EP31 - Storytelling for Success with Kayla Grey

In this episode of CMA Connect, the CEO of the CMA, Alison Simpson, welcomes Kayla Grey, sideline reporter for the Toronto Raptors, and host and co-executive producer of "The Shift with Kayla Grey" on TSN. Kayla will also host the 2024 CMA Awards Gala. Alison and Kayla discuss Kayla's career journey, the strategies that helped her build her brand, and how influential storytelling is in an industry lacking diversity.

00:00:00:00 - 00:00:23:16
Presenter
Welcome to CMA Connect, Canada's marketing podcast, where industry experts discuss how marketers must manage the tectonic shifts that will change how brands and businesses are built for tomorrow, while also delivering on today's business needs. With your host, CMA CEO Alison Simpson.

00:00:23:18 - 00:00:49:03
Alison
In today's episode, I'm thrilled to be joined by a very special guest. Kayla Grey is a trailblazing figure in the world of sports media. As the host and co-executive producer of The Shift with Kayla Grey on TSN, she's been at the forefront of driving important conversations at the intersection of sports and culture. Kayla is also a sideline reporter for the Toronto Raptors, bringing fans closer to the action and the many stories behind the game.

00:00:49:05 - 00:01:10:18
Alison
I'm excited to share that Kayla is also hosting this year's CMA Awards Gala on November 22nd. It's going to be a terrific evening celebrating the amazing creativity and impactful work of Canada's marketing profession and all that we've accomplished over the last year. As someone who embraces and has benefited from creativity is important role in building both brands and business,

00:01:10:23 - 00:01:37:17
Alison
Kayla will be a wonderful host. In today's episode, we're diving into Kayla's remarkable career journey, exploring some of the lessons she's learned along the way and her strategies behind building a powerful personal brand. We'll also discuss the critical role of creativity in marketing and storytelling, and explores Kayla's thoughts on the future of the sports and entertainment industry. Welcome, Kayla, I am absolutely thrilled to have you here today and looking forward to a great conversation.

00:01:37:19 - 00:01:39:13
Kayla
Thanks so much for having me. 

00:01:39:13 - 00:01:46:10
Alison
Now, I would love to start by having you share a bit about your career journey so far, particularly your experience launching The Shift on TSN.

00:01:46:13 - 00:02:12:19
Kayla
So I came to TSN as a radio producer. And sort of that was my intro into the sports world on a broadcasting space. So producing radio, Raptors game nights, Leaf game nights, and then really just working my way into getting in front of the camera, I noticed that there was not really anybody talking about the Raptors at that time, or the opponents that were coming in.

00:02:12:19 - 00:02:30:03
Kayla
So I kind of pitched myself to our digital team and said, hey, like, if you're a fan of the Raptors, I truly believe you're a fan of the NBA. Let me talk about it for free 99. And they did. And so that's how I was able to kind of build my rapport that way until I was auditioning for Sportscentre.

00:02:30:05 - 00:02:54:05
Kayla
I made my debut of course, and became the first black woman to host a sports highlight show in Canada. And so that was great for me to kind of really get my reps in that way, but then also get my intros in that way, too, with the national audience. I continued with my coverage of the Raptors and really, really knew that there was something I did want to also contribute to the network, which was a show.

00:02:54:07 - 00:03:15:22
Kayla
Roll around, 2020 comes around. We're talking about a lack of diversity within the space and one of my biggest things that I've championed all the entire time I was there was the lack of diversity in storytelling, particularly with marginalized communities, but also with women as well. And so, you know, I was thinking and mulling and I was just like, what do I want to watch?

00:03:16:04 - 00:03:40:20
Kayla
What does that perfect show look like for me? What are the topics? What are the conversations? What are the things aesthetically that I want to see? And I literally was jotting down every single idea on a napkin. And I brought it to our brand partnership team, who brought it, of course, to a sponsor. They came in and boom, we launched The Shift and we're, I think four seasons, and now still rolling strong.

00:03:40:22 - 00:04:01:07
Kayla
And yeah, I think like the first of its kind in this country in terms of it being a digital-based platform on a national network. And so I'm just so proud of the work that we've done. But I'm also proud that, you know, I was able to see a missing hole in the market fill it and it to be successful.

00:04:01:09 - 00:04:24:23
Alison
Huge congratulations. In your intro, you've shared two remarkable firsts, and I absolutely love the fact that you took charge. You saw an opportunity. You set a goal for yourself and you didn't wait for someone else to create the opportunity. You defined it, you pitched it and you were successful. So huge kudos to you. And it's easy to understand why you are as successful as you are.

