From Sneakers to AI Retail Leadership with Jenna Posner!

AI is transforming retail at an unprecedented pace, and in this episode of Retail Leadership with Steve Worthy, we explore what leaders need to know now. 

From sneaker culture to digital transformation, Jenna Flatman Posner shares how her background as an elite athlete shaped her approach to leadership, strategy, and innovation. 

We break down AI’s real impact in retail—cutting through the hype to reveal practical applications, branding challenges, and the evolving balance between human expertise and automation. Discover how AI is reshaping customer experiences, store operations, and leadership strategies, and why executives who fail to adapt risk falling behind. Whether you’re navigating AI adoption or rethinking retail’s future, this episode delivers bold insights and actionable takeaways to help you lead with confidence.

CHAPTERS:
00:00 - Intro
01:18 - Jenna Flatman Posner, Chief Digital Officer
02:55 - Sneakerhead Culture
09:03 - Early Sports Career and Olympics Journey
10:57 - Personal Athletic Journey
17:34 - Transitioning from Athlete to Entrepreneur
20:25 - Importance of AI in Today's World
21:10 - AI Applications in Retail
24:07 - AI Branding Challenges
27:17 - Human vs. AI Work Dynamics
30:31 - Future of AI Technology
34:04 - Future of Retail Trends
39:18 - Steve's Vision for AI Future
39:45 - Retail Leadership Strategies
42:20 - Retail AI Council Initiatives

Transcript

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SPEAKER_03 0:00

When I first heard today's guests, we were at this conference and I was sitting in the front row. And I gotta tell you, when she was speaking about AI and and retail and leadership and what people are getting right and what people are getting wrong, I I couldn't help but to agree with the vast majority of everything that she was saying. And right then and there, I knew that I was gonna have to have her on this podcast. We're gonna be talking about a whole bunch of things. We're gonna be talking about AI, uh, we're gonna be talking about leadership, we're gonna be talking about her journey um uh as an athlete, but we're also gonna be talking about we're both sneakerheads. So I'm super excited uh for you to listen to this conversation with Jenna Posen. She is the founder of Chief Digital Agency and also the co-founder of Retail AI Council, of which I happen to be a member of, which is really cool. So hold on, get ready. This is gonna be an amazing episode of Retail Leadership with Steve Worthy.

SPEAKER_01 1:02

Welcome to Retail Leadership with Steve Worthy, where we go well beyond the corporate playbook to unpack major opportunities, hidden challenges, and critical issues that senior retail leaders face every day. If you're ready to get the insights you need to elevate the impact you have on your team, increase the profitability of your stores, and level up your retail career, then keep listening, my friend, because I see a lot more success in your future. So let's get started right now.

SPEAKER_00 1:40

Super pumped to be here today. My name is Jenna Flaytman Posner, uh former retail tech executive, former retail executive, and uh most recently entrepreneur. Uh just started an agency called Chief Digital Agency. Spirit of that agency is to sit at the intersection of how technology is built and brought to market and how it is bought and implemented on the retail side. So sitting squarely, right in the middle, uh, and that friction point between technologists and retailers, helping them smooth it out and deliver more tech and more value. So um, yeah, my my career kind of uh first half of my career was on the tech side, second half on the retail side, serving as CDO for a couple decent sized brands. Um, but I really feel like I'm using my powers for good now and uh trying to spread them across the industry. So it's a pretty fun time.

SPEAKER_03 2:29

That's good. That's good. I I'm gonna so we're gonna start with a very, very non-AI question. And um I I've I think I saw I was actually at Retail Fests probably maybe a year or two ago or something like that. I think you spoke at Retail Fests on San Diego, and I I noticed, I noticed that. Are you a sneakerhead? Oh, yeah. Yeah. So that I gravitated to that. Like I saw there was a picture actually of you holding a whole bunch of different sneakers. And and so and so I was like, you know what? I'm not gonna start with uh AI real quick because I'm a sneakerhead. And um how how did that happen? Like, have you always been a sneakerhead? Like, what where did that happen?

SPEAKER_00 3:12

Yeah, it's kind of funny, and this this actually leads to like a a pretty funny childhood story. So I was always an athlete, right? I I played on the USA rugby team for seven years. Um prior to that, I was a collegiate athlete. I was a runner, field hockey player. Um in high school, I was a runner and an ice hockey player. Um, so you know, I've been an athlete for a long time. I've been wearing Nikes for a long time. And so, you know, and I think what's so interesting, as we get sadly older, what we find is that these silhouettes continue to just come back and come back. And there's this like beautifully nostalgic respect that sits with these shoes, um, not to mention the tiebacks and colorways and you know, all the history and stories that these shoes tell that are so fascinating. But I was always so obsessed with Nike. I was always in Nike shoes.

SPEAKER_05 3:58

Yeah.

