Cultivating a Creative Brand Strategy | Alaina Caldwell, StyleWorks Creative

The Brand Licensing Podcast

March 1, 2021

Ready for a new episode of The Brand Licensing Podcast? Tune in next week to hear the latest and greatest on creative strategy with Alaina Caldwell from StyleWorks Creative.

After graduating from Rutgers University in 2004 with a Bachelor’s Degree in Fine Arts, Alaina began her full-time career at Frederick & Froberg, where her design ability and drive made her an instant success. She developed a passion for licensing and brand extension that when coupled with her entrepreneurial spirit led to the foundation of StyleWorks Creative. Able to move seamlessly from project to project, she enjoys branding for children in particular, perhaps because she has two lovable kids at home.

Alaina’s work ethic extends into her free time as well. A former NFL cheerleader, she never shies away from a physical challenge, participating in such events as the Tough Mudder and the Susan G. Komen 60-mile walk for breast cancer.

As a cofounder of StyleWorks, Alaina is responsible for creative direction, design development, and project management, as well as managing internal and freelance staff. Her style guides and visual presentations have driven numerous retail campaigns, domestic and international.

Tune in below to hear the full episode, or check us out on Apple Podcasts or Spotify. Don’t forget to subscribe!

This episode is brought to you by Brainbase. Learn more here:

Episode Transcription

Emily Randles: Hi Alaina! Thanks for joining us today on the Brand Licensing Podcast.

Alaina Caldwell: Thanks for having me. This is my first podcast, so I’m super excited.

ER: Great! Well, for our listeners, Alaina is a Partner and Creative Director with StyleWorks Creative. And today, we’re discussing with her how brands should be thinking about their strategy and how that translates into design work and even brand extension opportunities. But before we get into that, can you give us a quick rundown on your resume?

AC: Sure. Well, I went to Mason Gross School of the Arts at Rutgers University, and my major in school was actually painting. But pretty quickly I realized that I was more interested in the business side of the arts and I was also super afraid of becoming like a starving artist. So I went out and I found an internship at a creative agency in Montclair, New Jersey called Frederick & Froberg Design Offices, where eventually I started my full-time career. It was also there that I was introduced to the licensing industry for the first time and I just was hooked. I still live in New Jersey, but now I’m a bit closer to Philly. In 2012, Tom Froberg and I started StyleWorks Creative to focus a bit more on brand development strategy and the creation of licensing style guides and packaging, especially for the entertainment, lifestyle and consumer product industry. We’ve been really fortunate over the years. We’ve had amazing clients: Discovery, Viacom, CBS, NFL, Pepsi, and so many. It’s been awesome.

ER: Yeah. Those are great brands to work with.

AC: Thanks. Yeah, it’s been fun.

ER: Well, we can’t wait to kind of hear more about your expertise and dive in. You noted your partner, Tom. And we spoke with him previously on the importance of style guides and having strong creative direction for one’s program. But for the purposes for our listeners today, we’re really going to talk about strategy and how that’s a critical step in brand extensions and the creative process. So we’ll just jump right in here. As a creative agency, can you tell us how your team approaches strategy for clients and what’s included in that strategy?

AC: Sure. So when it comes to strategy, we always try and see what the brand owner or a licensing agent has gathered or determined first. As a creative agency, there’s a lot of times that we’re pretty much a visual extension and a companion to bring an agent’s strategic vision and idea to life. And in these cases, again, we sort of partner with them, lending them our experience and design expertise, but ultimately keeping their selling strategy at the forefront. But then there’s other times where, especially with new brands to licensing, we work with the brand owner to create the strategy for the brand. In these cases, we have a process that we define the brand’s overall purpose for licensing. We define the target audience, the vision and the reach for future brand extensions. We look at the overall essence of the brand, the brand’s personality and attributes, and ultimately all of this research puts together a product strategy.

ER: Off the top of your head, do you have any examples come to mind of how this worked really?

AC: We actually worked on a project for a brand called THC. They were entering into the cannabis space and they wanted to create… they own and they wanted to create this brand that was creating cannabis-related products. And it was really starting from scratch. It was a brand. They did have some roots in the nineties, but they needed more of a story of today. And it was really a great process. Actually, you can check out our website, we have a little bit more about the process there, but defining this audience. And it was kind of defining many different audiences of these different cannabis users and things, which it was a process for sure. But, you know, I learned a lot. It was great.

ER: Yeah. I like what you said about telling the story and, and keeping that going. And I’m sure with different consumers, different consumer types, I guess I should say, using the product differently – you have to tell that story in different ways.

