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Jen Rapp
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Liberty Mutual Spokesperson
And Doug, there's nowhere I wouldn't go to help someone customize and save on car insurance with Liberty Mutual. Even if it means sitting front row at a comedy show.
Greg Kilstrom
Hey everyone, check out this guy and his bird. What is this, your first date?
Liberty Mutual Spokesperson
Oh no. We help people customize and save on car insurance with Liberty Mutual together. We're married. Me to a human, him to a bird.
Jen Rapp
Yeah, the bird looks out of your league.
Liberty Mutual Spokesperson
Anyways, get a quote@libertymutual.com or with your local agent.
Jen Rapp
The agile brand.
Greg Kilstrom
Welcome to Season seven of the Agile Brand where we discuss the trends and topics marketing leaders need to know. Stay curious, stay agile and join the top enterprise brands and martech platforms and as we explore marketing technology, AI, E commerce and whatever's next for the Omnichannel customer experience. Together we'll discover what it takes to create an agile brand built for today and tomorrow and built for customers, employees and continued business growth. I'm your host Greg Kilstrom, advising Fortune 1000 brands on martech, AI and marketing operations. The Agile Brand podcast is brought to you by Tech Systems, an industry leader in full stack technology services, talent services and real world application. For more information, go to teksystems.com to make sure you always get the latest episodes, please hit subscribe on the app you listen to podcasts on and leave us a rating so others can find us as well. Now onto the show. With AI's ability to augment in house creative teams, how does that change the way organizations should approach both their creative strategies and how they evaluate the value of creative as a business function? Today we're joined by Jen Rapp, Chief Marketing Officer at Superside. Jen has had key roles at iconic brands like Patagonia, arc', Teryx, doordash, Owlet Baby and Klaviyo. Now she's leading Superside's rebrand with a focus on AI powered creative services that augment in house teams. Jen, welcome to the show.
Jen Rapp
Thank you.
Greg Kilstrom
Yeah, looking forward to talking about this with you. Definitely a topic top of mind for a lot of people. Before we dive in, why don't we get started with you telling us a little Bit more about your background and your current role at Superside.
Jen Rapp
Absolutely. So I kind of have an unconventional background for the traditional tech CMO these days. And I started my career as a rock climber back 20 years ago and got a job as a copywriter for a rock climbing company called Black Diamond Equipment. And I kind of worked my way through college as a copywriter, which was really like a real person's job in college. It's like, yeah, yeah. And then I ended up after that going to Patagonia, which was founded by the same man, Yvonne Chouinard, that founded Black Diamond Equipment. And I spent a decade at Patagonia. And that's pretty unusual for someone with a real, like their first real job to spend 10 years somewhere. But there was a reason I stayed for a decade and that's because I learned so much about storytelling and brand building and communications and how to take stories that, you know, maybe the public isn't necessarily ready for. Like back then at Patagonia, it was about environmentalism and using business as a force for good. That was all super new back then. That was not like the common place as it is today. But I, I spent 10 years there learning how to tell stories in a way that, you know, reflected the founder's vision but maybe the market wasn't ready for, and learning how to make them more commercial and learning how to tell those stories in a way that would appeal to our audience. And after Patagonia, I went to Tom's Shoes. Learned a little bit about like speed there and scale that, that Patagonia didn't have worked for Arc Teryx, a really well known outdoor apparel company. Very similar to, to Patagonia. And then I reached a juncture in my career where I was like, okay, I've got all these tech recruiters calling me for some reason, but I'm not tech. Like, my parents were tech. I'm from Silicon Valley. They were like, my dad was a NASA engineer, mom was an engineer. And I was like, tech is not cool. Like Patagonia is cool. So I had all these tech recruiters calling me. Or I could have gone on to like become the CMO of North Face or a brand that like really like was in my lane.
Greg Kilstrom
Yeah.
Jen Rapp
And decided to make the jump to technology. And my first big job in Technology was VP of marketing for DoorDash. At a time when Doordash was not known like it is today. This is pre pandemic stuff.
Greg Kilstrom
Yeah.