SPEAKER_00 3:59

Um, ever since I as far back as I can remember. And in fact, when I was a little kid, when I was like seven or eight years old, if you asked me, Jenna, what do you want to be when you grow up? Most kids would be like, I want to be a firefighter, I want to be an astronaut. I would say, I want to run advertising at Nike.

unknown 4:16

Wow.

SPEAKER_05 4:16

That's what I would. Yeah. Wow.

SPEAKER_00 4:18

So if you went to my eight, nine, 10-year-old bedroom and even into like into middle school and even into high school, my walls, looking back on this now, I'm like, how did it, how did it take me so long to get here? But you look at my walls, you'd see it plastered with Nike ads. I'd rip them, tear them out of magazines, Nike ads, absolute ads. I thought they were so witty and fascinating and artistic. I would save Ben and Jerry's containers because I thought they were so funny. I would clean them out and pin them to my walls. I had CPG all over my walls as a kid. That's awesome. Like looking at it now, and it's so funny, even seeing it trickle into my life now. My kids are also obsessed with CPG. Like they're obsessed with brands. They have like Doritos and Takis, t-shirts, and sweatshirts. They have prime stuffies and like ramen pillows. And I mean, it's just it's, I don't know. It's ingrained. It's ingrained. Not respect for brands. So Yeah.

SPEAKER_03 5:19

What's your favorite? What's okay? What's your what's your favorite? What's your go-to pair? I know you got a whole bunch of those.

SPEAKER_00 5:25

You know, there's a I I've got this fearless pair that's got this, these like gold watches on the toes.

SPEAKER_05 5:30

Oh.

SPEAKER_00 5:30

Um and it says, oh, I'll probably butcher it, but um, around the soul, it says, if you knew what you had was rare, you'd never lose it, or you'd never take it for granted. Something like that. It's like, if you knew what you had was rare, you'd never lose it. I don't know. I should go get them. Hold on, I'm gonna get them. One second.

SPEAKER_03 5:48

I want to see them. I want to see them. I want to see them.

SPEAKER_00 5:50

All right, you ready for these advocacies?

SPEAKER_03 5:52

Oh, yeah, I want to see it. Yeah, yeah, yeah. Come on.

SPEAKER_00 5:55

If you knew what you had was rare, oh you'd never waste it. Oh, so much better. And look at this one, look at this one. Oh my god, it's a different color. Oh man. That's my favorite.

SPEAKER_03 6:16

Yeah, that's awesome.

SPEAKER_00 6:18

You know, so I've been I've been into sneakers for a long time, and what was so interesting about my retail journey is that when I got recruited for my first retail gig, it was with Snipes.

SPEAKER_05 6:33

Okay.

SPEAKER_00 6:34

So, you know, yeah, so Snipes is the global sneaker and streetwear retailer.

SPEAKER_05 6:38

Yep.

SPEAKER_00 6:38

And I thought, oh man, if I'm gonna do this thing, if I'm gonna go on the retail side, this is it. I I can't be more passionate about the product than I am. And so if I'm gonna do it, it's it's gotta be with Snipes. So and it was it was an epic start to my uh my formal retail.

SPEAKER_03 6:53

That's awesome. That's awesome. There's there's so many, there's so many stories um, you know, in that, in that journey as a as a kid. So my I'll just a quick quick sneaker story. So, you know, my my cousin, I don't know, maybe two, three areas removed, or not generations, but two, whatever you call it, removed of James Worthy. Um, right? I didn't I don't have any of his height or any or any of James Worthy's heights, right? So he used to play for the Lakers. And I remember, you know, uh and in high school, I played, you know, played a lot of basketball and baseball. And I won, he came out with these sneakers. He came out with these like new balance sneakers, and I was like, oh man, I want them, I want them, I want them so bad. Um and I'm the youngest of seven. I'm the youngest of seven, so I was always a little spoiled. Yeah, I was always a little spoiled. So, you know, my mom and dad used to always like, if they didn't get it for me, my siblings would would always get it for me. So so I I I my first like pair of like sneaker sneakers were those. And it was a James Worthy New Balance. My sister Kathy came home one day, and and um, I came home from school, and actually about two weeks prior to that, her and I had a like an argument or whatever, and she she said, here you go, like in a very like attitude, but here you go, take these. And I'm like, What what do you what what what is what are these? What are these? And I opened a I opened a box and there's freaking the James Worthy like new ballast sneakers. I start crying. I literally start I literally start crying, I literally start crying. That started my sort of sneaker addiction, you know, that first that first pair, you know, of shoes, which is crazy, which is crazy. So I know I wanted to have that conversation with you because I I saw all those all those images of you with with with sneakers and everything. So the the interesting part, right? So you said, you know, little Jenna, right? You know, was this like I want to work from I want to work for uh for Nike and I want I want to do marketing, right? And then you did a whole bunch of sports. Walk me through that path to like where you are today, right? Because you just did a whole bunch, you know, you did a whole bunch of you're doing a whole bunch of stuff right now.