00:04:24:23 - 00:04:27:10
Alison
And I can only imagine what the future will bring.

00:04:27:12 - 00:04:28:23
Kayla
Thank you.

00:04:29:00 - 00:04:51:01
Alison
So part of that is building a strong personal brand. And that's certainly critical for success today in the marketing profession, in the sports and entertainment profession. And I would say in professions in every single industry. So I would love you to share how you've approached brand building when it comes to your own brand. And what advice do you have for others based on your success and learnings along the way?

00:04:51:03 - 00:05:15:04
Kayla
Yeah, I think I've been very open about when I first came in because I was only at that time wanting to morph and mold myself into something that was way more malleable for an audience that wasn't used to seeing someone like me on their screen. And that backfired completely. It just totally took me out of my flow, how I usually talked, my spunk, my charisma.

00:05:15:06 - 00:05:52:08
Kayla
And I just remember there just being a turning point for me when my grandma called me and was like, you're not even sounding like yourself. Like, who am I watching on the screen? And me having to strip that all away because that was my protection at the time and just go into work bare. Not saying like bare naked, but I mean bare as in, like who I truly was, owning my culture, owning, you know, that I say things a certain way, that I debate topics a certain way, and understanding that in order for me to show up as the best version of myself, I had to come as myself, which took a lot of vulnerability.

00:05:52:10 - 00:06:11:19
Kayla
But it was to me something I think that helped to heighten me and my career. And also my platform was, people were getting someone that they felt were authentic. And, you know, to me, I was okay with people not liking who I was. And I was okay with people loving who I was. And you get a bit of both when you're, of course, in front of the camera.

00:06:12:00 - 00:06:34:19
Kayla
But it was a non-negotiable for me early on to change who I was or how I did things, the things that I cared about and the causes that I spoke up on. And I think when you think about branding, one of the things that makes you resonate with an audience is being very clear about who you are and your humanity, your ethos, what you believe in.

00:06:35:01 - 00:06:56:23
Kayla
And I think that that is the general theme and tie, because I can tell you, there's so many people that I've connected with on social media or at the arena or just, you know, out. And I don't think we would have conversations other than, you know, the fact that they say, recognize me or whatnot. Like, I just don't think that we would be in the same rooms as because of our upbringings, or lived experiences.

00:06:57:01 - 00:07:21:07
Kayla
But what I will say is it shocked me is no, but we have something to talk about because we share values. We share a love of sport. There's so many common threads that I think that people miss between themselves and other people that are so easy to tap into. So, you know, when I was thinking about what my brand looked like, I think the first thing that I said was, it has to be real.

00:07:21:09 - 00:07:45:22
Kayla
It has to feel good. It has to have integrity. And there was a very quick understanding that if all of those things were there, they would naturally come. An audience would come, my people would come, I would feel seen. And I think I've moved through different brand partnership deals, through different causes, initiatives that I've tried to take up, with the same kind of bar.

00:07:46:00 - 00:07:49:18
Kayla
And I think that's allowed me to sleep good at night.

00:07:49:20 - 00:08:10:21
Alison
That is such incredibly valuable learning. And the irony is you identified a missed opportunity. You identified the fact that there weren't diverse voices and pitched the network successfully on bringing a diverse voice. And then when you're in the seat, you try to conform. And I've been the first female a couple of times in my career.

00:08:10:21 - 00:08:11:11
Kayla
Right.

00:08:11:12 - 00:08:28:00
Alison
I fell victim to exactly the same thing. You get your seat at the table and then you try to conform instead of realizing this is going to be so much more powerful by not conforming and by stretching the perceptions and the expectations of the people around the table and ultimately the audiences you're trying to engage, so...

00:08:28:00 - 00:08:52:03
Kayla
Yeah, and to be clear, like for yourself, I'm sure you know this. It's not easy. That is not easy work. That is actually the hardest route available to you. But the rewards are just so amazing. And then I think you also know this, that table that we fight so hard to sit at is actually not even made for us to be sitting there at all, nor to be successful at.

00:08:52:05 - 00:09:14:20
Kayla
And so I think it's like out of necessity that we understand that, like we have to build new tables, we have to build new rooms, and that takes innovation, that takes awareness of self, that takes courage. And I think in order to succeed in any industry, courage has to be one of the things that you lean all the way into.

00:09:15:01 - 00:09:35:00
Alison
And especially in this day and age, and you're a very public figure. People's BS meter, it has never been higher. So yeah, not being true to who we really are, people are going to legitimately call BS on us. They're going to disengage. We're not going to be credible. And when you embrace who you are, it has such an incredible impact.