Jen Rapp
And that really taught me a ton about performance and performance marketing and data and analytics. And I was introduced to this whole new world of building a brand but under the microscope of today's marketing demands. And I've stayed in technology and technology marketing because I love it and because I love that it combines like left brain with right brain. And decided to take a role at Klaviyo. Klaviyo is marketing automation company. A lot of people compared us to like mailchimp when I joined, but got to take the company public. Like that is a marketer's dream and a communication person's dream is to like live that IPO and live that moment and again, really got to use a lot of the left brain in terms of like analytics and, and marketing as we built that brand and IPO'd. And now I'm here at Superside. And I'm here at Superside. We are, for those that don't know, like, Superside is a company that is basically built to be your creative teams. Creative team. Every creative team faces massive bandwidth challenges today. Anyone that's any of your listeners that runs a brand team probably manages a creative team as well. And they know that that creative team is always deeply underwater and they can be the blocker, they can be the bottleneck and Superside eliminates all of that. So our biggest customers are like the Google's metas intuits of the world that like technology companies that need to solve creative bandwidth issues. And so here I'm CMO very lucky to be and get to work with an incredible team of people that are helping to solve this like, very real marketing problem.
Greg Kilstrom
Yeah, wonderful. So, yeah, I think you might be the first CMO I've interviewed that started out as a rock climber. So I think that's, that's a dubious distinction here. So.
Jen Rapp
Yes, yes.
Greg Kilstrom
So yeah, let's, let's dive in here. And you know, as I mentioned at the, at the top of the show, you're leading Superside through a rebranding and with AI at the center. And so can you talk a little bit about the strategy behind the shift and how you're seeing AI augmenting that creative process?
Jen Rapp
Yeah, well, we as a business, much like every creative in the world today, realized there was a juncture between like embracing AI and using it for efficiency purposes, for innovation purposes. And we kind of as a company had to choose, like, are we embracing this or are we not? Are we staying on our path that's sort of AI free? And we decided to go all in, like all in on AI to bring the efficiencies and the speed and the creative Wonderment that can come when you truly embrace AI as a marketing team. And so we decided to up level and train our, all of our 500 creatives globally on AI so that they knew how to use the latest and greatest tools and programs. And we decided as a brand we were going to commit to like offering those efficiencies to our customers. And so our rebrand very much celebrates the use of AI, shows people how they can use AI and it really puts AI at the forefront of everything that we're doing. And so it was really a, was a moment of the company's history where it was like, all right, we can either like get on board or we could potentially be left behind. And I think a lot of marketing teams are feeling that same stress and pressure. And our hope is like, we can be everybody's creative team's shortcut through AI. Yeah, we can like in a flash bring your marketing team into the AI agent because we've done all the hard work, like it's a lot of effort to upskill your marketing team and your designers and your web UX people on how to use the latest and greatest AI tools. But we kind of did that legwork for you so that it can be an immediate transition for you.
Greg Kilstrom
So from a, from a market perception standpoint, certainly, you know, I talk with a lot of people, I've, I've talked with a lot of creatives that love the, the promise of AI and you know, while all of a sudden I get to do what I really want to do, which is be super creative but not do kind of the repetitive stuff and all that, there's certainly others that feel differently and maybe I'm an optimist when it comes to this stuff. So I try to look on the positive part of this. Others don't see it quite so positively. Let's be honest right now. How do you see that perception overall of AI powered creative services evolving over the next few years?
Jen Rapp
Yeah, we see that the same, we see the same thing. We see some of our biggest customers are a little AI hesitant and frankly we built it into our product so that you can literally click a button that says AI enabled or not and so that customers that may not be ready to embrace it have the easy opt out. And that's because of that market perception. And it's not just a perception, it's a legal issue. And there are companies that are very much concerned about future legal implications like of using imagery that's not copyrighted or using marketing assets that just simply cannot be copyrighted. Because you can't copyright AI. And so what we're seeing is a blend of marketers that some of them are still way over here kind of hindered back by their legal teams or regulations or regulatory concerns. And then there's others that are just like, you know what, the market is going to figure this out. Let's get on board and not be left behind. And it was really interesting. I was at a dinner of CMOs and creative leaders in London about a month and a half ago and our whole conversation was we brought us all together to talk about AI and marketing and creative and it immediately veered into that like legal concern, regulatory concern. And it was so cool. I think it was one of the big CMOs at the table basically spoke up and was like, hey guys, I get that we're on this like regulation topic and you know what, we could spend three hours worrying about it and getting nowhere. Why don't we stop talking about that and let's stop, start talking about the opportunity that AI brings to all of us as creative leaders. And that was such a cool moment to see, like, hey, we get this, we get there's concerns. But like, let's figure, let's focus on the positive like you said and let's focus on like the creative doors this opens and the efficiency gains that it can bring to all of our teams. Yeah, I think that's what we're seeing in the market like everywhere right now.
