How can you expand your brand with digital marketing?

What has caused well-known brands to fall out of favor with their target customers?

How can you use digital to accelerate marketing feedback and adapt to your customers?

David Cunningham, President of Brand Partnerships at MySureFit, is a 20-year veteran of some of the biggest names in the apparel industry. He shares lessons and case studies from brands like Ralph Lauren, Nautica, and Burberry. His expertise in both B2B and B2C digital channels will set you up for success in digital marketing and digital customer experience.

Listen in to learn more, and find out how you can start making marketing changes within 48 hours.


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Voiceover: This is Performance Delivered. Insider secrets for digital marketing success with Steffen Horst and Dave Antil.

Steffen Horst: Welcome to the Performance Delivered Insider Secrets for Digital Marketing Success podcast, where we talk with marketing and agency executives and learn how they build successful businesses and their personal brand. I’m your host Steffen Horst. The topic for today’s episode is defining digital marketing success for the fashion tech industry. Here to speak with me is David Cunningham, who is the President of Brand Partnerships for MySureFit, a disruptive digital platform for shoppers and fashion brands. 

David is a 20 year veteran of the apparel industry. He has held senior positions at some of the world’s top fashion brands, including Ralph Lauren, Calvin Klein, Tommy Hilfiger, and Kenneth Cole. In his current role, David oversees business development opportunities in both b2b and b2c channels, developing programs to improve shopper experience, and e-commerce supply chains while improving the industry’s carbon impact. David, welcome to the show.

David Cunningham: Thank you very much for having me.

Steffen: Now, David, before we, before we talk about today’s topic, tell our listeners a little bit about yourself. How did you get started in your career and what drove you to marketing?

David: Okay, I started out, as you had mentioned, some of the brands I worked for I started at Tommy Hilfiger. And believe it or not, I started at Tommy back when no one could pronounce his last name. And there were 100 people in the company, including Tommy and his wife, or his first wife at the time. And we were not a startup, he had had some success, but certainly nothing to the extent that he’s known now, internationally. So it was a great kind of proving ground and a learning experience for somebody right out of college. 

I started with him in a merchandise coordinator position where I was really going out into the public in department stores where he was building shopping shops, speaking to customers, training staff, teaching them what Tommy Hilfiger was, what the lifestyle was. And then it evolved over the course of the 12 years, I was with him to heading up a division for the company. But I had various roles throughout and everything that you do in the fashion industry, particularly when you start out out store line, and then work with a company that’s growing as fast as he grew. 

Everything’s marketing based, whether it was I was in sales, or merchandising or store planning, everything had a marketing base that everything sat on top of because he was very much about this was his vision, he wanted to make sure whatever happened in the design studio was interpreted all the way down to the customer. So marketing with him started from the time that he would design something. From that point forward, it was all about how are we going to get the message out. From there, I went on to various positions with Kenneth Cole, I ran his division of apparel and introduced the apparel line to basically the world. Introduced the women’s division after we started the men’s division. 

Then from there went on to Calvin Klein, I ran the jeans division for Calvin Klein, doing international, as well as domestic. The international side, it was interesting, because when I took it over, one of the things I noticed that the brand looked completely different in Europe, in Asia, and in South America than it did in North America. So from a marketing standpoint, one of the first things that I had to get my arms around was, we have to have specific branding. We have to have specific messaging. It all needs to start with one vision, and then that needs to be interpreted around the world. Some of the best brands in the world, you walk into a store, no matter where you are, you could be blindfolded. 

And you look at the product, even without labels on it. And you know exactly what brand it is because it’s such consistency. That was not the case in Calvin Klein Jeans. So we worked very diligently to make sure that messaging was the same everywhere. And we were quite successful doing that. From there I went on to Ralph Lauren, which is probably the quintessential marketing brand, international message that is consistent no matter where you go. So the example that I had said earlier about walking into a store looking at a product and knowing that it’s the brand. I think that Ralph Lauren epitomizes that no matter where they are. And again with Ralph, similar to what I had mentioned earlier with Tommy, it’s all about marketing from the moment that he starts designing something. 