SPEAKER_00 8:58

Yeah, sure. Um you want the career path, the sports path, you want to see where they intersect? What do you think?

SPEAKER_03 9:03

I want the sports path. You know what? I want the sports path. I want the sports path because we're gonna get into the AI stuff in a second. We're gonna get to the AI stuff in a second. Because I think this tells the story.

SPEAKER_00 9:14

Sports path um began at age three. Uh gymnastics.

SPEAKER_03 9:22

Okay.

SPEAKER_00 9:23

Uh my father would put me to sleep and would say, Good night, Jenna. I love you. Olympics. Oh yeah. Oh yeah.

unknown 9:32

Oh yeah.

SPEAKER_00 9:33

The pressure. The pressure was uh laid on pretty thick pretty early. And I think what was so interesting and empowering about that is like it was just like expected that that's something that was within reach for me.

SPEAKER_03 9:48

Yeah, yeah.

SPEAKER_00 9:49

And it I never questioned it. I just believed that that was the path I was on.

SPEAKER_03 9:56

Yeah.

SPEAKER_00 9:56

Right. So like the power of that confidence and the lack of fear associated with the with the expectation, you know, I think is just I don't know, it was a very I I look back on it now and I'm like, was that pressure? Was it inspiration? Was it expectation? Was it just my baseline? Right. But I think that my father with that he gave me something in that. Yeah. Not just pressure, but some some something else that like there was no ceiling. It was just, it was always there. It was always something I could do.

SPEAKER_03 10:30

Yeah.

SPEAKER_00 10:30

Does that make sense?

SPEAKER_03 10:31

No, oh hundred percent. 100%.

SPEAKER_00 10:35

So it started that young. Um, three, four, I was uh gymnast. I was on ice skates. It's kind of that's kind of how it started. Um and I did that until I was about, um, and that was me competing, you know, being comp being competitive, um until I was about uh 11. We moved to Vermont. You know, my parents every weekend we would like, I grew up in Rhode Island. So my parents every weekend we would go up to Vermont to see friends. And and the way they describe it is like my cheeks were always pink in Vermont.

SPEAKER_05 11:08

Yeah.

SPEAKER_00 11:09

Right? Like I was always outside, I was always running around, I was always like having a blast. And they just wanted that for me all the time. And so they decided, like, we're going up here every weekend, let's let's just move. And so we moved up to Vermont when I was 11. And that's when I was really able to lean in to athletics because it was just a part of the culture there. It wasn't like I was in this in Providence, I wasn't in this city trying to find a way to be an athlete, you know, in this like mini concrete jungle. Instead, I was in the sticks where you're defined by the activities that you, that, that, that you accomplish, that you do, that you participate in. And so I was a rink rat. I was in the rink all the time. I picked up ice hockey, I was still figure skating. I was there I was in the rink more than I was home.

SPEAKER_05 11:58

I was like, I was in the rink all the time.

SPEAKER_00 12:00

Until finally, when I was 12, I went to my dad and I said, Dad, listen, I don't want to figure skate anymore. I just want to play ice hockey. Um, to which my father started crying.

SPEAKER_03 12:12

Oh.

SPEAKER_00 12:13

Sad about it. Um, but he supported me and and so did my mom. And and that is that's when I like I leveled up. I be it became about the team, right? It wasn't just about figure skating and like doing the next jump or the next, you know. It was it it my mindset changed into a team mindset at that point. And I learned what it meant to be a part of something greater. So I was a goaltender for about a decade. I was a goalie. Um absolutely loved it.

SPEAKER_03 12:42

Um what's up? That's a tough position. I played a little high.

SPEAKER_00 12:50

I loved the pressure though.

SPEAKER_03 12:51

Yeah.

SPEAKER_00 12:52

Loved it. Um and uh and I played, I played at pretty high levels. You know, I I did like Vermont All-Stars and Junior Olympics and went to hockey night in Boston and like, you know, did all the kind of like recruiting activities that one would do. Um went up to Canada for camps and did all sorts of, you know, I was like in it. I was like really in it. Um and then I started going to uh Dartmouth Elite Hockey Camp. And this is where everything shifted for me. I realized that all of the athletes, all the all the girl athletes that were really competitive there went to prep school. And I came back after one summer of camp and I said, Mom, dad, if I'm gonna be an athlete, I gotta go to prep school. And they were like, Okay, yeah, sure. Like, we did not come from money, right? I did not come from money. They were like, here's the deal. You do your research, you apply, and if you get in, we'll talk about how we might be able to get you there. So I got my parents to take me on a couple tours. Um, I called up hockey coaches, I convinced them to come watch me play. I mean, I'm like calling 1-800, you know, Exeter and 1-800, you know, Andover, and you know, just hey, can I talk to someone in the athletic department? You know, like as a 14-year-old. Uh and I uh I toured a bunch of places, got in a bunch of places, and ended up really feeling at home at Northfield Mount Herman. So I went to NMH and Western Mass. And um, and it was the best decision I ever made. Um I went to boarding school.

