Rethinking Retail Marketing Leadership: AI and the Fractional Revolution

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Fractional CMOs with blue-chip experience are sources of enterprise-level talent accessible even to mid-market companies. Couple that resource with AI tools that are moving at the speed of light, these strategic co-pilots are separating marketing winners from losers. With the explosion of video channel fragmentation creating a measurement nightmare and threatening attribution accuracy, and retail media networks evolving from a “necessary evil” into precision targeting powerhouses – both demand a new level of marketing expertise. Join Shelley and Lindsey Scheftic, CMO, Owner and Founder of The CMO Sidekick as they explore how marketing expertise is being fundamentally redefined. The traditional career path is dead, yesterday’s marketing education is obsolete, and 65 percent of future marketing roles don’t even exist today. Listen in to this provocative conversation to get up to speed on the future of marketing.

Special Guests

Lindsey Scheftic: CMO, Owner and Founder, The CMO Sidekick  

Transcript by Descript:

I think that the marketplace is going to drive hard to just continue to make those tools better, uh, to, to make great creative and. Um, yeah, I can’t wait. We gotta, we’re going to meet another year and a half and we got to be like, okay, what were we doing a year and a half ago? It’s a great point in time when there’s just so much technology.

Retail Unwrapped is a weekly podcast hosted by Shelley Cohan from The Robin Report. Each episode dives into the latest trends and developments in the retail industry. Join them as they discuss interesting topics and interview industry leaders, keeping you in the loop with everything retail.  Hi, everybody.

And thanks for joining our weekly podcast.  I’m Shelly Cohan, and I’m very excited to welcome back Lindsey  Sheftick, Chief Marketing Officer, also owner and founder of the CMO Sidekick. So I am so thrilled to have you back on Retail Unwrapped. And we’re going to be discussing the world of Marketing 2. 0.

Well, it should be like 10. 0 at this point. But remember, Lindsay, last time I had you on a year ago, about a year ago, uh, we had so much information, we had so much fun, we actually had to take the podcast and divide it into two podcasts.  I love that. Let’s say thank you for having me. I’m so excited to be back.

I’m so excited to see you and tell you all the things I’ve been up to and what’s happening in the world of marketing. Um, so yeah, maybe we can go for a three peat this time. Maybe we can get into a three episode series.  Yes. Wouldn’t that be great?  So I remember about a year and a half ago, you founded your company, which is kind of like this on demand CMO.

So tell me about this idea of fat fractional C suite and really how it has involved over the past year.  Yeah. You know, when I first started doing this about a year and a half ago,  You know, I was meeting a lot of people in the space who were kind of doing the same things. And I would say it has grown so much in the last year and a half.

First of all, I go to lots of events. I was out at, uh, last year I was out at Cannes. Um, I was at possible. I was just at CES and pretty much every marketer I meet is like, Oh my God, I’m so jealous. How can I do what you do? And I have been advising lots of other marketers. at my level, how they can go out in the marketplace, how they can be an on demand CMO.

Um, you know, what my experience has been and, you know, how kind of best to serve clients. And so I think that it’s becoming definitely more commonplace and not just, um, I would say. In the CMO position, I’ve, I’ve met lots of CROs, CCOs, um, you know, people who are looking to have gig work and create impact across multiple companies.

And it seems to be working well. Um, I know the clients that I service big and small, I think that, you know, them having me fractionally and being able to take my experience and have a really big impact and kind of. Put what they would have put toward a full time salary to someone with my level of experience I’m still able to kind of get in there and maybe even make a bigger impact be more strategic Kind of somewhat be advisor to some of the CEOs I work with on their business  And and just really create a value even if they just have part of my time, so  I’ve seen it just really kind of explode over there last year and I feel like I was Part of being in the front end of that.

And that’s really exciting and, and, uh, fun. And I’m always trying to recruit people over and say, you can do it. It’s so fun and you can own your own business and it’s okay to cut the ties or cut off the golden handcuffs. Um, because I’ve just seen a lot of success and, um, and doing what I’m doing now.

That’s great. And I have to remind our listeners, cause I know you won’t toot your own horn, but I can toot your own horn. And so you. We’re CMO at Amazon, Ring, that was a big one, Red Bull, Vans, uh, Apple, AT& T. I mean, you have some really big brand name experience behind you. So do you think that, um, why is it so important in today’s business landscape, this fractional C suite?