What value does the strategic approach… how can that help brands differentiate themselves in the marketplace?

AC: You know, a lot of times people just are like, yeah, let’s create some art. Or they think, like somebody says, hey, you need a style guide and they have all this beautiful art that’s created that in the end, nobody really uses. And it’s such a shame. And you know, we’ve kind of been on the end of that, where we’ve been hired to do a style guide. And then all of a sudden it’s like, oh, we only did watches. And it was like, oh, okay. So it’s like the art that was created doesn’t really use. So you can create a ton of cool designs, but in the end, if the products your audience really needs are more hard goods-focused, you won’t be using them. So by going through that strategic process and defining the product strategy before the art is even created, you can create so much smarter of a deliverable and save a lot of money and time. You can also, by doing that diligent research, you can really figure out where you fit in the marketplace and how you can stand out amongst your competition.

ER: That really resonates. Can you say more too, about some of the, the hard goods and how maybe it’s not necessarily a t-shirt design, but it’s products how that works.

AC: Totally. Sometimes, you hate to do a logo slap because it becomes sort of promotional looking. But there’s a lot of products that it’s more about the color of the product, the texture, the materials that are used that are speaking to, say, it’s a vehicle line. It’s matching the colors of the cars or something like that. So you’re not necessarily putting these crazy graphics on everything. Cause that’s obviously not for every product. It’s about thinking about how much art needs to be created for whatever line you’re about to put out.

ER: Especially, and then just again, thinking through telling that story, too. So what’s the story of that car line or that product extension and how does it fit for the consumers?

AC: And then it seems more on brand because you’re showing the exact same color ways of the vehicles themselves. Or it doesn’t have to be this over the top   screaming logo. You can do it in other subtle ways.

ER: Yeah. And me, myself, I feel like lately, especially I’m an Instagram user. Looking at brands and things that are really resonating for me personally. It’s just like the less is more, but the subtlety where it just, it feels like this is their brand. And I want it because of that, even though it may not have their logo flashed over the top of it, maybe it’s even just the packaging. How does the strategy look for an up-and-coming brand versus a brand maybe looking just for a refresh?

AC: I think for up-and-coming brands, it’s good to focus on that core audience. And really look at the products that are easy sellers to the audience. This is your low hanging fruit. And it should be there for you to just pick up right away. This is your first things to hit the market. There should also be a major focus on other competitive brands and where they’re succeeding in the market. So you can see again where you live and how you can stand out. For more seasoned brands that are just looking for a refresh, I think it’s more about looking at where they’ve nailed it in the past and then figuring out new ways to build on that success. It’s also really important to look at what’s trending in the marketplace and how to get your brand to be as relevant as possible. And then sometimes it’s even about expanding your audience into a totally new market. I think a really great example of a brand doing that would be Crayola and their venture into Crayola beauty, which then becomes this amazing launch point for them to become more relevant in the adult space for future brand extensions.

ER: It’s interesting. I had someone recently reached out about Country Living, doing mattresses, and they were like, why is Country Living doing mattresses? And I was like, well, you know, just that in and of itself maybe doesn’t make sense. But maybe they have beds and bedroom furniture. And so this is a great next piece to further out in terms of a brand extension. But maybe that’s what their consumers are expecting because of their overall portfolio.To your point, kind of expanding the audience in the marketplace.

When completing a strategy for a brand, what are some things, I guess if you’re working with a new brand, what are some things that would signal a green light for them to be ready for licensing? Are you always thinking of licensing when you’re working on a strategy? How does that work?

AC: Usually we’re hired to think about licensing when working on a strategy. In the past, that’s been the majority of our experience unless it’s more of like marketing strategy. But you know, again, we’re kind of creating this checklist of the brand personality, the essence and everything. And once all of that strategy is put down on paper, then it’s really important for us to create this visual brand vision document. And the more visual presentation that we can create, which really showcases the brand’s mission and the current success and any potential product applications that could help partners and licensees imagine their products in collaboration with that brand. That piece is huge. Once you have that, I think you’re ready to hit the ground running.

ER: So how are people finding you guys? Or how are you connecting with those kind of seeking licensing but need that creative approach?

AC: It’s funny. It was always like a word of mouth thing. As you know, this industry, everybody knows everybody and everybody moves from one place to the next. I kind of love when people move, they’re like, oh, it’s my last day here. It’s like, yes! Because then usually they’ll take us someplace else, which is nice. But now a lot lately we have been meeting a lot of new people who are just Googling us and finding us online, which is great. So it’s nice to see the website working.