00:09:35:00 - 00:09:37:10
Alison
I also love the fact that your grandmother called you on it.

00:09:37:12 - 00:09:59:09
Kayla
Yeah, my my grandmother was like, absolutely not. We're not representing the family this way. And it wasn't that I was doing a bad job. I think she just, she just knows me so well and she I think she also just knows, like, I cannot let you have 20 years in this industry doing this. And then at the end when you look back at your career being like, man, like I who was I, I was like a shell of myself.

00:09:59:11 - 00:10:23:19
Kayla
And, you know, I'm very blessed that I, you know, it's it's a blessing and a curse. I came into the industry like, very young, like I was 19 when I first started interning with the Argos, 24 when I made my debut on Sportscentre. And 31 now. So, you know, as much as I was introduced to an audience, I was a completely different person back then.

00:10:23:19 - 00:10:48:21
Kayla
I didn't have my son back then. Like I grew with an audience. And, you know, when you're someone that is growing and aging and maturing on a personal standpoint, that also takes form professionally, too. And so I had to get really comfortable with like, hey, I'm okay to change my mind on things. I'm okay to stand a little bit differently in my 30s than I did in my 20s.

00:10:48:21 - 00:11:01:05
Kayla
And, you know, I think it's kind of this beautiful relationship that I've built with audience that they've kind of, in many ways seen me grow up and grow through phases. And that's been really special as well.

00:11:01:06 - 00:11:12:17
Alison
Yeah. That's amazing. Well, you're also, your audience is growing with you and a huge benefit you're bringing to TSN is that younger audience and those voices that they haven't represented before.

00:11:12:19 - 00:11:30:07
Kayla
Yeah. And I think that that was something that I really took on knowing that I might appeal to a different audience, but then also having the wherewithal and mindset, because at the end of the day, like it is a business, that this is going to be the audience that is going to be in the driver's seat when it comes to spending.

00:11:30:09 - 00:11:57:07
Kayla
I know how I spend, I know how the economy affects my age group or me. And so, you know, when I come to the table of ideation for The Shift, I can drive those conversations with my lived experiences, and what I'm seeing, what I care about. And I think, you know, because TSN was started so long ago and had a different group of audiences, those values and things are a lot different.

00:11:57:09 - 00:12:20:12
Kayla
I'm not saying that they don't matter. They still do matter. And, you know, when we think about a lot of the spending that still comes from that group. But I think as we're thinking about ways to integrate the new audience or the next generation, it is important to have that healthy balance. And so I add value that way of kind of being in the know, of like, okay, this is where we are going, this is the direction where we're going.

00:12:20:14 - 00:12:48:08
Kayla
But I still take a lot from the older generation because there was just a level of integrity involved in the journalism. And that's what I grew up on was, you know, the, the strength of journalism, proper question asking. And I'll be honest, I think that that's kind of what's missing right now, with this influx of information. And so, you know, I think that every generation leaves behind a beautiful blueprint.

00:12:48:10 - 00:12:58:20
Kayla
And we're doing the industry a misservice to not go back and reference, said blueprint. I'm not saying copy it, but to learn from it and to innovate that way.

00:12:58:22 - 00:13:10:19
Alison
So looking forward, building on that, looking forward. How do you see the future of sports and entertainment evolving, especially from a storytelling and an audience engagement perspective? And then I want to hear what excites you most.

00:13:10:21 - 00:13:33:05
Kayla
Yeah, and that's a great way to ask it, is what excites me, because I think in this world where there's so much change, the first thing that comes up is what scares us. And I think, you know, as you know, with budgets and all of the things, that fear stops us from trying new things or leaning into new directions in ways, and that's not going to be helpful.

00:13:33:10 - 00:13:55:20
Kayla
I think what excites me is all these different platforms that are coming in and new ways of accessibility. That was the biggest thing for me coming up is, I was not able to see myself on camera and I had to, like, illegally stream ESPN feeds just to see like black women in that space and that boils down to accessibility.

00:13:56:01 - 00:14:20:22
Kayla
So imagine now a younger audience, varying in gender, varying and sex, varying in beliefs, now has this like level of accessibility to seeing their stories being told. I think that that's what's exciting is now you can kind of reach people everywhere. I think where we're going is we're having that, but then now we're also seeing these streaming companies coming in.