SPEAKER_05 14:26

Yeah.

SPEAKER_00 14:26

I became more independent. I got that really aggressive play and I discovered track and field and um realized that all of the assets that I had on the field or on the ice, whether I was playing field hockey or ice hockey, it was all about pace and speed and quickness. And being able to harness that on the track was a really big, um, a really big shift for me and my athletic career. So I became a runner. I ended up getting recruited to run all over the place. Um, I ended up choosing my education over my athletic career. Uh, I selected Wesleyan in Connecticut, uh-uh. Uh division three, but had lots of fun. I was a three-sport athlete. I played field hockey in the fall, which gave me a nice, you know, core foundation for my indoor and outdoor season. My uh track coach hated it because it's a brutal sport. Swinging sticks and running. It's like crazy.

SPEAKER_03 15:19

Don't get hurt. Don't get hurt. Yeah.

SPEAKER_00 15:21

Yep. Uh, but uh, I was an indoor 55 and 200 meter runner and an outdoor 100, 200 meter runner. Um I was a seven-time All-American, uh, won a national championship my junior year in the 55 meter dash.

SPEAKER_03 15:37

Wow.

SPEAKER_00 15:38

Yeah, it was it was a pretty cool, pretty cool time. So so that was my running, right? Um, and then my uh senior fall, I missed my fall field hockey season, went abroad to Australia in 2003 and discovered rugby. And uh I was there during a World Cup year, didn't know the gift I was being given, saw all of this amazing play and was like, this sport's nuts. I love it.

SPEAKER_05 16:02

Yeah.

SPEAKER_00 16:02

So I came home, I ran my indoor season. I think I placed fourth. I was like fat on like beer and fish and chips, you know, for four months in Australia. It's like it was no business running. Uh, but I did. I ran my indoor season, and then my outdoor season, I was like, you know what? I've accomplished my goals. I want to try this rugby thing. And uh yeah, so I played rugby my senior spring. A friend of mine wanted a tryout to a regional tryout. I was like, well, if I'm gonna take it, I'll I'll try out. I made the team. A month later, I was at a national championship, got scouted by the US under-23 team, and like three weeks after that, I graduated and was on a plane to Canada to go play for the under-23 team. And then uh I was in a in the pool for seven years. Um my focus was sevens, which is the rugby that's played in the Olympics today.

SPEAKER_05 16:47

Yep, yeah, yeah.

SPEAKER_00 16:49

Um and it was it was a blast. It was a blast. Uh lived in New York City after college, played for the the New York women's rugby club, won like, I don't know, five national championships out of the seven years we were there, and then I got married, moved to Philly, and hung up my spikes.

SPEAKER_03 17:08

And that was it. That wasn't but that but but that wasn't it, right? I mean, now your your your story shifted, right? It's it, you know, you went from, you know, you know, five-star athlete to now, guess what? You know, now I I want to do something different. How did what where did that shift take place? And like what made you move to what was next?

SPEAKER_00 17:32

Yeah, I think what you're what you're getting at, well, well well, I'll tell you like the the tangible shift that took place, but I also know what you're getting at, which is like that athlete mindset doesn't go away just because you're not competing, right?

SPEAKER_03 17:41

Oh no, we're gonna talk about that yet.

SPEAKER_00 17:42

Yeah, it's still there. P.S. I play pickleball like two days a week, so I'm still in it to win it over here. But anyway, so um I sat down with a US coach and we knew that uh rugby was gonna be added to the Olympics. Mm-hmm and was starting a four-year cycle. And we sat down and we had a conversation, and he was like, You could do this, you could do this, but it's gonna be a risk. He's like, I am going after uh high school kids right now, you know, kids that are 15, 16. Um, that's who I'm gonna be recruiting now, and I'm gonna develop them over the next four years. You could be that that old, that old respected player. You could be, but there's probably gonna be like one or two spots on the team for that level, for that age, for that experience. And the chances of me being that in the pool that I was in, I had a shot. I could go for it. Or I could choose to double down on my career and really start focusing on what that's gonna look like. And ultimately, that's what I chose. I chose to get married, I chose to move out of New York, and I choose to refocus my energy on uh on myself instead of my team, um, and my family instead of my team. And um, you know, had a bunch of kids and bought a house and, you know, did the whole Philly thing. So, um, but to your point about like that athlete mindset, that uh that grit, that resilience, that problem solving, that flexibility, you know, the ability to like be nimble and you know, it none of that goes away. You take that into into whatever it is that you're building or whatever it is that you're navigating or um so every day, I mean, like if if you saw me after a great meeting or in my house by myself, I'm consulting, right? I'm in my house by myself. If you saw me a call in a great meeting, you would see me like jumping around the house, fist pumping in the air, being like, let's go by myself. Okay, like that is that is like so that like that athlete mindset, like it just doesn't, yeah, doesn't go away. It it becomes a a very core part of you for sure.

