Customer-Centric Strategies for Retail Success with Derek Yarbrough

[00:00:00] Ian Faison: Welcome to Chiefly Digital, the CDO's playbook for defining and driving the transformative shift in modern commerce. I'm Ian Faison, CEO of Caspian Studios, and today I have the pleasure of introducing the host of the show, two time CDO, three time CTO, Jay Topper of fabric. Jay, how are you? 

[00:00:25] Jay Topper: I'm doing great, Ian, and you're my first podcast, so I'm excited to See what turns out here at the back end.

[00:00:32] Ian Faison: Yeah, it's gonna be an absolute thrill. I have loved our conversations together behind the scenes, uh, until this point, and just like, between, you know, what we're gonna get into here with the, you know, Topper's 10 for a CDO, and the role of the CDO, and all those things, it's just, it's thrilling to be. Just getting to know you and chatting about all this stuff.

I appreciate that. So who the heck is Jay? 

[00:00:54] Jay Topper: Yeah, you know, I saw that question and I've struggled with how to answer it. I have several components. I look at, I break my life into three careers that I've had since high school. The first was, and we share this in common, I believe, is I joined the Army right out of high school under then President Jimmy Carter, and I was an air traffic controller.

I received an appointment, congressional appointment, to West Point. And. Super intimidated when I went up there in January and I said, well, I'm not going to do this. I'm going to go back to Fort, what was then Fort Benning and just talk to helicopters and airplanes as some punk 19 year old kid. But someone had suggested the Coast Guard Academy.

So I applied and was accepted there. And then I spent, uh, six or seven years at sea and a tour with Naval Intelligence, uh, down in Panama. And then I self funded my master's degree in telecommunications at what is now NYU, it was Brooklyn Polytechnic, and that started the second phase of my career where a third generation stage hand for a company called PRG, and he's basically invented the automation of telecommunications.

Stage movement on Broadway and became financially very successful. And he wanted to hire a CIO as part of his portfolio of new executives he was hired. So right out of the Coast Guard, I started as a CIO and that was 1997. And then I bounced around in C level employees every four or five years, Rosetta Stone through their IPO, a couple of turnarounds, FTD into and out of bankruptcy, a couple of fast growth companies, Chico's FAS, and now I'm starting my third career, which I never would have thought I would be working for a software company out of the Bay Area.

But I fell in love with this software company when I was at Chico's and immediately, you know, responded positively to an outreach from their new CEO. And so now I'm starting my third career, if you will, at 63 years old, and that's kind of who I am. 

[00:02:53] Ian Faison: It's, it's quite the story and uniquely you and that, you know, I've been just talking to you and discussing, you know, the role of the CDO and what makes this, it's truly so interesting because you've had every single part of what means to be a CDO throughout your career and all these different types of roles and now there actually is a name for it, right?

Now there is this thing called a CDO. And you've, you know, helped build this over your time being a CDO twice, and it's cool to sort of see it all come together. What do you think, what do you think is the role of the CDO right now? 

[00:03:27] Jay Topper: You know, it's a great point that you made because even if you go backwards in time to where I was CTO, they were, or CIO, they were very transformative roles.

And sometimes I was brought in. You know, in, in a transformation was underway and sometimes to help come in and define it and actually build that culture. So I think the role, the function has always been there since I've been in business and I attributed to a couple of, and now it's just starting to accelerate.

So I, we're seeing more and more of it. And this podcast alone, chiefly digital around the CDO position that it's got legs. And. Number one is I think it's transformative in nature. That's such a trite word and it drives me nuts when people talk about going through a transformation. But I actually pulled the title myself from a McKinsey document describing the role of the chief digital officer.

That was probably 10 years ago. And it was by definition a temporary and transformative role at the time that they wrote this article. And I really embrace that because I think everything's temporary in today's world. And I think it's very mission oriented that you have a defined set of goals that you're trying to achieve.

And at some point you're either have achieved those goals or you have landing assured and you're going to achieve them. And at that point, you have to relook at what the company needs. But I think there's a couple of components to it. I think number one is, in today's world, rising the tide of all the boats around you, all the different functions in a business with regards to technology and data.

Because at the end of the day, The smarter your company is around these just concepts of enabling technology and the use of data, you know, AI, but even just simple reporting to make business decisions, the smarter people are, the smarter the company becomes, and the faster they can act. I think there's a cultural shift too.