I think it helps democratize marketing expertise and help, you know, I think before, if you think about companies who are up and coming. And they can’t afford to hire. You know, a blue chip CMO, people who have worked at those types of brands full time, they just could not be competitive in this marketplace on salary, on comp, on, um, equity.

And I think that it helps democratize some of these midsize businesses or businesses that are growing. I think about on the consumer side and also on the B to B side, um, I think that having access to talent fractionally is a game changer in this marketplace for companies that are cutting headcount, you know, aren’t maybe investing as much in marketing, but still need the strategic level of support and help to get their business off the ground or through a hard spot.

Um, and so that’s, I think why You know, this has kind of been a game changer in the marketplace and. And that it’s just becoming more acceptable, you know, two years ago, three years ago, if you’re kind of like, Oh, I’m freelancing. People were like, they’re in between jobs. They’re out of work, but with the tenure of the CMO being 18 months, 24 months, I think is, I think 18 is average.

Wow. There’s kind of no difference. Like why put all the eggs in a basket, one basket. And then you’re looking for your next gig or you’re there, you know, 16 months. You’re like, okay, my time is running out. I got to look for the next thing. And so I think that CMOs are getting kind of smart to, to recognize maybe I can split up my time across multiple businesses, still be as successful financially.

And make a bigger impact at some of these, um, companies, big and small. So, I think that’s Well, Lindsey,  I, I’m so proud of you. I think that’s awesome. I love it. And I hope you inspire more people to do it. Um, I think, so here’s my, here’s my premonition on the new hottest C fractional sweet job, the, uh, chief geopolitical officer.

Yeah, yeah. I think that’s probably pretty timely right now, I would say.  Yeah. So anyway, what I really love to do is I want to get your kind of view on the current state of using AI. I know you’re an AI enthusiast.  Um, but what’s going on with AI and marketing and maybe you can tell us a little bit about some use cases of where AI is really working well and marketing and maybe some areas that have fallen flat over the past few years.

Yeah, you know, man, it’s so wild. I think back to when we first spoke and, um, a year and a half ago, and I was just really starting to use AI. I think everybody was and I, um,  it is so integral to my business and how I work and how I think and how I can take my thinking to the next level. Um, you know, I would say my right hand strategist is Claude, um, which is part of the topic.

I love Claude. I think it’s an amazing tool for marketing. I talked to lots of marketers who are on chat, GBT, and I was like, no, no, no, no, no, no, you got to switch. You got to switch. It’s just. For me, uh, it’s a great tool to bounce strategy off of, to kind of get gut check, you know, I do, um, you know, I’m creating strategic documents and then I’m basically using it to help draft and do, you know, finalize drafts, help take notes.

Um, I also love a tool called read. ai. I, I think it is pretty commonplace now to get on a call and it’s recorded that there’s an AI assistant on the call. Um, to me, that’s a  total game changer as well. Like I love being, having access to my transcripts, being able to take my transcripts and put those in the cloud and distill, you know, really good, um, pieces of information for clients.

Uh, being able to, you know, sometimes when you’re on a call and you say something and you sound super smart. But then you can’t replicate what that is again. Well, now you can. I go all the time, download my transcripts. I’ll put them in the cloud and I’ll say, Hey, what was that really smart thing that I told the client at about the 27 minute mark?

And then it pulls it right out. And I can still use that information versus just going out in the world and then, uh, you know, forgetting and not being able to replicate what I said exactly on a call. So those I think are my big. Two to go to, you know, my go to’s that I’m using, um, Shelly, have you heard a gamma before?

No. Oh my gosh. Actually, I think, I think one of the professors at FIT who is, uh, in the math department, I think I, he mentioned gamma. What is it?  Gamma basically can create PowerPoints for you.  Oh, nice. I used, over the last year and a half, probably 15 different tools. And I think Gamma has just risen to the top for me.

It’s very dynamic, it’s very fast, it’s very easy to use. You know, a year ago I was like, Ugh, I just want to put like, slide scripts into a tool and then just have it spit me out the slides. Like, why can’t anything do that yet? Well, it’s here. Um, so Gamma is one that I’m really, uh, enjoying using. Um, so those are like, I would say my top three tools.