SPEAKER_03 19:56

Yeah, that's good. That's good. I was I'm so I thank you for sharing that because I I wanna I want to shift into, of course, the the the topic of the day, AI, right? And and and and what and what you do. You know, you were we were at the we were at the endless aisle conference uh together, right? And you're and you're up on stage and you're talking, and I'm sitting there, and I I think you probably heard me like just sort of like almost a man, you know, like you know, with everything you said. And you're like, you're like good, you Steve, you good? And I was like, I'm like, I'm 100% there. I'm like, I am following you. I love what you're saying, I'm tracking with you. Because I, you know, I'm I'm from New York, so we you know talk on my hands, and I say if something something I like, I'm like, that's that's what I'm talking about. There you go, right? And um I and and so but one of the things that you know you you did, and you talked about AI sort of just in in in in really glowing tur terms, right? And I think in the retail space, you know, there's still a lot of work to do, right? With not just adoption, but understanding what AI's impact is going to be in the marketplace. How are you helping shift that mindset right now within retail?

SPEAKER_02 21:09

You're listening to retail leadership with Steve Worthy.

SPEAKER_00 21:14

Yeah, it's a great question. And I think it's um, oh man, it's a really relevant one because what I'm finding is my education on AI is moving so fast because I'm spending so much time in it, right? I'm a co-founder of the Retail AI Council. You know, it's a council that is like our charter is to be a retail ed organization to help cut through all the clutter and really define and identify what are the AI use cases and technologies out there that are really moving the needle. Right. So I'm at the forefront, I'm in the thick of it. But what I'm realizing as I'm translating those learnings into retailers on the consulting side is that many of them are still very nascent. And so trying to get a grasp on understanding where they are in their AI journey, where are they? They they in their trust levels with AI, where does their vision line up with the vision of the market? And like, do those two things intersect? It's everybody's really at a different place. And so what I'm finding is, well, I'm really bullish on some of these technologies and just want to jam them into some of these brands. I'm realizing that the change management process needs to really be cared for before some of those decisions can happen. I think you can get a couple quick wins here and there, right? If it's like a low cost of entry or no cost of entry scenario where you can kind of test and learn and prove the value of these use cases, that's one thing, but those are few and far between. So I find myself focusing more on how do I help these brands come to terms with really where they are in their process of adopting and believing in and championing and measuring AI so that they can all get aligned. One really good process that I put in place is just through a very standard architectural review. There are a lot of pieces of technology that brands have in place today that are leveraging AI use cases already, and they just don't know. So there's a really great and relatively easy process of just auditing the tech stack and saying, hey, let's do a workshop and say, you know, here are the 30 pieces of technology that you're using. 15 of them are already utilizing AI, and this is how. And so that education really goes a long way from a change management standpoint because it goes from the should we invest in AI to, oh my God, we're already investing in AI. And so it's it's like the band-aid gets ripped off and the conversation gets a lot uh people get a lot more receptive because it's not a yes, no anymore. It's a how.

SPEAKER_03 23:42

Yeah. Do you think do you think AI has a branding issue? You know, because I I I often think about it when you use the word trust, you use the word trust earlier, but um I was I was talking to someone else about it and and I and I posed that same question to them. So I'm gonna let you answer that question.

SPEAKER_00 24:00

I think that um I think we've been burned, right? We've been burned with the metaverse, we've been burned with NFTs, right? We've been burned with these wide-sweeping categories of technology that are on the forefront of innovation, right? Um, and I'll put that in quotes, forefront of innovation. And so I think there is a lot of mistrust in is this just another fad? Right. I think that's one piece of it. Is this just gonna like bubble up and you know, and then calm down and we're not gonna talk about it again? Um, I think that's one piece that's kind of holding us back from a branding perspective. And then the other is there isn't a lot of definition around it. And so sometimes people are really inspired by the, the, the, the width and depth of the category. And then sometimes people are totally immobilized by it because they just don't know where to begin. So I think you're right. I don't know if it's a branding issue as much as um an identity complex. Like who, who, who is it? Like who are we? Like, how do you begin? And so the result has been, and this is my opinion, I've been waiting for technology to get involved.

unknown 25:05

Right.