ER: It’s funny, we were on a call earlier today and they were talking about how with COVID for 2020, they were like, this was going to be the year of travel. And we were going to go talk to so many more potential clients and use all these grand plans. And then COVID happened. And he was like, it actually was a good thing because we were able to do so many more meetings via zoom. And I can talk to somebody in California and then later, you know, New York or vice versa, all in one day. I think COVID has shifted more people online and just Googling and finding what they’re looking for and kind of being creative because just behaviors in general for business have changed. So that’s awesome.

AC: Yeah. You’re so right. It’s funny. That was our plan. We were going to be traveling. We were going to be going to London and all these different shows, different things. And then it was like, oh, nope, that’s not happening. But right now we’re talking to three international brands. So it’s like, oh, okay. It didn’t seem to kind of happen anyway. So it’s nice to hear that’s happening with everybody.

ER: Besides brand licensing extensions, what are some other recommendations that maybe came out of your strategy work? Do you help through, it sounds like you are focused on licensing extensions when you guys kind of scope your work with clients. But are there other things that come out that help and add value to a brand?

AC: Most of the time it is licensing extensions, looking at these different exercises and creating this strategy. One of my favorite exercises is when we’re looking at the core brands mission and seeing if it’s relevant to the licensing industry. And many times it’s not. It’s especially the case like for a media brands, like you were saying, Country Living. Many times their mission is about watching something or viewing or providing content for consumers when it comes to the core of their network or their magazine. But licensing is about products and experiences. It’s the lifestyle. And it’s a pivot from watching something to actually living it. Many times, you have to create a completely new mission statement just for consumer products and for licensing. That is probably something that comes out of the strategy work that we do that I’m not sure if it comes out of everyone’s strategy work. But it should, because a lot of times it really helps create a more cohesive program, especially for a brand that does not have a lot of assets to begin with.

ER: Yeah. And we talk a lot about that with our clients and making sure it’s connecting with their mission. It does make a difference from a relationship standpoint, too. Like the licensee wants to feel a part of the bigger picture and the impact that a brand is having. So if you are connecting their strategy to their larger mission and purpose as a company and as a brand, I think that that helps obviously creates more authentic products for consumers and therefore more successful and just overall make a bigger impact. Before we go on, we’re going to take a quick pause to hear a word from our sponsor.

ER: Today’s episode is sponsored by Brainbase. Brainbase is a technology platform that helps brands manage and monetize their intellectual property. The current platform assist helps brands track their legal contracts, sales, royalties, creative and product approvals, files, analytics, and so much more. Additionally, they’re working on launching a new service, Marketplace. Marketplace will allow you to showcase your brand and discover new opportunities from a global network of prospective partners. We use Brainbase Assist program to manage and track licensing programs for our clients.We love the analytics and reporting tools and are excited about the new rule to reporting features they’re rolling out. Check it out if you’re looking for an online management tool for your program. We’ve linked to their site in our show notes. Now back to our show.

ER: What are some trends that you’re seeing today that you feel others should pay attention to?

AC: Right now within the last few months, especially we’re seeing a major focus on e-commerce and web-based product launches. This includes delivery services and boxes and things like that. Print on demand. And even this digital component or digital experience that’s added to the product itself or packaging.

ER: We’re seeing those same trends. I was even reading an article the other day in Bloomberg about the bland, which is these direct to consumer brands and that they’re offering unique product solutions to consumers, but in a very kind of regimented way that is working very well. So thank your Warby Parkers, and Your Way. But we also think that those brands are kind of right for extensions as well as they become more mainstream with consumers.

AC: Yeah. And technology is just incredible. The Warby Parker, that’s a great example. To be able to try on glasses without even being in the store is just tremendous.

ER: And even just the purchasing power of social and direct to consumer, I think retailers are doing a good job connecting there as well. But I think licensees and licensors need to have a collaborative approach when thinking about your online e-commerce strategy and working with your licensee and not just kind of flying solo.

Speaking of, I know we talked a little bit on COVID and how that’s changed our business. Are there any other insights or ways that COVID has changed the creative approach for you guys?

AC: COVID, you know, it’s crazy obviously for everyone and just in general for our agency, in the beginning, it was a little scary. How is this going to affect StyleWorks. But as the months go on, I’m really surprised and really happy about how resilient our team is. It’s funny. We’re super flexible in nature, just pretty much with everything. So that flexibility really was a huge asset in a time like this. In general, besides all of the zoom calls and everything else for the work that we do, we did find that the pandemic and the current cultural attitudes are shifting the graphic trends themselves in a major way monthly. So subscribing to WGSN, which we do and looking at trend forecasting, it’s like, you have to be on this stuff because these things are just changing almost weekly. It’s crazy. So for example, standard trends like decade trends, like eighties, nineties, they’re being replaced with more overwhelming optimism or a focus on empathy or more causal themes.