00:14:21:03 - 00:14:52:16
Kayla
Right? And that is something to be mindful of. But when we kind of really dissect from like an entertainment landscape of, okay, well, when we think about like the Netflixes of the world, the Amazons of the world, it's this vast library of content, but there's actually no meter of like what's deemed successful. You might be watching Gilmore Girls, I might be watching The Wire and those numbers can't compete with each other because they're completely different.

00:14:52:18 - 00:15:23:17
Kayla
And so I think that that's the challenge, is figuring out the new bar of what is successful, what is that return of investment when we're talking about ideating and creating all of this content? And I think that's something the entire industry is shifting and trying to figure out right now is, is it truly quality over quantity, or are we going to revert back to the quantity model from in the past, where, you know, you had your TV, 28 channels, you got what you got.

00:15:23:17 - 00:15:50:02
Kayla
Right? And so I think that we're in that kind of question mark, of where we're leaning. But again, I think what excites me is now we get to answer that for ourselves. And now audiences get to answer that for ourselves. I've never seen an era in which an audience can sway a network to hire people, fire people, change content, switch up how content is being shown.

00:15:50:04 - 00:16:04:19
Kayla
It truly is this equal transaction and exchange between property and audience and I think in some ways that's going to help build a more collaborative front when it comes to the stories that we're telling.

00:16:04:21 - 00:16:17:14
Alison
Great insights, and you're absolutely right that we have so many choices today and we're all really, really busy. So you do get overwhelmed by too much choice and you do want a curated option.

00:16:17:14 - 00:16:17:22
Kayla
Yes.

00:16:17:22 - 00:16:24:03
Alison
Where we go to like friends and family and apps to, to shorten the list.

00:16:24:05 - 00:16:42:06
Kayla
You know, and they barely do. There's certain apps you go and it says top ten picks for you. And then it's because you watched this, another top ten picks. And because your mom watched this, here's ten picks. And it's just like, I think people just want something a little bit more custom.

00:16:42:08 - 00:16:44:12
Alison
Like, yeah, it's definitely a work in progress.

00:16:44:12 - 00:16:45:14
Kayla
Yes.

00:16:45:16 - 00:16:56:12
Alison
So I'm going to switch gears a little bit. We are so looking forward to having you host the upcoming CMA Awards, and I would love to hear, what are you looking forward to about hosting and what do you hope to take away from the experience?

00:16:56:14 - 00:17:27:21
Kayla
I think to me, storytelling is my purpose. Sharing stories, inviting vulnerability in people so they can find the confidence in that space as well is like my passion. And, you know, I think when people think about marketing and that realm, selling is the first thing that comes to mind. And to me it's seeing. Seeing is the first thing that comes to mind when it comes to marketing is, it's this like extension of saying to audience, I see you and this is for you.

00:17:27:23 - 00:18:02:11
Kayla
And so to me, I'm really, really excited to be in a room full of people that can activate that feeling of being seen and just also see the unique ways of their storytelling, the unique ways of which they've been able to reach people, to allow people to feel in short and long segments. I think that we don't give people enough credit, when it comes to being able to touch people and different mediums and means, and so to just sort of be in that space, I'm really looking forward to it.

00:18:02:13 - 00:18:14:02
Alison
I've had the pleasure of judging some of the awards. We've had more award entries this year than ever before, and ticket sales are on fire. So...

00:18:14:02 - 00:18:19:18
Kayla
I love that. I love that! Like, you know what? People really want to be amongst each other these days.

00:18:19:20 - 00:18:39:17
Alison
Absolutely. And you're going to be wowed by the caliber of the creativity, the diversity of thought and ways that the Canadian marketing profession has really delivered on very different business needs in a way that is so incredibly compelling for the Canadians they're trying to attract and actually have grown the business too. So it's going to be a very fun evening.

00:18:39:17 - 00:18:40:12
Alison
I'm looking forward to sharing it with you.

00:18:40:13 - 00:18:41:13
Kayla
Yeah.

00:18:41:15 - 00:18:52:17
Alison
Now, the awards very much recognize the critical role of creativity in marketing and business. How do you view the importance of creativity in your work, and where do you see it having the biggest impact today?

00:18:52:19 - 00:19:11:00
Kayla
Yeah, I think you always have to be innovating. You always have to go back to the mind of your six year old. And I think so much of us, when we grow up, we almost like negate that. But I think about my six year old son and, you know, I give him something to think about or he has Lego to play with.

00:19:11:00 - 00:19:39:14
Kayla
And we're both big Lego buffs. So I build by the instructions. Levi, my son, builds by his imagination. And I'm constantly learning from him when it comes to that, because you need a couple of things. You need space to do so. You need resources, of course, but you also need nobody telling you no, or nobody handing you the instruction manual.

