Episode 1: From Fashion to Sales with Kaitlen Kelly

Kaitlen Kelly on Navigating a Sales Career.

In Meritt's first podcast episode, CEO Will Koning interviews Kaitlen Kelly, a sales expert, and advisor, about her journey into the sales profession. They discuss Kaitlen's transition from the fashion industry to sales, the challenges and rewards of the field, and the importance of resilience and taking risks. Kaitlen shares advice for those considering a sales career and highlights her personal growth and achievements in sales. The episode emphasizes the value of betting on oneself and the diverse opportunities in the sales industry.

Highlights

00:00 Introduction to Meritt's First Podcast

00:23 Meet Kaitlen Kelly: From Fashion to Sales01:18 The Journey to Becoming an SDR

04:29 Overcoming Challenges and Building Confidence

05:47 Taking Risks and Career Transitions

11:43 Advice for Aspiring Sales Professionals

15:56 Kaitlen's Favorite Quote and Final Thoughts

19:20 Shameless Self-Promotion and Farewell

Will Koning: Hey everyone. My name is Will Koning and I am the CEO and co-founder of Meritt. This is Meritt's very first podcast where we get to talk to sales professionals about how they ended up in the sales profession. Our very first guest today is a good friend of mine, Kaitlen Kelly. Kaitlen has been advising us over at Meritt on how to be exceptional salespeople, so I thought it was only fit that Kaitlen would join us for our very first session. How are you doing today, Kaitlen?

Kaitlen Kelly: Hey I am doing fantastic. Super excited to chat with you today and talk a little bit more about sales and how we ended up here.

Will Koning: Yeah, amazing. So we're here to talk to those people that have never really been in the sales profession. The first question that, that I want to ask you today, Kaitlen, is the question that my mum and dad asked me all the time is [00:01:00] why aren't you a doctor or a lawyer or something respectable, as opposed to being in the sales profession, how did you get here?

Kaitlen Kelly: Yeah, I think that's a super fair question. And I think the irony behind that is I think that's probably like the old school view, right? Is sales really respectable? So a little background on me is I did go down that more traditional path, went to university, got into the corporate career job.

I was studying within the fashion industry and did that for about seven years. And throughout that experience within this, the fashion industry, I had dabbled a little bit in sales, so that was a hundred percent commission based model. But even prior, if I go back to even before university my dad owns his own company, and so I was cold calling at the age of 15 without even realizing I was cold calling to earn some money on the side throughout high school. So when people ask, like, how did I end up in sales? I think it's something that happens on accident or you're, [00:02:00] you don't even, it's almost like an untapped gig or role. Like you don't know the potential within it because we don't really learn much about it. So as I went on the more traditional path after seven years within fashion, I was looking around, I was in an analyst role in the buying office and I just wasn't fulfilled. I had this like fire within me, I knew I wanted to do more and I had a couple of friends who had made the switch over and I was always terrified of making the switch because I was like, there's no way I'm going to sit at a desk and cold call all day. That is not what I'm going to do at all, and so you just build up these ideas in your head. And then, yeah, after seven years doing that at 27 years old, I was like might as well bet on myself and take a risk here and see what this is all about. So I made the switch over and started out as a, as an SDR outreach.

Will Koning: Yeah. So just for those that don't know what an SDR is, Kaitlen, tell us what an SDR is.

Kaitlen Kelly: Of course. So an SDR is really that entry point [00:03:00] into a sales career. It's a Sales Development Representative. And what you're doing is you're really focusing on generating top of the funnel pipeline. It's a great way to get into, it's like building that foundation before you jump into an account executive or closing role, because it's going to allow you to learn your business acumen, how to prospect and get a lot of those key skills that will accelerate your career long term.

Will Koning: Excellent. If we just recap then, your dad was basically using his free labour to do some cold calling which is obviously a big part of the SDR role. And then you went into 

Kaitlen Kelly: yeah, he was like more so. Yeah, he's I'm not buying you a designer bag at 15, but if you want to go sell some of these courses, here's a call list. I'm like, here we go.

Started dialing!

Will Koning: That's how you got to start, right? You got to get on the phones and just get talking. I imagine at 15, though, that must have been a little bit scary?

Kaitlen Kelly: This. You know what? In hindsight, I don't think it was. I think I had like my eye on the prize. I was paid like [00:04:00] 10 percent on each, it was a certification course that I was selling. And so I just broke down, worked backwards. How many do I need to sell to get this bag? I just called shamelessly. I don't even think I put too much thought into it, which is the blessing, right? When you go in with a little naive.

Will Koning: Yeah you know what, Kaitlen, I've known you a little while now, and it sounds like you've always had your eye on the prize. So I guess that's just part and parcel of who you are. Maybe you were just a born salesperson, eh?