EC: Yep. I’m shaking my head. I know you can’t see me, but yes, that’s really interesting, too. As you pointed out, I feel like it is changing very rapidly. So I’m interested to see what 2021 brings us.

AC: Yes. Me too.

ER: Jumping into what  a brand wants to work on a strategy and more design, but they’re on a budget. What should they tackle first or where can they have the most impact?

AC: For a brand on a budget, I would recommend looking at the licensing strategy as more of a tiered approach. Think: are there any deals that we can do without major heavy lifting? For example, if you have some art assets, can you launch with a soft goods or print on demand program while you’re sort of working on this more ambitious, larger, hard goods line or experience that has more lead time, more manufacturing, more approvals? Can you sort of tier it so you’ve got some fast cash in the beginning and then sort of the longer play as far as the licensing strategy. Also, I had done a seminar or a webinar early in the pandemic called Marketing in the New Normal. In that, we had talked about are there ways, now that everybody’s on a budget, to get licensing deals done without spending money? And I think there are, it’s looking at all of the assets that you have so far. Are there vintage logos? Are there vintage assets that you can sort of dig out and dust off and use in a little vintage collection? Or is there something that you might have done a few years back that seems a little dated or you’ve done it before, but you can change the color, add photography. Or even a play on scale, like a really simple blow up of the character – huge. Those things are ways to kind of repurpose and reuse old art, but make new money.

ER: For sure. And just thinking about how that stuff looked when it was originally launched and what channels it was on versus the new channel. Even just getting stuff like that; that content out there more that consumers may not have seen, you know, 10, 20 years ago when it was first launched because it was in a couple commercials, versus on Facebook and Instagram and all the social media channels.

AC: One of our favorite stories to tell at Styleworks is we had done some really fun art for Harley Davidson bedding. It was like a very specific project for bedding. I don’t exactly remember the retailer that it was going to, but we created this art. And then I think it was about seven years later or maybe even longer. I was at Walmart and I’m in the register. And I see Snooki, probably the Jersey Shore, had her baby and on the cover of People magazine, it was like Snooki’s baby shower and it was a Harley Davidson rocking horse that was created by Kid Craft. And it was gorgeous. And it was using the art from this bedding exercise that we had done years and years in advance. But they had made some product and it was like, oh, well, that was nice. And it was kind of whatever. But it was years later, somebody went into the archives, they saw the art and they said, hey, this could be used for, you know… I would never think that that could be used on a rocking horse or like a baby toy. So it was so cool to kind of see it in action in a totally new light. And I think there’s a lot of really smart people in our industry that have that ability to do.

ER: That’s great insight and advice. People should be digging through their archives tomorrow.

AC: Actually, no. Don’t. Just cull it. They should come to you to refresh it. But, you know, honestly, we’ve actually even been hired in the past to dig through some of these archives and assess what is usable and what’s not. What is relevant and sort of like help cherry-pick certain graphics that can be repurposed. That’s been part of some of our style guide project.

ER: That actually makes a lot of sense. Again, if you’re not a design person, which I am not, I’m a visual person, but I’m not a design person. And so I can tell you what I like, but I think it takes an eye to say this is on trend, or you can take this and make it neat. Today’s trends, what’s going on today? And visually. And I think that that is great value, again from somebody that’s just a visual person. That’s kind of how I think. So I think that people should be considering that approach as well. Thinking of what brands, if they want to engage in strategy work, what is like a ballpark figure, maybe think like small, medium, large offerings?

AC: You know, it always depends with all the projects that we work on. It’s sort of the scalable approach. It depends on how many parts that you want to add. I’d say normally our budget for strategy usually starts around 10,000 and then it’s sort of like add-ons here and there. Some of our clients want a bit more consumer insight, consumer studies, more extensive research, and that can definitely add. But we really tailor every single deliverable, completely different for each brand that we work with.

ER: Okay. That’s helpful. You kind of piqued my interest when you’re talking about consumer research. Do you guys find it helpful to do concepts and test it with consumers to see, like, does this resonate or do you test packaging that way? Can you talk a little bit more about kind of ways which you can use consumer research?