SPEAKER_00 25:05

ChatGPT kind of democratized the access to AI and our ability to test it and understand it and see its outputs. And then we had to wait a while. We have to wait for tech to kind of build these productized use cases so that we can actually put it into a bucket and say, this AI application is in this category and therefore subject to this budget, right? But man, as I'm looking at agentic AI, and it's it's still it's just on simmer right now. It's not quite out in market right now. Agentic AI is basically the ability to use AI agents to do anything you can do on a computer, right? So the the use case there, I mean, think about having an agent that is like working 24-7 and can't quit. Like that's pretty cool. Um, so I I think we all have to just keep going. We have to keep listening, we have to keep testing, we have to keep learning, and we have to keep building our confidence in the technology because it's here and it's coming. And the retailers that embrace it are the ones that are gonna win, and the ones that don't are gonna be left behind, in my opinion.

SPEAKER_03 26:08

Yeah, no, I I agree. I was listening to um uh uh Sinead uh Bouvelle. Um she's based out in Canada. She does a lot with AI, and she she talked about the idea around these dynamic jobs, where the the idea is that you know AI is, of course, it's a the the the the outputs are are are gonna be what's important, you know, you know, relative to what you put in there. But as a from a job standpoint, your job, think about it with agents, your job is not going to be the doing anymore, it's gonna be more strategic based on those outcomes. So now as a as a professional, as a retail leader, your mindset is not gonna be around doing. It's like, how do you strategize a little bit differently? Are you are you seeing that as a gap now? Uh that's a loaded question, right? It looks like it's a loaded question. Oh, yeah. So go go go ahead and answer. I'm gonna look for you.

SPEAKER_00 27:03

Yeah. Thanks for the softball. Um, yeah, I mean, it's look, there are all these menial tasks that so many of us do every single day, right? And some more than others, some on the operations side that are doing exports and imports and just things that don't require any solutioning or creative thought or problem solving, or it and it's just we don't need to be spending our time doing those things anymore. Right. And so from an operations perspective, deploying these, these, these bots, these agents to do that work is gonna free us up and give us more time to do the things that the human brain is really good at, right? Thinking, forward thinking, vision, strategy, problem solving, creative thought. I mean, these these machines are not creative yet. They're not creative. So my thought is, you know, how do we really work from a process perspective to identify those menial tasks, deploy these agents to complete them on our behalf to free us up to be more effective and more efficient, right? And drive more innovation, drive more strategy. I see things coming that we didn't have time to see coming. Uh it's it's gonna speed up our industry so much, and it's gonna make us so much more efficient and ideally more profitable. I I just I can't wait. I can't wait.

SPEAKER_03 28:25

Yeah. All right. So I'm gonna be the wet blanket, I'm gonna, I gotta, I'm gonna do the wet blanket thing. So where's the l, where's the line? Right. Because I I'm I am I am pro AI. I don't know if that's saying or anything anymore. But um a hundred percent, like I I understand it, I I see where it's going, but you know, where's the line? You know, I you know, there's there there has to be a line between um the reliance on AI and also like sort of the human condition and the human, the human aspects of job and work. Like where's where's that, where's that line?

SPEAKER_00 28:59

Yeah, it's a good question. I don't think it's the reliance on AI. I think I think we're still in the utilization of AI piece, right? I don't think we've fully figured out how to utilize it to our greatest advantage. And that's where I think the potential lives. Where the line is, you know, it's a great question. You know, I I think when we're talking about retail, we're about to, we are like on the precipice of a massive revolution. Like it is going to change dramatically over the next five to ten years. We've already seen it change dramatically. The pandemic accelerated so much of this adoption from a digital perspective, but people still come in stores, right? So it's I I don't think that the um the onus on the brand to be customer experience obsessed is going to change. I think that the expectation of the consumer is going to change, right? So the customer's desired experience is going to change, and the onus is on brands to meet those expectations.

SPEAKER_03 30:04

So, for example, we would say, yeah, go deeper into that one.

SPEAKER_00 30:08

We we want things to be easier. I I mean, I don't know, maybe some people love the TJ Maxx experience, right? Or the Ross experience where you gotta go in and like dig for the gold, you know? I don't like that. I I I just want gold to be delivered to my front door, right? I don't like I need efficient, I need easy, and I'm willing to pay a premium for that. And so what I believe is coming, what I believe is going to happen is that we are going to be more and more agent-led the more time goes on and the smarter these agents get, the more focused these brands become on organizing and making their data accessible to these agents, the more targeted we're gonna be. I don't want to get ads with Spanish on my TV anymore. I don't speak Spanish. They should know I don't speak Spanish. Don't serve me a Spanish ad, right? Um there's just there's a level of personalization that I am demanding that this data has the ability to deliver through the lens of AI utilization. And I don't think that those demands and those expectations are going to lessen. I think they're going to become more and more acute and more aggressive as time goes on. And so, again, those those brands that that harness their data and leverage it to create those unique experiences for me that deliver the gold to my device are the ones that are going to earn my wallet share. And my prediction is that through this lens of AI, we're going to become very, very device-led. You've got these incredibly intelligent phones that are in our pockets. You've got Apple intelligence that's out in the market. You've got an agent on your phone. You've got Siri sitting on everybody's phones, waiting to get more, more and more effective, waiting to get better. She still sucks, in my opinion. I keep testing her and she just continuously fails. But at some point, that technology is going to get activated. And I believe that the browser is going to get challenged. I believe that the search engine is going to get challenged. I believe that the standard hierarchy of a website is going to get challenged. And I think the one thing that you really will be able to continue to maintain is the experience in the physical retail location. And that is going to continue to raise the bar for how these devices need to engage with us. And so the way that this works today is I walk into a store and I get the most personalized experience ever because I have a human that I can interact with that cares about my information. They ask for my data when I walk in. And I say I'm Jenna and I'm here because I'm buying X, Y, or Z. And here's my size and my color preference, and here's the brand that I want. And that store associate takes all of that information, context about what I'm wearing it for, what I want, my size, my color, and they go into the stock room and they go find it for me.