Kaitlen Kelly: Yeah, maybe here we are.

Will Koning: Excellent. Looking back, what has sales as a career enabled you to do that you don't think you would have been able to do without it.

Kaitlen Kelly: I think, yeah. So when you ask that question, there's two things that come to mind to me. And I think the first thing is sales has been able to allow me to have a bigger impact on those around me outside of just my analyst role that I was in. So I think going through my experiences in my, kind of career transitions from something more typical and then [00:05:00] going from SDR to it moving across the pond to a country I've never even visited and all these different things that kind of add up.

It's given me the opportunity to share that expertise and experiences with others. And then I think one big thing that I wish I would have done is I just wish I would have taken that jump sooner. So it's given me a platform where I'm able to educate people on the opportunities and hopefully inspire them along the way, to go for it and not second guess themself and be a little bit more bullish about it.

Will Koning: Yeah, absolutely.

Kaitlen Kelly: And that kind of ties back. That's where I think the second thing it gave me is like that confidence. Cause it took, people believed in me before I believed in myself. And it was that repetition of doing it over and taking big risks that it ended up coming to fruition in the way that it has. So I think those are the two big things.

Will Koning: You talked about taking risks and taking the plunge, so to speak, I suppose it's easy to say, Oh, I just did it at the time. But what was it that finally pushed you to keep to go for it?[00:06:00] 

Kaitlen Kelly: To like the which one the first one when I transitioned from fashion to sales

Will Koning: Yeah, I think so, and then I guess maybe then tell us a bit about how you went from, sales to over here in the UK because it's quite a story. 

Kaitlen Kelly: Yes, of course so I think the thing that kind of pushed me from going from fashion and then switching over to sales was looking around and seeing the nine to five, the lifestyle and where people were at, where I may be at in five years from now. And then just reflecting a little bit and thinking, does that actually align with my values? Is that going to, is that inspiring to me? Is that where I want to be in the next five years? And is that actually going to help me hit my financial goals that I have? And so as I was doing the maths and looking around, I was like, there's, it's going to take me five to seven years to get over a hundred K. So it's is that something that I can do living in Seattle, which is an expensive market as well? I knew there was like more bite that I had, more to [00:07:00] give. And so that was the first thing. And I was like, terrified of it because you invest all this time, you, all this money into your degree and you're sitting there and you're just, not silently, but slowly climbing that corporate ladder and trying to be patient, and then I was willing to scrap it all away, take the risk on this and I literally, I remember calling my dad, telling him I was going to do this. And he was like, no, you should just, you should be like more patient. Nordstrom's been so great. And I was like, look, give me six months. I'm going to bet on myself. I might be going back, but let's just see what this is all about. So I went in with the mindset I'm going to work my ass off because I can't fail. There will be a way forward from here. So it was just getting comfortable with that idea and accepting the change, leaning into it. And then one thing that I learned early on in my career, also in the fashion industry, all the way through, which is what pushed me forward and taking on these opportunities, which would be the one of moving out to the UK is you [00:08:00] never pass up an opportunity, even if you want to run to where the fire is, right? That's where the most opportunity and growth is going to come from. So if you run towards the most ugliest, scariest thing, something's going to come out on the good side on the other side of it. So this is something that I was like, when things come to you and you get tapped on the shoulder for something that maybe you didn't even think you were great for a student for, but somebody else sees it in you, you just go for it, and you trust that they're going to help guide and build you, but also trust that you have the resources within you to figure it out.

Will Koning: Yeah. But when you say that, I think about my journey and all the things that I didn't know, but I knew in my heart, this was the right thing to do, but just taking that leap forward, and even you don't know the answer, how it presents itself to you, you would never do that if you didn't take the risk.

Kaitlen Kelly: Yeah. I think that's, I think too, is like a lot of people want to know it all before they jump into it, and it's like, how do you get comfortable in that unfamiliar zone? And just trust that it's all going to, you're going to figure it out as you're going as [00:09:00] if you're like building the wings on the plane, right?

Will Koning: Absolutely. On that then how do you get comfortable being uncomfortable?