And then, you know, I’m actually using a lot of AI with some of my clients. So I work with a client, um, named a Domini. They’re a digital, uh, out of home and kind of smart video everywhere platform. Um, and we have been training a model. I’ve been working with their team to who’s developing the model to train a model, to build, um, dynamic strategy for video.

placements for media planning, for optimization, for measurement. And that has been so exciting to  be able to peek behind the curtain into something that’s being active, actively built and to help kind of. You know, give my expertise in, um, in building that. So, uh, that product they’ve named Jean, J E E N,  um, and it’s, uh, it’s, I think it’s going to be a pretty cool, uh, piece of technology to use, um, for, for planning media and video, video content.

That’s amazing. Have you heard of a gentic? I’m sure you have. What’s your view on agentic AI and what’s the use case for that for marketing?  I haven’t used agentic. Um, I haven’t used that one yet. Uh, you know, I think that I am, uh,  I’m, I, I kind of got my go to’s and then I’m testing kind of new ones all the time, but I haven’t used that one yet.

I think it has to do, I think it, maybe I’m not, it’s agentic, so like an agent, it’s using agent AI, and, uh, a lot of, uh, retailers are using it in the shopping journey for conversational commerce. Okay, got it. Yeah, to kind of up the game there like almost like a a bot basically.  Yeah, a sophisticated bot.

Exactly Feels like you’re talking to a human. Oh  I don’t know about you, but I hate being on the other end of talking to not a human. I still think there’s value in human interaction. I still think, you know, something I’m also not a fan of is just the, uh, the podcasts that are auto generated with AI. It just, there’s something about humans talking to each other.

It just feels a little inauthentic.  It feels manufactured because it is. And I still do think that A. I. Is used the best with human interaction with human training. You know,  I work on these documents all the time and it’s wrong all the time. You know, you wouldn’t know. You didn’t have the experience and to be able to kind of Retrain it or wield it into the right direction.

So, you know, I was just doing some analysis this morning and it was like, no, your math is wrong. And I was like, Oh, I apologize. My math is wrong. So, you know, you can’t, it’s not foolproof. You still have to double check your work. And, um, I, again, at the beginning said I use it as like a gut check, um, because it’s not always right.

Yeah. Yeah, that’s true. And remember, uh, a year and a half ago when we met, like the whole conversation, um, at the conference I met you at was all about, CMOs being replaced with AI. And now, as we’re sitting here today and we’re reflecting back and just listening to what you said, that’s simply not going to happen.

Yes, it’s going to replace some of the mundane stuff we’re doing, but you know, you’re right, there’s got to be a balance between the human and the AI kind of, you know, working together. Totally. I think that, I think it’s going to get smarter and smarter and smarter. But it’s, I don’t think it will be foolproof.

I still think you need somebody to direct it. And, you know, I think that,  um, I worry sometimes for the younger generation that they will just take what is given to them at face value and not learn. And so I still believe that there’s value in. Mentorship and marketing and training and not having AI train the humans.

It should be the other way around. And, you know, totally agree. Like mundane things. It’s fantastic for, you know, I mean, I use it like to summarize my expense reports and make expense reports for me. I just upload all my receipts and have it do it. Like that’s something that is just mundane. It takes a lot of time.

I do that, you know, then I can move that task off my plate in 30 seconds and. Um, move on to the next thing. So it’s amazing. Oh, my God. You probably just gave all our listeners the biggest tip ever. Like, I haven’t even, I haven’t even done that. That’s amazing. Yeah, it’s a good, that’s a good, that’s a good one.

That’s a great hack. Just shortcut everything in my life. So  I love it. So I’m hearing all this buzz about, you know, video fragmentation. Can you tell us what it is in layman terms and what’s going on in this area? And what should retailers and marketers be thinking about with video fragmentation?  Wow, there are, what a can of worms, Shelley.

There are so many ways to buy video now and video advertising, and I don’t even think, I don’t even think most advertisers can keep it. You have streaming, you have OTT, you have direct, you have CTV, you have through programmatic. Um, there’s so many ways to buy and so many different types of media to buy.

Um, that it’s just become very confusing and the marketplace or marketers to figure out, you know,  like, where do I place my bets? Where do I put, put my money? Um, you know, there used to be, I think, a lot of value  in going direct to, uh, you know, the, who, who’s the SPNs  even now you can buy like Netflix, which is newer, um, to buy Amazon prime.