SPEAKER_05 33:04

Right.

SPEAKER_00 33:04

These devices aren't going to be any different than that. The biggest difference is they're going to ideally be able to capture my data across a multitude of touch points, not just when I walk in the door, but they're going to understand what are my brand preferences, what's my average order value, what's my wallet size, when do I get paid? Like, how do I, like, how do we leverage all this information from Jenna to determine what she's more likely to buy right now or what she actually wants right now. And so I'm I'm waiting for that evolution. That's it, that, in my opinion, is what's uh the the potential of what could be coming.

SPEAKER_03 33:38

Yeah. And but you you actually took it a step further at the conference, right? When you you you actually brought up the suggestion of a of a um uh a team memberless store. Do you remember talking right? And I thought, and did you did you did you hear the crowd when you said that? Did you feel the tension? Yeah, like you like, it's like all the air in the room was like sucked out.

SPEAKER_02 34:02

You're listening to retail leadership with Steve Worthy.

SPEAKER_03 34:07

But I was like, I can I can see it happening. I can see it happening. Could you could you talk a little bit about that? Because I want I want the the crowd, the the audience to hear this as well.

SPEAKER_00 34:16

So here was my point. My point was that in the same way that we're rethinking what AI is gonna do to digital and the way the consumers are going to engage with digital product, we need to be thinking about the store. And so the use case that I actually put out there, the idea wasn't we're gonna replace every store associate. That's not what that was. What it was was if we look at AI and we look at the potential of what AI can offer, how do we rethink the purpose of the store and the structure of the store? And so my recommendation was today we have hours, we have store hours, right? Digital doesn't have a store hours. We're open 24-7, right? We're taking orders 24-7. So if we have the ability to infuse digital into these retail environments, how can we rethink how the store operates? So my suggestion was in those off hours, how do we leverage technology to have a contactless store where a consumer can actually earn the right to let themselves in to a store that is, quote, closed and self-checkout, right? If I want to order something for same-day delivery at midnight, could that get routed to Uber Eats? Uber goes and picks up my item from the store that's nearest the consumer and brings it. Can we have same hour delivery? I mean, like there's there are new ways that we can start thinking about this through the utilization of technology, devices, and AI that we just haven't in the past. And so there is technology out there now where I can pre-auth a card on my phone and that pre-authorization can actually unlock a door. So let's say it's eight o'clock at night and I'm walking down the street and I see a bag in the window that I want to go buy. In theory, I can pre-off my my card for 400 bucks. The store will know it'll let me in and I will go scan that bag and check out. There's, you know, there's security everywhere, there's cameras, right? You're known because you're we've just offed your card. Right? There's fraud layers and making sure we know it's you, right? There's device IDs and there's all sorts of precautions that we're taking to know that this is actually Jenna. And I can come in and I can, I can buy and take that bag and leave in the store locks behind me. So I brought it up not to polarize the room, but I brought it up to help expand the concept of what the store could be to the consumer and ways to leverage digital to continue to amplify the digital voice of those physical stores.

SPEAKER_03 36:44

Yeah. I it's funny. I remember um when Panera uh years ago, when they had the first, you know, um, your ability to actually pick up in store. Um, and I and I felt so uncomfortable going into that physical. I've already already paid online, but they had they had the meal in the little box, right? Steve Worthy, and I walk in, and I'm like, I'm like, you know, I'm I'm here. It's I'm Steve. This is mine. This is this I swear this is mine. I'm walking, I'm walking, I'm walking out here. And it was such an uncomfortable experience. Um, and I and I I had a whole bunch of other people, you know, um share their same experience for me. I can almost now you're now you're talking about, you know, leapfrog maybe, I don't know how many years ago, maybe 15, 20 years ago. Right now there's such a level of of comfort, you know, with you know, with with with with that type of scenario and with the situation. And I don't feel like we're too far off from the scenario that you're talking about at all. Trevor Burrus, Jr.