He’s already thinking, how am I going to get that message out and every brand in the portfolio of Ralph Lauren brands has a very specific part that they play. And no, they do not cross over each other. And his son David is very his he oversees all that. So he’s very good and very keen at making sure that every part of the Ralph Lauren family of brands stays in its lane. So that we are or they are taking care of the customer from an opening price point, hat would be Chaps all the way up to Purple Label. That would be a very high end, Ralph Lauren store or very high end boutique. But everywhere in between, there’s a product that fits the customer’s needs.

Steffen: Now David, from Tommy Hilfiger, two, Ralph Lauren, your career in the fashion industry has spent extensively across the retail space? How have you experienced growing these brands led you to think about the brand customer relationship?

David: Well, that’s it actually, it’s a great question. And I think that the fashion business, very successful fashion brand has to always be thinking of who their core customer is. And brands that tend to kind of fall off the mark or fall out of favor, are the ones that I think tend to try to broaden their their reach a little bit too much. One of the examples that I’ll give is, I think if you look at a brand like Nautica, which had a very strong business in outerwear, and swimwear was competing with Ralph Lauren and Tommy Hilfiger, back in the day in the 80s, and the 90s. It was the big three. I think where they might have had a stumble was that then they tried to start being all things to all people, and you alienate your core customer. 

And the new customer that you get, is not necessarily going to be as loyal as your core customer base was. So as you go after that other customer base, you kind of start losing your core customer. And then you’re kind of left with nothing as that one customer moves on to the next trend or whatever it is. Fashion. Yes, you want trendy apparel. And yes, you want things to keep changing and evolving. But you really have to stay to what’s the essence of your brand, and the Gucci’s of the world, the Burberry’s of the world, the Ralph Lauren’s of the world. They all understand that. And that’s why they’ve been able to last as many years as they have.

Steffen: When you say that, I mean, that makes me think that expanding your area of service or who you service is not always a good idea. But that would also limit companies and then we’ll just keep them where they started off. Are you basically saying they should just focus on on where they started off and not expand? Or is there a special approach to expanding and going into other areas and then trying to attract new customer customer groups?

David: Yeah, there is then you can do. Like, you can do an infusion of your brand to go after a specific demographic. So for instance, when I think Burberry did a very good job of doing this. So Burberry had a very conservative British heritage, which it still does, but then they decided that they needed to maybe start becoming a little bit hipper and a little bit younger. But they still at the end of the day, they kept to who they are, they kept their heritage. So they were getting a younger customer, they were getting a hipper customer, but they didn’t necessarily chase that customer, as much as they told that customer that hey, look at what we have, and look at who we are. 

But at the end of the day, they still kept the DNA of the brand. And that’s the key, you have to keep that DNA. And you can try to get the younger, hipper, trendier customer but never chase them. Get the message to them, get them excited about what you’re offering, make it relevant to them. But as soon as they feel that you’re starting to pander to them or chase them, then that’s back to that what I had said earlier, you lose your core customer. And that person that you’re chasing will end up walking away eventually and then you’re kind of left with nothing and trying to reinvent yourself and chase your core customer. So it’s all about keeping true to your DNA.

Steffen: Yeah, yeah. And that usually is a slow transition. I mean, it’s nothing you just force right? You just said remind me, I used to work at DaimlerChrysler in Stuttgart back in, gosh, 2000, 2001 time. And they were in Germany known as you know, brand for older people, because of the design of their cars, and they had a really strong, you know, grip of that market, but they wanted to engage with the younger audience. 

So over, I think two or three periods, when they kind of changed out the cars, they just modernized the car and make them fresher, they still had elements that, you know, their core audience loves, like the wood paneling in the car and other more traditional elements, but the design and other things in the car, they have kind of I wouldn’t call it revamp, but the freshened it up, you know? And then that’s how they basically engaged with a younger audience at the end of the day. And I think it’s probably similar to what you just explained.