When I think of Omnichannel, I go back. And I've heard that word so long in my career that I almost attribute it to the brick and mortar way of looking at adding e commerce to the portfolio. When I think of Omnichannel and I like to use the word connected commerce, it's, there's so many billions of touch points to a consumer now on telephones and internets and chats and postcards and catalogs and websites and mobile and in store and just unlimited and.

And at every one of those touchpoint, a brand is trying to fulfill whatever promises they believe the consumer is expecting and hopefully exceed that. And that has to be done really quickly because just like when you're designing a product in fashion retail, for example, the closer you can get that design to when you can put it in front of the customer, the more valuable it is.

You can anticipate those needs. And so I think there's a real speed component to this too, and a real. Digital philosophy of being agile, of being incremental, of failing fast. And it's not about e commerce. It's just about a way of anticipating where modern retail and the modern retail consumer is going.

That's a lot of words, but I think whether you're coming from marketing or technology or operations, I think it is, it's omni across the organization of trying to raise the digital IQ of an entity. 

[00:06:45] Ian Faison: I love the idea of raising the digital IQ because that's what it feels like, right? It's like, are people embracing data?

How data driven are they? Are they embracing technology? How much are they doing that? What are the different functions that are doing it? Where do you see, like, does the CDO sit next to the CTO? Do they, you know, where do they fit in the org chart? Yeah, 

[00:07:07] Jay Topper: that's a great question. And I remember back in the early 2000s when CX started to be a big, huge term, and there started to be roles around who owns the customer experience, and a lot of times that was fragmented.

There were chief customer officers that were individual contributors. There were chief customer officers that had, you know, the customer, they actually owned the customer and the experience. I think you see the same thing with the chief digital officer right now is that different companies are approaching it differently.

Uh, the ones that are embracing the role. And in my case, in both my roles, the CIO and CTO functions were under me. And so, so I had a pretty wide purview. Uh, I also had supply chain, customer service and other areas as well. And at one company, marketing, merchandising, and basically the whole P& L. And it's one of those things that if you have that.

Much control. There's control versus influence in any organization. If you have control, you have to act like you're an influencer because these things work from a groundswell up and they work by really showing people yourself on how you're doing it. You know, good data and simple data put in front of somebody, they go, Oh, wow, my gosh, I didn't realize that was happening.

And they make a quick decision, you know, versus, you know, tabs and tabs of spreadsheets, trying to find different data. Everything is accelerated. So if, and you don't want to top down that, because in my experience, organizations that are trying not to be siloed. You really have to work across the organization.

So I think at the very least, the role has to be a peer of the CTO, a customer facing the experiences, but in some cases, technology can fit under there nicely as well. 

[00:08:50] Ian Faison: Yeah. And this is sort of, we've seen this, you know, with security and the CIO sort of in a similar way, right? Where it's like, does security sit under the CIO?

Is it? You know, is it a peer, you know, as these things change, it's like if every single thing that touches technology is one person's job, then that's a pretty big job, right? 

[00:09:08] Jay Topper: Yeah, you know, when I think back in my career, what got me into technology was I was in Panama, literally crawling around jungles with a Sony.

Camera that costs like 20, 000. And you put a, what was it? A three and a half inch floppy and you could take like four pictures. And then I was using pre internet to send the image to ships that were out at sea. And I was like, I got to go figure this stuff out. But back then technology was almost, you know, it was only 10 or 15 years away from being in the basement with punch cards for crying out loud.

Where, you know, seen and not heard. And. And it's just accelerated so much. I can't, I mean, I can't, you know, then there was the CIO role and that was very back office y. And then the CTO, hey, I'm dealing with stuff that the customer's interacting with, which I think really started more in product companies like fabric.

And now all of a sudden it's everywhere. And CIOs have to make a massive transformation to get into that CDO or even CTO role. Because it really is about the consumer and it's about ROI based investments. And you always have to make these investments that aren't, but at the end of the day, the CDO should be very dialed into the P& L and that every action is somehow stimulating a positive response with inside that P& L.

So yeah, it's changed a lot and I don't think it's going anywhere fast. With AI coming around the corner, you could have a chief AI officer before you know it. And I'm a big believer in AI and the power of computing, you know, data centers are power. You know, they're basically power companies now that happen to have computing power because they're so powerful right now.