SPEAKER_00 37:50

Doesn't it feel like a natural progression? I mean, it really I really don't think we're that far from it. In fact, the technology exists, it's in market, so it's coming.

SPEAKER_03 37:59

Well, we we see we we see with Amazon Amazon Go, right? Their stores, right? You know, where you can you walk in the store and you just walk out, right? I mean, you know, that's a that's a that's a you know scaled down version of that or whatever, but it's it it's still the same principle applies to what they're actually.

SPEAKER_00 38:14

I mean, they're a little bit more advanced in that you don't actually have to scan anything, which is kind of cool.

SPEAKER_03 38:19

Aaron Powell Oh, a hundred Exactly.

SPEAKER_00 38:21

We were in the UK this summer, and um uh me, my wife, and my three kids, and we brought them to an Amazon Go store and let them just go nuts on candy, and they like and then we just kind of walked out and they were like, what's going on? And we were like, oh no, we're just this is all free. It's all free candy. And they're like, What? Can we go back? And I was like, it's not free. It's just and I explained the whole situation. They're like, their minds were blown. They were like, wait, what? You use your palm to leave? Like, what's happening?

SPEAKER_03 38:47

It's like, what is what is what kind of magic is this, mom? What are you doing? All right, I would I want to close with um a couple of things for for 2025. I you've been in several meetings before. You're you're an exec, you run all these different businesses. You've been in a start, stop, and continue, you know, meeting, right? So I I want to get your best like start, stop, and continue for for for 2025 for for for retail brands and even retail leaders.

SPEAKER_00 39:16

Start, stop, and continue. Oh, um, oh God. Um I would say, I mean, can I keep it AI focused?

SPEAKER_03 39:28

Yeah, yeah, 100%. Go for it. Go for it. This is your show. This is your show. You can say whatever you want to say.

SPEAKER_00 39:36

I would say um start well, let's go stop first. Like stop challenging these AI use cases because you're afraid. Like just find real reasons to challenge these AI use cases, right? Like don't put up barriers because you're concerned about the unknown, right? And and I would say start really leaning in and testing and educating yourself because if you're not doing it, um you're gonna you're gonna be left behind. You know, I'm I'm I'm down this you know, board of directors path, you know, with a a number of um I'll call them agencies that place board members, right? Um and the need, the need for an understanding of AI right now at the board level across the public sector is through the roof. So if you are not reading, absorbing, testing and learning, it it's gonna catch up with you really quickly. So I I just think from an executive standpoint, we need to start testing more. We need to stop putting up phantom roadblocks, right? Because we're scared about what's coming. And we need to continue to lean in and um and and really work to quantify the value of AI in our organizations. And one major path to doing that is creating committees, cohorts internally, ownership over AI across discipline and making those leaders work together in order to come together with a perspective on what does AI mean to our business? So what is our plan? Um, because you know, digital executives have been fearlessly testing because that's what we do. But now it's time to really figure out how do you infuse this across the business. There are opportunities, it's limitless with planning, with allocation, with reallocation, with store transfers and proximity routing. And there are there is so much opportunity for efficiencies and profitability to be generated by AI that executives have just got to get on board and learn more about this.

SPEAKER_03 41:54

Good. Good. And they need to join the um the retail AI Council or something like that. I think there's an organization out there that they should.

SPEAKER_00 42:02

Certainly can't hurt. Certainly can't hurt.

SPEAKER_03 42:04

What what I what what what organization is that? I don't, I, you know, I have no clue what that is.

SPEAKER_00 42:11

Yes, the retail AI Council is a retailer-led organization. I'm a co-founder along with uh Andy Lodato, the COO of Vitamin Shop, and Doug Weich, the CEO of Safel. Um, we came together to create a committee of retailers dedicated to helping us all find our path and find our way through this AI journey. There is a lot of fluff. There is a lot of people putting AI in their name so they can be relevant, but not all of them are actually implementing AI in their technology. And so we are here to call out the BS and champion the products that do deliver.

SPEAKER_03 42:46

Excellent, excellent. Well, there will be a link to her uh organization in the in the notes for everybody. Um I knew this episode was gonna be amazing. Um I knew um I love your energy. Uh I I I love everything about you. I love your conversation. I love how you see things. And um I appreciate your boldness, right? Because I think, you know, this this this AI journey requires boldness. It requires like cutting through the fluff, right? Stop talking, you know, stop talking the buzzwords, like talk about action and how we can actually you know uh create some serious results. So, um and I'm all about results. I just really let you know I really appreciate you.

SPEAKER_00 43:26

Well, you're easy to talk to, Steve. I appreciate the time.

SPEAKER_03 43:30

Thanks for being here. Thanks for being here. All right, all right, cool.