David: Yeah. And I think that you’re it’s true across many different industries. And another example of that is Cadillac, with their sedan kept trying and trying and trying to compete with BMW and get that younger, upwardly mobile professional to leave the BMW and go after a Cadillac. And they even change their marketing. And they went after kind of almost rebranding themselves. It wasn’t until they started introducing the Escalade and other SUVs that gave them some heft, that then they started getting a younger customer base. But they I don’t think that it was thought out, as well as the example that you gave, of the steps that they needed to do in order to get that younger customer. And I still say that now, you’d still find hard pressed to find a younger customer buying a sedan from Cadillac, but they will by the Escalade.

Steffen: Yeah, yeah, I can totally see that. Now, from when you started, marketing practices have changed dramatically, most notably, as digital marketing has become a cornerstone piece of sales and customer acquisition tactics. Can you talk about what the transformation has looked like over the years?

David: Sure. So back in the day, you know, marketing was in store marketing, where you had great aspirational shots of models wearing the clothes that people were drawn to, and would see and say, I want to look like that. And see it in a magazine, I want to look like that. See on a billboard. Now, because of the digital age because of social media, because of people sharing Instagram shots, and everybody wants to be famous, you now have to give them something through digital marketing that makes them stop and think, hey, that’s different. That’s interesting. That’ll make me stand out. 

And what is it about that that does it? It’s clever, it’s humorous, it’s short, the attention span is so quick, that when you’re doing any kind of digital marketing, no one’s going to give you more than probably at the most, maybe 90 seconds, they’re going to look at it, they’re gonna swipe it, if they find something in it in 20 seconds, or maybe even 30 seconds that interests them, they may click through to see the next thing, but you’ve got to grab them immediately. And we constantly at MySureFit are always doing A/B testing to say, okay, if we think that this is a great way to get somebody engaged, let’s do this version and that version, and then just watch. 

And you will know, within 24 to 48 hours, where you need to change your approach, based on the response. How long they looked at it, did they click through? Who clicked through? Once they click through where they engaged with what they saw or did they immediately jump? That back in the day, you never got that feedback that quick. So I find it yes, it’s a challenge. And yes, it’s exciting that it’s a challenge. But it’s much more efficient. The marketing now, because like I said, it’s almost immediate feedback where you can make changes on the fly. And in the long run, you’re going to be much more efficient with your spend. Because you don’t have to wait 30 days to find out if it’s working or not.

Steffen: Yeah, that’s a good point you just made. I mean, it’s just I mean, I don’t know necessarily how it was in the 1980s, 90s. Right, but it’s so much louder out there, right? There’s so many brands, so many different things that shout you and want to send messages to you that you just need to stick out of the noise with something that is clever and interesting for your target audience in order to attract them. And then use, as you said, the few seconds that you get to make an impact.

David: Right. And in the apparel space in particular, there’s so many startups that are ecommerce only. And you know, back in the day, you used to have to find a retailer that would be interested enough to buy your product and have to buy your inventory. They’d have to display your inventory. If your inventory didn’t sell at the rate they wanted, you either had to take it back, or you had to give them money for them to mark it out of stock in order for them to buy more. Now, people completely don’t even use third party, they go directly to the consumer. And it’s much more efficient. It also allows for tremendous creativity. 

Some of the things that I see on Instagram, for instance, that that someone has just come up with that, hey, here’s this really great product, why don’t you try it, and then all of a sudden, it takes off. There’s a couple of different companies that I can think of that started with one product category. And now they have multi products that they do, some of them even have freestanding stores now, where they everything was just based on ecom. So it’s almost like the reverse. It was from brick and mortar to ecom. And now it’s ecom to you get enough of a customer base, then they’re going to want pop up shops, or they’re going to want a in certain markets, they may want a brick and mortar outlet.