Um, but now you can also buy. These, um, these, you know, video suppliers and all different types of places on OpenExchange and DSP and SMPs,  um, and so I think that, um, right now we’re kind of just seeing a lot of fragmentation, but I have a feeling over the next year or two that there will hopefully be some consolidation of some of these partners coming together because It is very hard for marketers to figure out where do I spend my dollars?

What CPM where,  if I have a low CPM here and I’m on a DSP, am I getting premium supply? Where am I showing up? Um, it just seems like it’s very hard to, to police at the moment. Um, and then you have retailers who. Like Walmart, who,  with the Vizio, um, and you have partners like T Mobile that just bought Vistar.

That’s just more areas, right, where video advertising is becoming more fragmented. Um, and brands are starting to add video, you know, sell video advertising as part of their offerings as well. So, it’s just a really interesting world I think we’re in right now, and there’s lots of options. But I’m hoping in the next year or two that, you know, and everyone’s talking about fragmentation, that there is consolidation or there are partners that really start to bring,  um, bring these kind of disparate ways that you buy advertising together and then bring measurement all under one umbrella too.

Yeah, that makes sense. It seems very complex right now.  Yeah, I mean, especially on the measurement side, like if you’re buying.  Well, measurement and also duplication of audience, you have audiences watching in multiple places. So, you know, how do you police that? And, um,  yeah, it’s, uh, it’s definitely a very interesting time.

I also feel like the way, you know, you have agencies that are buying and hold codes in different ways versus like boutiques. Or even clients, some client side, they’re buying a couple of channels here and a couple of channels here and a couple of channels here. And so like, how do you pull that kind of reporting together?

And, um, and how do you kind of start to, how are, how are vendors going to kind of start to solve for some of those pain points for advertisers? Because. They’re just too many options right now. Yeah. I want to ask you about retail media networks. So, this has really grown over the past couple of years, and initially it was really used as a revenue stream for retailers, you know, to sell advertising space.

Um, but what I’m seeing now is that companies are really trying to better optimize retail media networks to really kind of deepen their relationship with the target market and drive better personalization. What are you seeing in this space, and what’s the new era of retail media networks? Man, I, I love this topic because I feel like just even two years ago that as a marketer, like on the  kind of on the CMO side, maybe you oversaw retail marketing or maybe your retail marketing was part of your sales team that you were kind of forced to buy it, right?

Like to pay to play, you want to get into target, you want good shelf space, you want Walmart, all the same, right? Home Depot, you had to spend X amount of dollars on their retail networks. Now, advertisers like myself, you want to spend your dollars there. The retailers, I think, have done a phenomenal job of getting the segmentation better.

I mean, they’re sitting on a treasure trove of customer data with habits that they weren’t really utilizing before. Now they’re utilizing that. And then they’re expanding out from just site. Or from, you know, just in store to other places like CTV, for example. And, um, and even digital out of home, like near around store.

And so I think that there’s just, um, it’s just a place where you can get somebody right at point of purchase and are close and be able to close that loop. On measurement with Cercana, with other measures, with Cochaba, with other measurement and, um, and you’re just getting a much better idea of incrementality and what you’re driving at a specific retailer now with Retail Media Network.

So I’m excited to see that they’ve like turned it around. Um, I see marketers like very excited to  buy retail media where before it was kind of like a,  you had to buy it. Now you want to buy it. Um. And I’m glad that the retailers are really sharpening their pencil on their offerings because I do think it’s not just an additive revenue stream, it’s probably something that could drive their business, um, forward into the future.

So, um, so yeah, I think this space has gotten really interesting.  I love the fact that I actually think it’s better for the consumer. I think about it, it’s the consumer that is benefiting from all the personalization. That’s, that’s what it’s really about. Totally. I love it. I love that. I like the personalization when I’m going to buy something when I went into Target,  they know what I’m there to buy.

I have my two kids. They know I’m, they know exactly where I’m going. I’m going to get hit with a toy ad. I’m going to buy some bananas. They know exactly how to, you know, to hit me up with the right messages before I come into store. And even when I’m there. So, um, I love it.  It’s so interesting. Cause you know, you’re right.

Like right now I, I go to CVS to get my, you know, prescriptions or whatever. Um, it’s a local drugstore near my house, and like, it’s so annoying that I’m sitting there with my phone and I’m just scrolling through the coupons. It’s like, you know, a 12 minute odyssey of stuff that I’m, I just keep scrolling, but I can’t not scroll through it.