Greg Kilstrom
Yeah, yeah, agreed. I mean, I think, you know, those things need to get solved, but they're, I believe they're getting solved and stuff. But yeah, it's, it's really, there's, I think the gap between the leaders and the laggards is only going to widen over the next few years as far as being able to adopt this stuff. And you know, sometimes you kind of just have to trust the process of the, the, the regulatory, it's kind of, it's like with the whole cookie apocalypse and you know, third party and first part, you know, at the end of the day some of that didn't shake out exactly like the worst case scenarios. But I think it helped everyone to think about how they treated consumer data with respect and, and as good stewards of the data. So you know, no, no downsides, in other words, in doing this. But solely focusing on the, on the downside doesn't actually help anyone.
Jen Rapp
No, no. And frankly, like it's probably not going to be the creative leaders that are solving that problem. The, the, that's going to happen at probably the government and state regulation level and they're going to go fight it. Let Elon fight that.
Greg Kilstrom
Right, right.
Jen Rapp
And Sam Altman, you know, like, let's let them fight that battle and let's focus on like how we can further our craft with AI rather than worrying about the legal side. As marketers, we're not good at legal and regulations. We're good at creativity.
Greg Kilstrom
That's why there's lawyers, right? Yeah. Bingo. So yeah, I'd like to switch gears a little bit here and talk, you know, we talked a little bit about your diverse experience and wanted to talk about another aspect of that which is selling products versus selling services. And you know, you've worked with brands like Patagonia as we mentioned, also working with a service based company like Superside. How in your experience, how have the marketing approaches differed and you know, how do you look at the differences there?
Jen Rapp
It's funny, this might not be the answer that you or listeners would want to hear, but they're very similar.
Greg Kilstrom
Yeah.
Jen Rapp
And trying to take a different approach would actually be a mistake. Products, like whether it's a service or a concrete product, they exist to solve a problem. They exist to solve a customer's problem. So like a coat at Patagonia is solving the problem of keeping someone warm and dry. Doordash is solving the problem of getting food on someone's table. Superside, we solve the problem of creative bandwidth. And the way to sell a problem is through, through emotion. And I think B2B marketing and service marketing is really catching up to this and realizing, look, we're selling a solution to a problem. And what even if we're selling B2B, even if we're selling like, much like we are today, like the end consumer is still a person.
Greg Kilstrom
Yeah.
Jen Rapp
And they are still living with real life stresses. And we are selling something that solves that problem. And so I've always found whether it's Klaviyo or Doordash or Superside, where you're not selling like a tangible product that's in your hand, tapping into the emotion of, you know, your end consumer always wins. Yeah, same thing. Like it's a reason that like Patagonia and Arc' Teryx and outdoor brands and Nikes, like they sell an aspiration, it's aspirational marketing. Like we might be marketing a jacket and showing you a picture of a guy on the side of Everest and you're like, that's really cool. But it's the guy that's living in New York City that's actually going to buy that jacket. He's not climbing Everest. He's walking down the street. And it's very much the same thing. Like, no matter who you're speaking to, aspirational and emotional marketing always wins.
Greg Kilstrom
Yeah, and I guess that that's another aspect too, is that you've done, you know, B2C and you've done B2B in addition to product. And. And, you know, so I guess you touch on the. The aspirational piece. I think a big part of that can also be the storytelling component. And obviously, storytelling looks different if you're talking about Patagonia versus Klaviyo, but how do you look at storytelling? And, you know, in a. In marketing, a service like Superside, you can still.
Jen Rapp
Like, the beauty of Superside is like, we can still tell very visual and evocative stories through video, through case studies, through really showing the problems that we're solving for some of the world's best brands. So, like, we might create a product video at Patagonia that, like, shows a really cool sponsored climber going and doing something rad. Well, I'm gonna, at Superside, tell the story of one of the world's best marketers at Google who is drowning because they couldn't get all their performance marketing assets made and how we help them Sol problem. It's still aspirational marketing.