Kaitlen Kelly: Repetition, like forcing myself to do this because I have severe anxiety and it's to the point that it used to be like debilitating where I would turn down like, talking, like getting up and like sharing, I wouldn't speak up in classes. Like I was just so scared of it. And so I had to change my mindset and one of my biggest things is like fail fast to learn quicker. So I'm like, Oh, just go dive into it. Rip the bandaid off. The first time is going to be the worst. So we'll get better. But then the other thing is getting comfortable with the uncomfortable, right? So anytime something scares me or I'm afraid to do it, that is like a trigger for me to actually go and do it. And that's yeah, that's like a value within me that I have to hold myself accountable to. So if I'm nervous about something that I'm like, I have to volunteer for this, and I think the way that I built [00:10:00] this muscle over time was I did this throughout my entire, like I did this in professional and personal life. So when I made this switch over and I was like, okay, I need to keep pushing myself because I can see the rewards on the other end, every time I push myself outside my comfort zone. So then I started doing it where I was like, okay, I'm going to go skydiving. I'm terrified of fish. So I was like, I'm going to go get certified as a scuba diver. PADI certified. So I faced fish underwater.

Will Koning: Yeah.

Kaitlen Kelly: Yeah. So I was like, I just, and then you just get more comfortable being outside of that zone, and the more times that you do it, then you start to trust yourself that you'll figure it out along the way, and it builds the confidence.

Will Koning: Do you know, Kaitlen it's just it's just so striking you're talking about not being confident and being scared of this and having anxiety and nervous, but that's just not how you come across to me, certainly in my view of you, so to speak. Do you get that, do you get that comment a lot?[00:11:00] 

Kaitlen Kelly: I do get that comment a lot, but I think there's, I think as you're figuring out your career and going through life, like you find ways to make it work for you. I know that I have like anxiety and all these things and things are gonna make me nervous. I'm gonna probably over prepare for a lot of things. I'm going to do my research. I'm going to tap into different people, ask them about their experiences. Just so that I can brace myself for what may come, and so I think you find different ways to make it work for you, but the biggest thing is just doing it, going for it. And it is going to be bad sometimes, and it might be completely awkward. And I've had plenty of those situations, but you just move on with it. Everyone's human. So it's fine.

Will Koning: Yeah. No, I totally get that. What would you say are the biggest challenges about being a sales executive that, that you perhaps didn't know you were getting yourself into when you were coming in.

Kaitlen Kelly: I think one of the biggest challenges is going to be, I think I'll give two examples here because one of them that I think most people need to brace [00:12:00] themselves for is that You've got to come in and be resilient as hell. No one's going to hand you the perfect playbook and tell you exactly what to do.

People can guide you and give you the science behind it, but bring yourself as the art, so that you can find different ways to create that differentiated experience as you're prospecting, building relationships. So I think that thing is don't be afraid to show up as who you are.

And then the other thing, which is really interesting is everyone says "sales is a roller coaster." You're going to have the highs, you're going to have the lows, and you may get into a company that is super hot and you could have a super incredible career for the first six to eight months and, or a year, however long it is. And then you may transition to another role and kind of have a little bit of a lull and that doesn't, a lot of what I see happen sometimes is sometimes people will second guess themselves and start to wobble a little bit. And so my advice on this is just understanding that like, it's not always going to be on the highs, and when you do hit that lows, like rather than looking to your success directly related to what your [00:13:00] attainment or the number is, try to look at it as building or collecting tools for your tool belt. So in every different experience, how are you collecting different things that are going to help you for what could come next, rather than just looking at what that attainment is, and I'll give you a more qualitative perspective of it as well.

Will Koning: Yeah. Amazing. 

Will Koning: What's been like the best thing? If you have to [00:14:00] choose one thing, whether it was like one experience what is like the best thing you've ever experienced as a sales professional?

Kaitlen Kelly: Ithink the best experience gosh, that is such a difficult one because there's been so many different things. But if I have to wrap it into 1 whole collective thing, I think the best experience is the exposure you get of talking to so many different types of people. So then that actually helps build confidence as a person, but you're building so many different friendships in your network and stuff, and you're learning so many different industries, roles, tools, and so it's just insane how quickly you learn within a sales role and how much of an expert you can come in so many different areas, without even knowing that it's happening. You can just reflect back and be like, oh yeah, I worked in MarTech or I worked in the sales engagement platform. Yeah, I was a BDR and I'm an account executive. There's just so many different ways that you can go once you get into that sales role, because you have exposure to all these different things and it's different every day.

Will Koning: Yeah. It's so funny. But all those like different things like you, [00:15:00] you've mentioned learning, you've mentioned meeting people, you've mentioned all these new different challenges, but you haven't mentioned the money side of it, right? We live and die by the numbers in sales. Where does that come in?

Kaitlen Kelly: You're so right. What is happening over here? I haven't mentioned the money once. That is, yeah, that was one of my drivers, right? Let me get out of fashion and into sales cause I'm trying to make some cash. But yeah, I think that's the thing that is missed. People don't understand the type of career and lifestyle you can have and how lucrative it could be. It is challenging, but there's reward on the other side of the challenges. So if it's something you're willing to commit to and invest in that learning and development and kind of be a student of sales, then sky's the limit. And I think that is exciting because there's no cap for you.