Steffen: You know, you can you can test so much quicker if a product finds an audience, right. Because as you said, you can engage with your target audience or the target audience that you deem is perfect for your product so much quicker. And then you get relatively soon feedback on whether it sticks. If it doesn’t stick then you go back to the drawing board. Or if it sticks, as you said, you know, you move on to the next level and push it out further. Go, you know, brick and mortar or whatever you want to do to to kind of grow your audience and grow revenue. Now, as the fashion industry continues to innovate, there’s been a big focus on new virtual digital focused resources for shoppers, specifically, a crop of companies offering virtual fitting rooms. Can you explain this phenomenon? And how how does MySureFit’s offer is different from other marketplaces?

David: Sure. So if you think about the way that people used to shop, they would go into a brick and mortar establishment, they would be greeted, they would go to a rack, they would start looking at stuff, someone would come up to them and say, would you like me to start a fitting room? Sure, I’ll start a fitting room. They would start taking stuff from you and put it into the fitting room, you’d go into the fitting room you’d try them on. If you were shopping with friends, you’d come out and show them. You’d go back in, just make outfits out of the things that you picked out, look in the mirror again, maybe have your friends give you comments, and then take your purchases to the register and leave the store. 

Now that everybody for the most part is shopping, virtually, MySureFit came up with technology that mimics that whole process, but then it does it one better. So the biggest problem with ecom apparel shopping right now is there’s a phenomenon known as bracketing. Where a customer will buy two or three of the same item in various sizes because A either they’re not used to the brand B they’re not sure of the cut, or C, they want to know if well, maybe I want it to fit looser, maybe I want it to fit tighter. But if I have free shipping to and from, it doesn’t matter. The inconvenience is I have to put it back into a box and I have to drop it off out front for someone to pick up or I have to take it to the post office or wherever. 

People now are thinking from the convenience of shopping from your house. That’s not that much of an inconvenience to have to return something if it doesn’t cost them any money. So what MySureFit has done is said, if that’s the case, as we know that it is, and that returns due to sizing run almost 50% or more then we thought, hey, you know what, there’s got to be a digital way to do this. So what our technology does is unlike some of the competitors in this space that use a self reported measurements where they ask you to measure your certain body parts and then put it onto their screen. Or they use an avatar that’s supposed to mimic what you think your body looks like. We actually asked our customers to take two selfies. 

We have over 100 fit points that we are digitally fitting and then through artificial intelligence, we can match that with various brands across various classifications and recommend their sizing with a 99% accuracy. So the returns due to sizing goes down to below 5%. So if you think about that, just from a profitability standpoint, you’re over 50% now, and a lot of companies just assume that’s the cost of doing business. And we’re going to take it down to less than 5%. So all that profitability goes right to your bottom line. Once the customer has shopped, or picked their items that they are interested in, it goes into our virtual fitting room, which we call a smart fitting room. 

Unlike some people who have this technology, our technology is such that you actually see your image. And then you pick the items and you can put it on your image, you can make outfits, you can match different brands across outfits. So a skirt from Zara, a top from H&M per se, and see what it looks like. We have a social media button that you can then share those images with your friends. So they can give you feedback immediately. After that takes place, then you end up going into putting into your shopping cart. And then when you’re buying it, you know, A I know how it’s gonna look on me, because I’ve already seen it on me virtually. And B I know it’s gonna fit. 

So the amount of anticipation of getting that box in the mail versus that, oh, I hope it fits. The I hope it fits has gone because you know exactly what it’s going to fit. And you know, it’s going to look great on you. No one else in this space is doing all of those things that we are. The other thing that we’ve done is we’ve taken it a step further. And we’ve developed a smart stylist, which is a curated closet, as it were. So as our artificial intelligence learns from you, the more you shop, we also start being able to give you recommendations of what we know that you like this fit, we know you like this brand. 