Greg Kilstrom
Yeah.
Jen Rapp
It's still telling a story. It's still telling, like a story of solving someone's problem. And again, I think, like, there's ways to do that across B2B and across services that still really resonates with the human being. You're still selling to that human being.
Greg Kilstrom
Yeah, yeah. So I want to talk about one last topic here, and that's creative as a business function. And this is something that you've talked about before. And I, having been, you know, I've managed creative teams, I've done that. Like, I've seen kind of the. Kind of it being misunderstood in business. And I think I'd love for you to talk a little bit about, you know, why is. Why is creative kind of treated differently in some cases, or maybe why are some people not thinking of it as. As the business function that it is?
Jen Rapp
I think because in the past, it was almost like an afterthought, and we were so focused on the strategy and the targeting and these new tools that were so incredibly helpful to marketers like Facebook, like LinkedIn, like new, like CTV linear and all these new tools. We got so focused on the how, we kind of lost focus on the what. Like the what you were putting in front of people. And now all of those tools are sort of table stakes. Everyone has access to Facebook. Everyone has access to all of the, like, how we're doing it. And we've been talking a lot with, like, CMOs across the world, and they're all saying, look, creative is the new targeting. It used to be like, the optimizing of the targeting. Like, the only way we really can sell a differentiated story today is through our creative. And holy cow, we're late to the game and we got to get the creative director a seat at the leadership table. And we're starting to see it shifting. And one concrete example of this that maybe your listeners would appreciate is over the last two weeks, my team really saw a dip in pipeline generation. We saw lower leads coming in, and we were all like, what is going on? So we dug in to every channel, to every issue, every targeting, every campaign, and one of our team members said, you guys, you know, we've been really busy with this rebrand, and we actually, like, haven't put out fresh creative on our paid channels in a while, Whereas normally we just have, like, this incredible hamster wheel of creative going out the door. You've probably seen our ads. They're hilarious, they're great. But we kind of put the brakes on that. And he was like, I think we're blowing it. Without a fresh creative, what'd we do? Created new ads within one day. We saw the performance coming back up with just fresh creative with, like, a renewed CTA like it that, like, ad fatigue is real and really strong creative is also very real. And I would just encourage your whole audience to, like, place an emphasis on creative. You know, just yesterday, me and the founder of Supersight were talking. He was like, jen, we're going to win this game on creative, not on our targeting strategies. Remember that in everything that you do. And it was like, such a good reminder that creative needs that seat at the table.
Greg Kilstrom
So, yeah, I mean, given. Given that and given, you know, everybody's being continually being asked to do more with less, and marketing leaders are certainly not strangers to those requests either. What role can marketing leaders play in ensuring that creativity is seen as, you know, as important as you're saying it is?
Jen Rapp
I think bring that narrative to the leadership team and actually show them, like, I think it's a show not tell exercise at times on behalf of the cmo like, to come to, whether it's the QBR or the weekly business review. Show the creative that is performing really well and show the creative that doesn't like, I think interjecting creative into the conversations is something that just hasn't happened. It will help the CMOS budget, it will help their ability to get more great creative made. Like, but it's kind of on us to, to raise that topic and show that as another almost like growth channel, creative as a growth channel rather than just like Facebook as a growth channel.
Greg Kilstrom
Yeah. So what about, you know, with, with AI being part of the equation now with, with creative, how do you see that influencing how creative output is evaluated, optimized? What does that look like?
Jen Rapp
Yeah, I think AI is a shortcut and like equivalent of efficiency. And every cmo, every marketer is being asked right now to be more efficient.
Greg Kilstrom
Yeah.
Jen Rapp
And I think really emphasizing that to your finance team, to like, to all of your stakeholders that like AI is our shortcut to efficiency. It allows us to do more with less. It's free or it's cheap. It allows us to iterate faster. And you know, the modern CMO, like about 20% of their budget is dedicated to like innovation. And AI is another way to focus on innovation and use some of that budget to upskill your team or bring in a partner like Superside so that you don't have to upskill your own team. That is a really great way to push forward your efficiency narrative.
Greg Kilstrom
Yeah. And in addition to that, I mean, are there, do you see AI enabling other things as well? Like know, enabling new kinds of creative work? I mean, you know, new, I don't know, new channels, new opportunities there. Like, where do you see some of the AI powered creative services that a company like Superside offers, you know, heading in the next, you know, few years?