AC: Sure. Sometimes we’ll conduct our own. Sometimes we’ll be a part of working with a brand as they’re conducting it on their end to give them sort of assets to test. One time in the past, we had worked with the Sprout Channel and the Sprout Network and they were doing some consumer testing. We showcased new packaging to a number of viewers from the network. And it was like, great insight. You want to cringe a little because you’re actually sitting there listening and you hear people picking up a fake package and they’re like, oh, there’s nothing in it. It’s really light. Things like that. I was like, oh boy. But you know, it’s really, really helpful as a creative agency to hear how people are interacting with your designs. It’s the same even for me working with a licensee specifically and hearing their needs. Because a lot of times we’ll be creating just sort of general packaging. That’s not answering their problems. So it’s so great to have that insight even from them on, no, we have to have this amount of violators on the package because there’s so many different call-outs and things like that. So that’s usually really helpful. Any kind of interaction with the outside world. And now I think it’s so much easier to gather an audience to test. Everybody’s got a mailing list. Everybody has these different people that they can tap for their opinion and people love to give their opinion.

ER: You had touched a little bit on helping licensees with packaging. Do you guys ever do strategy work for licensees? And if so, how does that work?

AC: We haven’t done as much strategy work for licensees since they’re more product-focused. I guess you can say creative strategy using our trend research capabilities. We’ve been contracted by licensees in the past for creative graphic development and product development direction really to help their internal team reinvigorate their product offering seasonally or a couple of times a year.

EC: Great. When thinking about design strategy and who this like works for, is there a market segment that this is more important for? Like children’s products and entertainment versus a CPG tech product that kind of tends to have a set logo and packaging that they don’t veer too far away from?

AC: In our industry, I really think brand strategy is important for everyone. Some brands are just really lucky and have an easier target market. And then it’s just a product late in market like children’s or entertainment brands. They might not have to do as much digging in the beginning to figure out the products to go after right away. I think it’s the more complex lifestyle brands that don’t have a lot of support of characters and visuals or this big hit entertainment piece behind them that they have to do a bit more creative work, a bit more strategy and more storytelling to show in their brand vision how these products and experiences can come to life.

ER: Yeah. That makes a lot of sense. Wrapping up here, what is something you’ve worked on recently that you’re really excited about or most proud about?

AC: It’s funny. I feel like every person at Styleworks would probably answer this question differently right now because we have a lot of really fun projects. But for me, we’ve been working a lot recently with IMG Licensing on the Jeep brand and actually a number of different brands with them. And for Jeep, the project started with more of a brand vision and then it expanded into a full global packaging and branding style guide. So that’s definitely a lot of fun. I love the brand. And we’ve also been doing a lot of products or projects with Crayola, which I personally wanted to work with Crayola for a really long time. So it’s always nice when that happens.

ER: Yeah. It must be so fun to think of products and then be able to bring them to life visually. Again, just not a gift that I have. So I think that that could be really fun, helping a brand kind of see where they can play and really bring it to life for them.

AC: It is. And you know, it’s funny, so many of our clients are repeat clients over the years and it brings me so much joy because, it’s like, oh, we’re doing something right, because they just keep coming back. But what happens after you have a client for so long, all of a sudden there’s a certain amount of trust where it’s that phone call of, hey, we’re pitching this person, we need XYZ. And like, there’s a certain amount of direction that’s given, but then it’s like, and what are your ideas? And, you know, you can sort of go crazy with the product ideas, which is a lot of fun in the last few years, the product development portion of what we do. It brings new energy and new excitement for me.

ER: Nice. It’s been great talking with you today. I know our audience has enjoyed your insights. If people want to find you online and connect, what’s the best way to do that?

AC: You can always take a look at our work and learn more about our agency at Also, I’d love to hear from you personally on LinkedIn, or you can even just check out some quick snapshots of what we’re up to on Instagram, @styleworkscreative.

ER: Well again, thank you so much for your time and for joining us today. And we look forward to connecting more.

AC: Thank you for having me.

IMC Licensing Logo Mark

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    The Brand Licensing Podcast

    July 23, 2020


Licensing is a relationship not merely between brands, but among people. At IMC, we build and nurture both of those relationships while delivering top-notch customer care that treats — and protects — your brand as if it were our own.

About Us

We’re committed to fostering dynamic brand alliances. Often those alliances are born from one brand’s need and another’s ability to meet that need. The IMC team are experts at recognizing and creating those opportunities, but our real expertise is people. Standing side by side, as consultants, partners, peers, and as friends, we’re driven by a singular purpose: creating a smart idea.