar ideas. And it just felt like time for a change. Working remote in the garden in Gateshead.

01:26:28 you know, not being around the team, being so far away from London, rarely going down because of responsibilities with my family. So not really seeing the team out in Atlanta. Lots of changes in the company in terms of like direction and tone of voice. These were some of the decisions that made me go, I think it's time for a change.

01:26:57 which brought me to my sales coach, right? Just over the river in Newcastle in an office with real people to get me out of the garden every now and then and to talk about one of my passions, which has always been a passion coaching. And you know what, for someone who seemed to move between the North and London every eight months, five years is quite a long time. Yes. Yeah, we...

01:27:27 We definitely settled COVID, COVID forced our hand and we bought a house and it was like, no, this is where we live. This is where we live now. We stopped, we stopped messing around basically. Okay. So any of those watching will have just noticed a sudden change in outfit for the both of us. We weren't happy with our style. So we thought we'd get in the pros and this is what we're going for for part.

01:27:54 part two, which is probably only going to be about 20 % of the recording. But Tom's in a different room. He's got a blue shirt on. I've got a different hoodie on. Still the same great content. Just bear with us. back. Well, I say welcome back, but this is the same episode just three weeks later to record the second part. When you get to a certain level, you need a costume change. You know, it's it's a, it's a.

01:28:17 Come to be expected. Yeah. Big budgets. see stream at deal front. got millions of pounds a year to throw out this sort of thing. We haven't stretched the makeup just yet. That's the next thing. The end of the last episode, we got up to the point of you moving to my sales coach. think you said across the river, uh, was how you, how you introduced it back into the office, doing what you do or doing what you love, which is coaching. So tell us about, uh, your

01:28:44 I guess the fundamental reason why you decided to take this particular job. Yeah. Well, it wasn't just proximity. mean, am just, just, just over the river. I'm based in Gateshead and I'm, I'm here in the back garden of my, uh, my house in, Gateshead and the, sales coach office conveniently is in Newcastle. So not too far at all. If I compare that to jobs I've had in the past at Sales Loft, where the office was in London.

01:29:11 you know, 300 plus miles away, little bit tougher to commute to, right? Not something you want to make a habit of doing, at my sales coach, I can just pop in and out, which I quite like. But ultimately, you know, it was me seeing an opportunity for a role where I could, you know, not only create content, which is a really big part of my role, but actively coach.

01:29:41 people who were kind of where I was a few years ago, right? You don't have a brand on LinkedIn. You're not using kind of social selling. You kind of know it's a good idea, but you don't really know where to start. I'd been working as a coach with my sales coach as a kind of part-time basis for eight months before I joined. And when this opportunity came about for a full-time role, which would incorporate

01:30:10 the coaching on a full time basis, the content creation, and also looking after all things brand. I was like, I mean, you know, I, uh, I love that. I love that team. We've got a fantastic team at my sales coach and then yeah, what's better than helping people to kind of realize their dreams and goals and, and getting them to move forward in their career. Quite, um, quite relevant for this podcast, right? Um, I.

01:30:39 I really have a passion for that and I've really enjoyed not only building my personal brand, the brand of the business, but then also coaching sellers and sales leaders around the world too. And what sort of coaching do my sales coach offer? I mean, is it broad spectrum, anything and everything to do with sales? Yeah, well, I focused on the coaching that I deliver, which is social selling. But one of the kind of unique things about my sales coach is we have all that

01:31:08 80 coaches and everyone has a individual expertise so I'm doing a of a plug here now but when you know it's interesting it's interesting when you become a customer you get matched right to could be one coach could be two could be three that are gonna help you to achieve your goals so if you are wanting to build a personal brand you're probably gonna land with me but if you're a CRO who wants to talk about building the

01:31:38 GTM strategy, it's probably not going to be me funnily enough, it might be one of some of our other coaches who've sat in seat as a CRO for maybe 10-15 years right, so it's kind of leaning on the expertise of people who've done what you've done, who've been where you are but are kind of where you want to be.

01:31:59 Interesting. Okay, so we typically ask what you've learnt in the role. You're still there, so you're still learning, but what have been some of the highlight things that you've learnt moving into that more dedicated brand role where that's the only role you've had at that company purely brand? So what have you learnt so far? Oh, well, I could probably really delve into this one. I'll start with the challenges because they're normally the fun ones, right?