Will Koning: I love it. I also have to say I am not necessarily the most financially motivated salesperson myself. Hence why maybe I built a sales training school. So two more questions then is. One, what's your favourite quote, and [00:16:00] why? 

Kaitlen Kelly: This is so good. I was prepped on this one that I was going to have to come forward with this. And it's it's really hard to choose one. I think I'm like one of those people that is like, Oh, I don't want to be cornered into answering one thing, but I will go for one. I think for me, my favorite quote, and I say it all the time and I just absolutely love it and it probably stems from my competitive edge. But it's, "If you're not first, you're last." And I just love that quote because it's yeah, if you're not first, then you're last. What can you do to get better? And how do you get to that next spot? And I think that's, that quote just always keeps me going and it tells me like, I still have more to do. So I think it's from I don't even know the name of the movie, it's like a, what's the guy's name? Ricky Bobby or something,

Will Koning: Oh, from Talladega Nights. 

Kaitlen Kelly: Yeah. And I just love it. "If you're not first, you're last." I'm like. He's not wrong. So we got work to do.

Will Koning: I'm just thinking about all the outtakes on that movie at the end. Some of them are so funny. 

Kaitlen Kelly: Yes, exactly.

Will Koning: Yeah, very good. The [00:17:00] final question from me really, Kaitlen, is you know, picture yourself, that person that was so nervous about going into sales and you weren't sure, and it was in that time of do I, don't I, what are the three pieces of advice you would give that person to you now you are further along in your career? 

Kaitlen Kelly: I think if somebody is trying to make the decision of if they do it or don't do it, the first piece of advice would be like, write down what would happen if you don't do it? What's the risk? What are you going to miss out on basically? And kind of put that in front of yourself, because there's, you're probably going to have a very small list of what you're going to miss out on or what you're going to lose. So I put perspective into it of like, why not go for it? The second piece of advice is reach out to people who are in that role, have some conversations with them, see what resources are available for you to get familiar with what that day to day may be, kind of what does that experience look like? Look at people's career trajectory from that role where they may be now. So that's two big pieces of advice, and then I think the third one, which is just [00:18:00] like more personal, but some advice I got from someone, and this is like you're the one that gets to charter your own career. You get to decide what that looks like. And there's no perfect path or straight line. So you got to bet on yourself and trust that you will figure it out along the way. There's going to be people supporting you and there's so many resources to tap into that if it's something that you're even curious about, you might as well scratch the surface and give it a shot and see where you land. Right, as we go back to your first thing, you write 

Will Koning: down the risk, what have you really got to lose? And I think in the startup world, we say, the biggest risk is not taking any risk at all. And then you do, you talk to others, like you say, you speak to your advisors, your mentors, your friends, we talk about stuff, you talk to me about stuff, that happens, and then the third thing is, what was the third one again?

Kaitlen Kelly: The third one is bet on yourself. Like you're in charge of your own career progression and your path, and it can go in any direction, so you might as well, yeah, trust, trust what you want and go for it. Don't hesitate.

Will Koning: Exactly. Yeah, and it's all makes sense, write it down, take some risks, speak to others, [00:19:00] then ultimately, it's your choice to make, right? And that's it. Amazing. That's very good advice, and for anyone listening Kaitlen really has had a very successful career. If you go and follow her on LinkedIn or anything else like that, you see what she's done. She's worked in some of the most, exciting UK startups. I know she's about to go on another adventure really soon, which is really exciting to watch and see. Kaitlen this is now your time to do some shameless stuff for promotion. We are salespeople after all. What do you want to say to the world? And yeah, it's your turn now.

Kaitlen Kelly: Amazing. Yeah. Thanks for the spotlight. I was waiting for my five minutes, just kidding. I started out as an SDR. Now I'm in sales leadership and my biggest passion is developing and scaling top performing sales team, and I've had the opportunity to do this at two incredible companies previously, so Outreach.io and Klaviyo, and I'm getting ready to take the leap over to Multiverse, which is in the EdTech space as well, so definitely aligned with my passion on making sure that people have equitable access to some of these resources. [00:20:00] I think outside of that is it's just, if you want to get in touch with me, I teach courses through Sales Impact Academy, I have one on one coaching sessions through mysalescoach.com, and then of course, LinkedIn is a great resource as well. And I'm always a resource for chatting.

Will Koning: Absolutely.  And yeah, I'm sure there'll be some more announcements about your next part of your journey real soon.

Kaitlen Kelly: I am looking forward to it. Thanks so much for having me on. I appreciate it. This was a blast.

Will Koning: All right. Thank you everyone. See you in the next episode. [00:21:00]