Jen Rapp
It's a good question. Right now we're really seeing AI being used at the briefing and the ideation phase.
Greg Kilstrom
Yeah.
Jen Rapp
And that I, I'm seeing that even more than like new channels, I'm seeing that AI basically like compounds on human creativity and it allows your team to be more creative so that what is you're putting into the market performs better. And so our team is able to today like take small ideas that would have taken forever to storyboard or to craft scripts for and AI does it for you in a flash. Like you can literally prompt AI to create storyboards for you so that my team can bring six ideas for a video and put them in front of me. And as a marketing leader, I can look and say like, yes, no, yes, no, like way faster. And your team just ultimately becomes so much more efficient and thus creative with the use of AI. I also think it's going to do exactly what we all predict it can do. And that's like allow for faster iterating, more renditions of high performing creative. Just allowing you to go so much deeper into your testing and your iteration without like the need to tap into human capital. AI can do that for you.
Greg Kilstrom
Yeah, yeah. Love it. Well Jen, thanks so much for joining today. It's been great talking with you. I've got one last question before we wrap up here. Like to ask this to everybody. What do you do to stay agile in your role and how do you find a way to do it consistently?
Jen Rapp
Good question. I'm a mom of five. I have four dogs. I have a horse. The way I stay agile in my career is by getting outside and taking care of myself. Taking care like feeding myself in a way that keeps me healthy and allows me to continue to be creative. As a marketer, we manage people. It's our job to keep them motivated. To keep your team motivated, you have to stay motivated. So I very much like invest in myself and I do that in the outdoors.
Greg Kilstrom
Yeah. Love it. Well, thanks again. I'd like to thank Jen Rapp, CMO at Superside for joining the show. You can learn more about Jen and Superside by following the links in the show notes. Thanks again for listening to the Agile brand brought to you by Tech Systems. If you enjoyed the show, please take a minute to subscribe and leave us a rating so that others can find the show as well. You can access more episodes of the show@theagile brand.com that's theagile brand.com and contact me if you're interested in consulting or advisory services or are looking for a speaker for your next event, go to www.gregkillstrom.com that's G R E G K I H L S t r o m.com the Agile brand is produced by Missing Link, a Latina owned, strategy driven, creatively fueled production co op. From ideation to creation, they craft human connections through intelligent, engaging and informative content. Until next time, stay curious and stay agile.
Jen Rapp
The agile brand.
Liberty Mutual Spokesperson
And Doug. There's nowhere I wouldn't go to help someone customize and save on car insurance with Liberty Mutual. Even if it means sitting front row at a comedy show.
Greg Kilstrom
Hey everyone, check out this guy and his bird. What is this your first date?
Liberty Mutual Spokesperson
Oh no. We help people customize and save on car insurance with Liberty Mutual together. We're married. Me to a human, him to a bird.
Jen Rapp
Yeah, the bird looks out of your league.
Liberty Mutual Spokesperson
Anyways, get a quote@libertymutual.com or with your local agent.
Jen Rapp
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Title: AI and In-House Creative Teams with Jen Rapp, Superside
Date: March 17, 2025
Guest: Jen Rapp, Chief Marketing Officer at Superside
This episode dives deep into the evolving relationship between artificial intelligence (AI) and in-house creative teams, especially within the context of marketing leadership. Host Greg Kihlström welcomes Jen Rapp, CMO of Superside, to discuss how AI is not only transforming creative work but also the strategic approach brands should take toward creative as a core business function. Jen draws upon her unique career journey across top consumer and tech brands to frame the discussion, addressing both enthusiasm and hesitation around AI’s creative applications, and offering actionable insights on leveraging creativity for business value.
This episode explores the intersection of AI, creativity, and modern marketing leadership. Jen Rapp, with her breadth of experience, argues that creativity—now empowered by AI—is central to business growth and differentiation. Organizations are being challenged to rethink and elevate the role of creative teams, measure creative effectiveness rigorously, and adopt AI not as a replacement but an amplifier of human potential. The discussion underscores that while legal and regulatory concerns are real, leaders must focus on the transformational opportunities ahead—placing creative at the heart of marketing strategy for today’s agile brands.