01:32:28 Um, it's the first time I've been solely responsible for a LinkedIn brand page. And that is difficult, right? For someone who has really found a rhythm with building a personal brand, managing a LinkedIn brand page is tough, right? Engagement is low and building followers is hard. It's demoralizing, isn't it? It is. It is right. Especially for someone who

01:32:56 Like you say, I've built almost 70,000 followers. I mean, I'm definitely in a rhythm, but no, it's been a, it's been a, know, bucket of water to the face with the, some of the engagement levels of my one to two likes on a post that I've done from the brand page. But also I've really embraced that, right? And I've kind of gone, okay, well, how can we give this brand page a voice? I managed to double the follower count since joining, but still really getting my teeth into it.

01:33:26 what does a good LinkedIn brand page look like? So that's definitely been a big learning. Also my sales coach, right, is a lot smaller than Sales Loft. So going from a team, which was huge, I think over nearly 800, think, when I left, maybe more, 100 in the London office, we have 20 at my sales coach. Most of them are kind of remote.

01:33:55 So super small team, which comes with its own challenges, right? When you're a startup, you do a lot of things internally. I'll give you an example. We had a conversation recently about a new website and I was giving all these really kind of grand ideas about the site and everyone was loving it. And I was kind of giving all of my ideas. And then it kind of slowly dawned on me that...

01:34:23 these weren't ideas that we were going to give to someone else. We were doing the website internally, right? It was kind of our responsibility. And a lot of the ideas that I came up with in the meeting, I ended up becoming personally responsible for, which was a bit new for me, right? Because I was a bit used to that kind of larger organization mindset, you know, a bit more kind of maybe enterprise organizations where

01:34:53 or we'll just outsource that or we'll just allocate. Yeah, he's 300K for a website. This is it, right? Yeah, yeah. Big time. I mean, that's cheap. That's nothing. But you know what I mean? was one of those things where I've kind of gone, OK, wow, this is going to be a lot of kind of in the trenches, kind of, yeah, they say, don't they, building the plane as we fly it. But I've loved that, you know, and actually seeing.

01:35:21 the website went live a couple of months ago, seeing that go live, sounds silly, I'm gonna sound silly, I got goosebumps when the website went live. I don't think I'd have got goosebumps when the website went live if we'd have outsourced it, you know? So it's just- You feel less of a cog in the machine and more as a founding member. That's Yeah. Makes you feel that, yeah.

01:35:48 Okay, here's a couple of questions then. So one question on the LinkedIn side of things, what would be your single biggest learning in terms of building that engagement on a company page? Because my team sort of, I say look after social, we don't have a dedicated person looking after social, but we're always thinking about ways that we can improve engagement and try and scale things, improve things. So what have you noticed is the biggest win? I don't know. Yeah, biggest win so far on the company page.

01:36:18 Yeah, well, I've certainly learned that similar to a personal page, right, content thrives with the the comment section. So, you know, you can get as many likes on a post in the as you'd like, right? You could get a couple of hundred likes on a post and it not really reach a wide audience. If you get a couple of hundred comments on a post, different story, right? Absolute game changer. A post with 200 comments will probably get

01:36:48 five times the impressions of a post with 200 likes. So that kind of mindset of look, how do we create content which is audience focused, audience centric and prompts conversation and opinion. I think a lot of people do this with personal brands, but also company pages think that they are the solution, especially brand pages, right? We are the solution. Let me tell you about the solution. Let me give you the answers. Well, that's not gonna...

01:37:18 boost any comments, right? You're not gonna prompt comments from someone just telling you they know everything. But what my prompt comments and engagement is asking questions and asking people their opinions and not on the solution on the problem. So that would be a big takeaway for me. know, creating content which sparks conversation about the problem you solve will drive more engagement than a post about an update of your product or service.

01:37:47 Great great tip. I'm now sitting here thinking right. How can we rewrite all of our posts? So they're question-based Okay, and then the second question was the website. What was the you said to write all of these? Sort of big ideas like blues blue sky thing in or whatever what were out of the box? What were the what were some of those ideas just? Yeah, well our our website and I will I will say this with truth and honesty it was it was it was crap

01:38:17 It was it looked like a kind of a school website it was all white and It had a bit of text on there and what we wanted to do was bring the website to life so one of the things we've done if you go on our homepage my sales coach comm and you'll see rich our One of our traffic of his job title he's a

01:38:46 Don't worry, Rich, he still loves you, just doesn't know your job title. Head of growth, yeah. I didn't want to say marketing, I didn't want to say sales because he kind of does everything, but Rich heads up growth and you'll see a video of him telling our story. And in that video, you can navigate pretty much most of the site and almost take yourself on a video journey. Now, I, as you know, love video.