Here’s some other brands you should look at, here’s some other fits that we think will be complementary to everything that was measured on you, and you walk onto the site, and you can go into that closet and see everything that’s already there. In addition to that, we keep track of the things that you bought. So say you bought a black skirt, we can give you oh, based on what you bought before, here’s some recommendations of other things that you may like that will go with your past purchases. So again, it’s like having a very, very good salesperson in a very good boutique. Like a Neiman Marcus type of salesperson who’s gonna say, hey, by the way, I have everything you’ve ever bought from us, right here. And here’s some new stuff.

Steffen: Well, that sounds like a great, great solution. I think the fact that costs are reduced for the company, for the seller is I think a big thing. I mean, when you when you talked about the behavior these days in regards to ecommerce shopping, and I see that on my wife, right? They buy a lot, and then it gets delivered the boxes stack up. Right. And at some point it has to be returned. Right, right. I mean, it’s for us the consumer, it is convenience, right? Because as you said, you order two, three different sizes, because you’re not quite sure. Whe I order Adidas shoes, I know that sometimes they run the size smaller, you know, like for some others, they might be the right fit for the 12 that I get right. So that definitely seems to be a great solution to help not only companies but also the customer at the end of the day. Or the husbands. No offense.

David: Right. Deal with all those boxes. Yeah, I have two daughters and a wife who do the same thing. So I completely feel your pain.

Steffen: Yeah. Well, you know, there are lots of conversations. And that’s that’s really a topic that becomes more and more important for companies. this year. Lots of conversations around the disappearance of third party cookies, which will you know, as you know, as I know, change how brands and companies do advertising. How they collect and use customer data in order to enhance the digital marketing and sales tactics. Now, how does My SureFit help companies overcome that challenge?

David: Yeah, so we actually have a couple of really interesting things and because everything that we do is artificial intelligence and machine learning. What we can provide our brand and retail partners when they use our technology on their site, is we can give them not only here’s what the customer bought, but we can also tell them, here’s what the customer bought and tried on in the fitting room. And this is what they put back and this is what they liked. And this is what they paired with that. Which may seem on the surface like that may not be be that much information that a retailer or a brand would use quickly. But if you think about it the way that the fashion industry works, where it’s 6, 8, 12 months out from a development standpoint. 

If you’re getting live information about customers’ preferences, and you have things that you’re getting ready to put into production, whichever factory around the world that you’re using, and you have this information that you can make changes immediately on, before you put in a production run, you’re so much more efficient when stuff comes back in. You’re also so much more efficient when it comes to the amount of inventory that you’ll carry on any one style based on the information that the customer is giving you. Right away. Back in the day before the Econ business took off. And before the digital marketing and digital imagery became so important, you would almost have to wait until you looked at a sale rack in a store to know what didn’t work. 

Because you’ll see what the customers passed on not only from the color not only from the fabric, but also from the sizing, then you had to adjust it. So that’s about a year out before you can make any meaningful changes, because that’s how long it takes to gather that information, interpret the information, and then change anything that’s in the production line. With our information, it happens very, very quickly. On the other hand, the other part of that is also because we have all this information we’re gathering and we have a smart stylist that is doing a curation in wardrobing. 

Our artificial intelligence is already thinking, well, if they like A, then they’ll like B, but maybe we’ll try C as well, because that might be the progression of where their thought processes based on the other things I’ve looked at. Maybe not they didn’t buy it. But they paused on it long enough as they were shopping, that they have some interest in that. So let’s throw something like that into that wardrobe and see if that’s something that they want. So we’re learning as the customer is experiencing the shopping, we’re actually learning from them without being able to sit and talk to them like a salesperson would. But we can digitally figure out where their preferences are.

Steffen: That is really interesting, because I would assume that also limits the the wastage when it comes to clothes production, right? I mean, how many pieces are being thrown away? Because no one wanted it, even after they were put on sale and ridiculous discounts. So before we before we come to an end, David, and this is a great conversation, I wished we had more time. But more and more we’re seeing the fusion of technology to enhance in person digital shopping practices. Can you discuss the multi level strategy of defining a digital marketing process that combines both fashion and technology sectors?