So, so yeah, I think it's, I don't think the transformation is over. I think it's going to continue. 

[00:10:48] Ian Faison: Does every retail company, like retailer or commerce, business need a CDO? 

[00:10:56] Jay Topper: You know, it's a good question. I think that I look inside the company. When my boss hired me, I worked for the CEO of Chico's the second time I was CDO.

And she was, she and the board were both fully embracing this digital first mentality. And I led the digital first mentality. Pillar there, which again was a cultural shift more than it was anything to do with technology or data, even though those were big components. I think that if there's a true recognition that what we're doing now is not adequate and that we need to go faster and we need to get our solutions and our experiences closer to the customer, meet and exceed their expectation, because there's a whole dynamic going on now where, Hey, you know, there's the safe way.

Let's just hold what we've got and not make change. It's doing okay. Versus, Hey, let's rip it all out and redefine everything. But there's really a middle ground there. There's a place, a time and a place to swap things out, to make it easier, better, faster. And if the company recognizes that, I think they need to have a CDO or Those functions under a human being that is empowered to do that.

If they haven't embraced that, then I think less so. Then you're going to have more of an individual contributor that may be less effective. And that becomes hard. It becomes hard to sell the concept if you don't have some top level support behind it. But I'm obviously a big fan. I've personally chosen the title twice.

In neither case was the company looking for a CDO, it's just where I ended up, the position I ended up filling. 

[00:12:24] Ian Faison: Yeah, I mean, that's part of the reason why it's so interesting is because you chose that, that title for yourself. There's truly nothing else you'd rather be doing than being a CDO in that moment because of, like you said, the scope that it entails, because it includes touching the P& L, because it includes technology, because it includes data, and, and there's kind of no other way, right?

Like, that's what I think is so interesting is. It's obvious in retrospect that someone should be doing this, but you know, it wasn't always that way. But now it seems like everybody You know, should be investing in not only the CDO position, but embracing modern commerce, like embracing modern retail. 

[00:13:04] Jay Topper: You know, when I think about, you're exactly right, and you know, marketing's been there for a while, right?

Performance marketing is so much about data and personal, personalization, and I've spent a lot of time in that area. Managing it directly and serving it, but even when you get into merchandising, the traditional designing and buying of product, especially if you're vertically integrated and you're buying unique products, designing unique product, as opposed to, you know, how many batteries do I buy, but you're actually designing a bra or a pair of jeans, that the technology is infiltrating that You know, on the buying of the product, how much should I buy of each SKU, of the deployment, where do I put that SKU, I have a thousand stores, how many pairs of six, size six, girlfriend jeans do I put in the San Francisco location versus the Miami, how do I price it, and can I price it differently across regions, so Even traditional merchants that are usually, you know, responsible for the product itself and buying the product, technology is just creeping and slamming into their area as well.

So I also think you have, no matter what roots you come from, you have to really chase your weaknesses of where the company's challenges are, whether or not they're in your comfort zone or not, and you have to learn. So I think curiosity is a big component of the role as well. 

[00:14:21] Ian Faison: Yeah, you said that you made a huge emphasis on putting data at the center of everything.

As a retailer, that you felt like that was extremely important. Well, I mean, it's like, again, it's kind of obvious, but yet it doesn't, it's not necessarily what's happening. 

[00:14:34] Jay Topper: I'm, uh, I'm amazingly inept at Excel. I'll just, hey, I'm 63. You know, I, I can claim anything I want at this point in my career. And I am weak on Excel and people that, that send me, you know, big, huge 11 by 17 multi tab spreadsheets.

I look at that and I just say, there's, and you get them every day. And there's, and every large retailer. Executives there probably get 20 or 30 reports dumped on them every single day. It is impossible to navigate. I go very hands on in this regard because, and I'll build reports myself, templates for like a one pager.

Contribution margin is one of my favorite all time reports, looking at each of the marketing channels and their impact on the P& L down to the contribution margin level. And I will actually build a one pager and then I'll compare it to last year and I'll show that to people and it's, and I'll explain it to them.