01:39:14 And often websites do feel a little bit bland. But one of the things I'm really proud about is that, you know, we've got customer videos, success stories on there, but we've also got the team just walking you through like how we work and kind of what that looks like. And I believe kind of video storytelling. And I know that you're a big believer in this as well. We'll do a lot better than just some text and some pictures. So again, that's one of my favorite elements.

01:39:43 Yeah, no, we've we've we're testing a new homepage variant. As we speak, actually, we got two week test running and we're using like way more color we're using. We're actually bringing the resources, the videos, the plays, the stuff that people find useful. That's now featured on the homepage. And it wasn't before it was all like value prop, value prop, value prop. It was sale, sale, sales. And now it's more value led. Yeah, we brought in the testimonials that you've mentioned there. So, yeah, I just had the site open in the background and I saw Rich in the bottom left.

01:40:13 It's a nice little touch that. Okay then, so we would typically ask why did you leave, but we're not gonna do that because you're still there. So we'll jump into the roundup. So this is kind of like a summary of everything we've spoken about so far in your career. So the first quick fire question, top three tips you would give for someone looking to progress in their career.

01:40:38 Yeah great, the one that springs to mind straight away is honesty. Being honest with yourself but also the people that you kind of work with right. I think a lot of people think that promotion and success is going to kind of just fall on their lap if you like, whereas actually if you're

01:41:07 honest and open about your ambitions and your kind

01:41:15 passion for getting a promotion and moving on in your career, you're going to open up those opportunities just speaking to people all the time. Early on in my career, I never said boo to a goose. I was very keeping all inside, never talked to my manager about progression. Always just thought, well, I'll just kind of do my job and hope for the best. And if I could go back, I'd be like, look,

01:41:45 lead with honesty, talk about your ambitions, talk about where you want to go. So that'd be the first one. The second one would be figuring out where you want to go and we've learned from this episode that it's not always linear and you can kind of go left, right, up, down. But discovering that, right, and I hate the phrase do what you love because some people are in a role going look I'm doing what I hate, right, but I've got a mortgage.

01:42:15 What I would say is, look, what are you good at? Right? It's like, start with that. What are your strengths? If someone met you, if you spoke to your partner or your family or your mom or whoever it may be, and they said, what is Tom really good at? Whatever they say, whatever the first thing that comes out of their mouth, if you can do for a living,

01:42:42 something that's centred in what came out of their mouth, you're on the path to success. You'll probably be happy, you'll probably be fulfilled. So like, you might not know exactly what you want to do. And 10 years ago, if someone would be talking to me about LinkedIn content creation, I'd be going kind of like, what are you talking about? Right? Cause I didn't even know that existed.

01:43:12 But we probably have a conversation about video, comedy, humor, storytelling, because these kind of things I'm like passionate about. yeah, give as my second tip, reflect on what you love and try, it's not always possible, but try to bring that into at least your journey in some way. know, it might not be the perfect role, but again, much better to be on that path than kind of nowhere near it.

01:43:42 And then thirdly I would say get a mentor, have a coach. A lot of people ask me where to get a coach. My sales coach is a great place to start because not everyone has that network. And I hate this story, Jamie, where people will say, oh, I just know a CEO and he became my mentor. And then that opened up.

01:44:11 You know, for someone like me, working class background, who doesn't know CEOs, right? Who worked in the DIY store. Actually, you're not going to make those connections. You're not going to find that kind of mentor. So a kind of quick path to do that is to work with somebody who can put you in touch with someone who's kind of where you kind of want to be and can be that kind of one to one. So yeah.

01:44:39 having a mentor but knowing where to find it really important. Three things. I've got a really good image in my head of people not in the UK, perhaps even in the southern parts of the UK, not understanding what boo to a goose means. First of all, that's brilliant. Number two, I think it reminded me when you were talking about making sure that you've got something that you love. It reminded me of the Japanese Ikigai, which is the

01:45:08 balance or the purpose of life and it's a perfect balance life in terms of this Japanese methodology of Ikegai is what something what you love what you're good at what the world needs and what you can be paid for and it's like finding the balance of all of those that would give you like a really really good career basically and then your last one the mentorship yeah it kind of made me think of like basically every prime minister's been from Eton

01:45:36 And it's just like, yeah, yeah, yeah. Unless you're born into it and you go to Eaton, how would you possibly have the connections that you get to Eaton, right? The schooling might not be, I do believe like private schooling. I don't think it's necessarily way better than public schooling, but the connections that are available to you in those schools, I think that's the added value. And unfortunately not all of us are born into.