It would be great if they could just send me They know what I shop. They know everything. Why not just send me a nice little 10 coupons that I can quickly use. I mean, so. Kind of does in their app was circle and you can just, I just stand at the, the, the registered. I’m like. Apply, apply, apply, apply, apply.

Um, but, and sometimes it makes, drives me back into the store to go buy something that I was like, Oh, well, there’s a coupon I can, you know,  coupon mom, I’m in my coupon era. Yeah. I love it.  Listen, we all like to save money. So,  um,  so I have to ask you to look into your crystal ball and tell us where is marketing headed into the future and what best bets to make in marketing over the next year, what are they?

So I see, I think, um, you know, we did, we were talking a little bit about AI and we were talking about cloud and how I’m kind of using it for strategy and other things. And I think something we didn’t talk about was just.  Creative and how it’s being used to make more contextual creative. I do believe something we talked about a year and a half ago, but it was so in such its infancy and it’s getting so much better now.

Um, I think just some of the, uh, template generation that’s coming out of it. Um, you know, there’s so many great tools out there. And I think and great tools to make video content to edit video content I think, you know, I work with some smaller clients that can’t afford a video editor, but they have someone on staff who can use the video, um, AI tools.

And it’s pretty inexpensive. And again, it’s democratizing, making great content across any brand, big or small. Um, I just think that’s going to continue to get better. Um, I think more.  Versions of creative that are more contextual, being able to put them in, you know, we talked about retail networks and segmentation and being able to serve kind of the right kind of creative to your audience, I think, continues to still be important.

And, um, and I feel like if you’re not doing that today, then you’re not doing something right. Um, so yeah, I would say that looking in the crystal ball, I just, I think that the marketplace is going to drive hard to just. Continue to make those tools better, uh, to, to make great creative. And, um, yeah, I can’t wait.

We gotta, we’re going to meet another year and a half and we gotta be like, okay, what were we doing a year and a half ago? It’s a great point in time when there’s just so much technology.  I was talking to a friend, we were going to dinner and she’s like, yeah, I’m thinking about putting her kid in a coding class.

And I was like, kids aren’t going to need a code. Our kids are  not going to need a coach. She’s like, what do you mean? I’m like, AI is going to code for you. And she’s like, no, she’s kind of laughing at me. And then today I send her a link to claw, just launch their code. You know, they’re coding. I was like, see, told you.

And I was like, this technology is changing so quickly right now. And it’s just amazing to see what, you know, our roles in life are going to turn into. And then as our kids get older and as these college aged kids get older, what are their jobs going to be? Like, what are jobs going to look like in the future?

Um, with just this so much like rich technology that’s going to just really advance, um,  you know, kind of everything that we’re doing. So,  but yeah, I’m, I’m, I’m. I like it. I’m a, I’m a techie. So it’s, it’s, it’s exciting for me and I try to learn everything I can about everything coming out. So it’s great. So here’s a scary statistic.

So, you know, Gen Alpha just entered the workforce this year. This is their big year to enter the workforce. Gen Alpha, they will be work. So the jobs they get  65 percent of the jobs that Gen Alpha are going to be working in do not exist today.  Wow.  That is true.  I mean, I believe it. I think, um, you know, for some of your younger viewers, I feel like if you’re kind of in maybe your 22 to 26 range, 27, 27.

You’re maybe in a little bit of a lost generation and that generation behind you might leave frog you because they have all this AI experience. And so my advice, and I mentor a lot of people across all of my clients in this age range, and I’m like, you need to learn this stuff. You should be better at it than me.

Why am I training you go learn something new and you come train me. Um, and I think that, you know, I think that it’s just going to be so important. Um, to, you know, to be successful as that generation kind of grows in their career because  they’re not going to get those 60 percent new jobs. It’s going to be these kids coming out.

They’re almost going to create their own jobs. So that’s a great,  yeah. I love that.  Lindsay, it’s always a pleasure having you on. Here’s what I’m going to tell you. I’m not going to wait a year and a half to have you back. So you’re going to have to come back in a shorter amount of time.  Love it. Love it.

Anytime.  Thank you. Thank you so much.  Thank you for listening to Retail Unwrapped. We’ll be back in one week with another podcast. Please subscribe on Apple Podcasts, Spotify, or any podcast. If you have questions, ideas for a podcast, or anything else, please contact us via therobinreports. com.

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