00:19:39:16 - 00:20:07:05
Kayla
And I think I always go back to that when I'm ideating and when I'm thinking things and when I'm going through, what do I want to see? And what I'm realizing in this process is I'm not dreaming big enough. I'm not creating wildly enough because I have this mental instruction manual in my brain. And, you know, when I think about the most successful campaigns and most successful shows, those are people that were thinking well outside of the box.

00:20:07:05 - 00:20:34:16
Kayla
Right. And and so when I think about creativity in business, you know, as much as I'm also getting caught up to that because I was more in the creative space, and numbers were never my thing, I also realized how much the two go hand in hand. And so, you know, when I think about business and success and what made The Shift sell and what's still bringing in attention, it's the risk taking.

00:20:34:18 - 00:20:50:18
Kayla
And, you know, the reward at the end is what sustains us. But, you know, obviously you have to be mindful and work within your means. But I think that you're doing the project and the passion a disservice if you're not allowing yourself to kind of run wild sometimes.

00:20:50:20 - 00:20:54:10
Alison
That is such great learning. I love that you're learning from Levi as well, because your...

00:20:54:12 - 00:21:14:19
Kayla
Your kids are going to be your biggest teachers. As much as we as parents think that we're going to be teaching them, there's so many,  I, you know, I remember as a woman coming into the industry and being pregnant and thinking my, my career is over. Like, woman, pregnant in sports, about to have a kid, like it is done for me.

00:21:14:21 - 00:21:30:11
Kayla
And when I made my debut, I was eight and a half months pregnant. And I'll tell you, I don't think I would be as successful as I am today without my kid. Like, it just teaches you so much, you know?

00:21:30:13 - 00:21:32:17
Alison
Yeah, they get you to see the world differently.

00:21:32:18 - 00:21:35:19
Kayla
Different. Yeah, absolutely.

00:21:35:20 - 00:21:36:21
Alison
And

00:21:36:21 - 00:21:51:22
Kayla
It doesn't have to be kids. It could be your dog. It could be your goldfish. It could be, you know, a loved one. I just think, for me, it was having that extra body in my life, that really allowed me to take just everything to the next level within my career.

00:21:51:23 - 00:21:59:08
Alison
So to wrap up our discussion, I would love to have you share one piece of advice for our listeners on how they can grow their career. 

00:21:59:10 - 00:22:21:14
Kayla
Ooohhh. That's good. I think, so many of us get so caught up in the busy, so caught up in the busy, and so there's a two part. One, live Your life. And I'm not saying that because, you know, I think, I think you should go out and have fun. I absolutely do. But life gives you context.

00:22:21:16 - 00:22:48:21
Kayla
And so when you're at the tables and ideas are coming, you have lived enough life to understand what actually makes sense, what actually feels good, what do you actually like? Life gives you the greatest context, I think, for any decision that you make within this space. The second piece of advice is get back to your why. And if you don't have your why, take time to define it and don't define it

00:22:48:21 - 00:23:20:07
Kayla
so specifically. I would say that again, my purpose, my why, is to invite people to get vulnerable so they can then be confident, and that confidence is then going to invite other people to step into that vulnerability. I guess broadly I can say storyteller, but storytelling for me appears in so many different ways. So when you figure out your why in a broad term, it gives you permission to play and it gives you permission to apply that

00:23:20:07 - 00:23:53:09
Kayla
why in so many different spaces. I think what's what's so beautiful about life is it doesn't have to be this one straight path. The job doesn't have to be the job for the next 30 years. It can take many iterations and it can take many different versions. So I think in terms of career, really getting clear about the why, and the purpose can really help be the best compass for you, for next steps, for advancing, for, you know, switching things up, for transitioning.

00:23:53:09 - 00:23:59:03
Kayla
I think getting very clear about that, can be incredibly helpful.

00:23:59:05 - 00:24:04:17
Alison
I love your why. It is incredibly inspiring. And will take you so many places in your career.

00:24:04:19 - 00:24:06:20
Kayla
Thank you, I appreciate that.

00:24:06:22 - 00:24:15:08
Alison
Kayla, I am very much looking forward to sharing the stage with you. Thanks for such a fun conversation and looking forward to continuing it in person.

00:24:15:10 - 00:24:26:08
Kayla
Thank you so much for having me, and I cannot wait for these awards. I'm so, so, so excited!

00:24:26:10 - 00:24:38:23
Presenter
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