David: Yeah, so what I would what I would say is that the best way from a digital marketing standpoint for us to react to consumers is through learning their behaviors and learning their behaviors through our site is allowing us through the process of how they shop and what they shop and what they pause on. It’s it allows us to think more on in the future, this customer likes A. So when we start doing digital marketing, we can take the customers who have a preference for that one item, that one style, that one brand, that one look, and we can fine tune our messaging to them. And do that again and again and again, depending on what we see with the progress of how they’re shopping. 

So we currently have a b2c site where we have hundreds of brands and 1000s of styles on the site that we’re allowing customers to come and experience our digital fit and our digital, our smart fitting room and our smart stylist across a bunch of different brands. Because what we want to do is to get the word out to the consumer that hey, this is a new way to shop. As that develops, which it has continued over the last three years, we keep refining it and putting out new versions and again and again and and fine tuning. And we’re now at the point where we’re going to retailers and we’re going to brands and saying hey, you should get this on your site. 

So our technology is packaged in such a way, it can be put on to anybody’s current ecom site. It’s just basically a plugin that goes right into their site, they’ll see a small icon that says MySureFit. If a customer is already registered with MySureFit they click on the icon they put in their login credentials and they’re ready to shop anybody’s site with the fit and the fitting room and the wardrobe. All of that information that we get can also be used in digital marketing. So for instance, if Nordstrom which now has a version of curated wardrobes that they send out in the trunk, all this information that we have will make them be able to put together that curated wardrobe even more efficiently than they’re able to do it now. Because again, we’re getting very, our information is so fine tuned, that we can give them not only brands, but styles, colors, and sizing that they may not be able to get their hands on right now.

Steffen: Well, I could assume you guys are really busy, because this sounds like a great technology to really help a lot of fashion retailers to, as I said earlier, to reduce costs to reduce wastage and basically add to the bottom line, but more importantly, help the customers find the right products that fit them in the first place.

David: Yeah, here’s the interesting thing about the fashion industry is that the fashion industry as much as they think that they’re forward thinking on a whole, they tend to be very slow when it comes to adopting technology. And during the pandemic, when the ecom business took off faster than any retailer or fashion brand could have imagined. They’re now kind of playing catch up, where they’re starting to look at it and say, okay, now in inherently, there’s some issues with this huge ecom business that came out of nowhere. And we have to figure out what we need to do in order to A bring the cost down, B to be more sustainable, C, to service our customer better, and have our site stand out more than anyone else’s, because we’re offering things that no one else is offering. 

We have all those answers for them. It’s just a question of getting them to the point where they feel we’re ready to accept this information. And we’re ready to move forward. The technology that we’ve we have we’ve been developing for seven years, it would be virtually impossible for anybody to step into this right now and say, oh, I can probably do that too. So it’s it’s years and years and years of research and years of programming and going and talking to consumers and photographing consumers and then turning it into digital. And we don’t even need spec sheets from retailers or brands. We don’t have to measure the garments we, our technology can look at a picture on their website of a garment, and we can come up with all the specs on it and match it to someone’s body.

Steffen: Wow. David, thank you for joining me on the Performance Delivered podcast. I’ve really enjoyed our conversation. If people want to find out more about you and MySureFit, how can they get in touch?

David: I’m on LinkedIn, so they can reach me at David Cunningham on LinkedIn. They also can reach us at And if they want to experience the b2c side, it’s

Steffen: Perfect. Well, thanks everyone for listening. If you liked the Performance Delivered podcast, please subscribe to us and leave us a review on iTunes or your favorite podcast application. If you want to find out more about Symphonic Digital, you can visit us at or follow us on Twitter at Symphonic HQ. Thanks again and see you next time.

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