01:46:02 uh, eaten families and have mates of mates and you know, with hundreds of millions and that sort of thing. So like you said, leverage, uh, things like my sales coach or leverage, um, connections you have on LinkedIn and ask for the intros and things like that. So that's some, yeah, some great advice. I think LinkedIn is a, a huge one, right? And you're, go onto LinkedIn right now and you see these people, even someone looking at my profile, right? Or look at, or look at his followers, look at his connections, uh, other influencers.

01:46:31 commenting on his posts, like I let myself into that party, right? I didn't know anybody and nobody knew me, but being consistent on the platform has allowed me to create those connections. And I'd like to say Jamie, that I'm quite well known now in our space, right? And that's been something that I've built up over the years and it's something that anyone can do. It might seem like, okay, well actually no,

01:47:00 can't do that yes you can there is a seat for you at the party go and take it go and grab it don't let somebody else take an opportunity that you didn't because they had a bit more confidence and what was the quote I saw the other day there are people who are way under qualified doing jobs right now that you would dream of doing because they had the confidence

01:47:30 to not be scared to fail. And I was like, that is amazing. know, that is amazing. You can be as smart as you like, but actually if you're not smart enough not to be afraid, then it's wasted. It is wasted. Stephen Barlow talks a lot about failing often, but fail fast. So failing often is good because you're learning, but don't fail for a year and a half before you realize that it was a failure. Fail fast.

01:47:59 Okay. This isn't working. Move on. Um, which is, which is really, great. So any regrets then that you have of your career today? Yes. Plenty. I, uh, I was the first person to say that. Yeah. Most people go, don't have regrets in life. I regret everything. Um, I was, I was, I was brought into B2B sales, kicking and screaming, right. Uh, my wife, and she'll tell you this.

01:48:29 pretty much had to force me in to the door of that first role, right? I was happy working in retail and being told by everyone in the Apple store that, Tom, you are so funny and I've really enjoyed buying this iPhone. Thank you very much, I've had a great day, right? I was pushed into, well, actually, Tom, you know, there's a potential for more and like, know, weddings are expensive, like, also, like, what are you gonna do with your life?

01:48:58 I wasn't happy, you know, and I look back on that and my wife often gives me this face which is that kind of like well, you know, I was the one who kind of Prompted you what you know some say inspired but it was very much prompted to kind of go into that world and I I regret I regret my attitude and I regret how much I complained because those early and You know days and days of cold calling and

01:49:28 rejection, they gave me my fundamentals of sales and they made me who I am really. So I regret 100 % moaning, complaining, going home to my wife and saying I don't like it, nobody wants to buy gas and electricity, it's hard, it's difficult. I should have been so proud to be doing that role.

01:49:56 if I'd have known the journey it was going to take me on. So certainly that. And then, yeah, as I kind of touched on there, right, I look back at my early career, especially as an SDR, and just just wasn't vocal, you know, didn't make connections, didn't talk about promotion, just just kind of see what happens, right, try and try and kind of do well. Didn't build a brand, you know, I was in there.

01:50:25 the SDRC for two companies over two and a half years and didn't build a brand on LinkedIn. And that was a huge mistake because I would be leaps and bounds above where I am now if I'd have done that a bit earlier. so yeah, gratitude, you know, being humble, you know, we all make mistakes and then yeah, not seizing opportunities early on.

01:50:50 Yeah, I'm glad you said the word gratitude there because it made me think about journaling. I do journaling and I've actually I went into it thinking journaling, a rubbish. You're just writing down pointless. But I do it every day and it's the right three things you're grateful for. And I think that's my the most usual part of journaling for me is actually like you can be grateful for sunshine. You can be grateful for a lovely meal that you cook yourself. You don't have to have

01:51:20 You don't have to have these big, big things happen to be grateful for. And I think I would definitely recommend doing gratitude exercises journaling for people. Um, cause it really does reframe your mindset and how fortunate you are to have a job that challenges you so you can develop and grow, et cetera, et cetera. And some people don't have jobs, uh, you know, um, right. We, uh, we're, we're up to time. So I just want to say thank you to anyone who has listened, who has watched, if you haven't done so already, please like follow, subscribe, whatever channel you're on.

01:51:48 And thank you Tom for spending an hour and a half, hour and 40 minutes, whatever it ends up being, chatting through your career. Enjoyed it. Yeah, enjoyed it. We went through a lot, didn't we? But thank you so much for having me. We did. And this will be episode one of season two. So there's plenty more episodes to come in season two. So we will catch you in the next episode.