And. The eye opening in simplicity, I believe in data simplicity, certainly you have to architect it smartly, and that can be complex, so you have to house it, you know, intelligently so you can get at it and do all the things you want to do, and that's a very technical exercise. But as far as the delivery of data, and I'm just talking about reporting right now, not even getting into AI, simple is usually good, and if I can understand it and my staff can understand it, and then I can get it.

People that maybe are less technically proficient to understand and go, my gosh, this is amazing. Then it can all of a sudden become a Bible of a particular area. And I've done that time and time again, where I will work with a person building the report for weeks to come up with something. I go, my gosh, this is amazing.

I can't believe the insights this is showing on our different marketing channels and where they contribute and what we're paying per customer and all this stuff, which has always been there, but it's always hard to find. And, and so I think data from a simplistic standpoint, so people can make rapid decisions.

And if those decisions don't pan out by continually measuring, back out and try something else really quickly instead of just taking months to come up with plans to try something and then months to see whether or not they, they, they bear fruit or not. So data is everything in this world. Um, and it's not.

Um, certainly in my lifetime, I don't see that changing. 

[00:16:48] Ian Faison: This past, uh, weekend was the big sale, the yearly sale at REI, an REI member. And I knew it was coming, I knew I was going to get my 20 percent off coupons, you know? I knew those were, I could use some of my, my member money, and that had all sort of planned and figured out.

And I was just thinking the whole time, like, they don't know That I'm waiting on those and that I'm going to use them, but they know when I use them, right? And there's just so much information there. There's so many things that you can do to prepare and that like, REI sending me the email saying, Hey, don't forget.

You're going to get that 20 percent full off full price item that's coming up. And I just, I think about like modern commerce and you know, this idea of you've said, it's not e commerce. It's modern commerce. This idea that, you know, I go into the store, I go try some stuff on, I go, you know, check it out. I go back home.

With my, you know, screaming toddler. And, and I'm like, all right, I'm not going, I'm not going back out to the store, but I know exactly what I want. I make that purchase online. This is so much more complex now than it used to be. It is. And it's all integrated. 

[00:18:04] Jay Topper: It is. And the data, uh, of course there's data guardrails that states and governments and countries are, are placing on retailers, uh, as well.

You have to work around those. There's all the proactive data where you reach out to a company and you do something, you call customer service, you make a purchase, you've proactively told us something, there's reactive stuff that you're not really telling us anything, but we're watching, you know, we know what pay, how many pages you went to, what marketing channel you came from, and then there's all the macro things going on, you know, Hey, who knew that dresses in Kentucky near the Kentucky Derby are going to spike, you know, That's a macro thing.

And to try to tie all these things together to give you an experience that feels special to you, you know, without being creepy, which most people embrace, you know, I want this to be, I want to feel unique, is complex. And that's only on the marketing engine. You have to get into the sales engine. You have to get into the post sale engine, which is customer service and fulfillment, and then you have to go all the way back up to the product itself.

So they can get feedback around, the merchants can get feedback around the product because for a company like REI or like Chico's or like FTD, or really all the companies I've served is it all starts with having a great product. And so what kind of feedback. on returns and you know which are coming more and more digital you hit a barcode like and all this data is coming in from all these places and then how do you use that to make the next experience better and consistent it's a lot of work and if you get everybody on board and it certainly goes a lot smoother and can be energizing and even thrilling frankly.

[00:19:39] Ian Faison: Yeah and it seems like that if you have a CDO at the top with a team who's resourced that they can execute you know they can get the You know, the simple things done and be able to be agile, to be able to build a team that, that can be responsive and proactive and to think about those things and say, Hey, you know, after the holidays.

People buy pants that are a little bit bigger because we all gain 10 extra pounds. Uh, maybe we should do, you know, make sure that our stores have XYZ. You know, I was thinking about this, um, my wife has different size top and bottom for her bikini and she's like, I can never find a swimsuit ever because they're different sizes.

And I was like, that is something that probably almost every single woman in America deals with, right? Is that exact same problem. And, and yet, You know, you don't see billboards about it. You don't see, Hey, mismatch tops and bottoms, like, you know, et cetera. There's just so many insights that, that people are thinking about at the very customer level that make its way all the way to the top.

And if you don't have an infrastructure, there's a great quote from Eric Reese who wrote Lean Startup and he says like an innovation score for a company is how quickly an idea can get from the very bottom all the CEO and back down into production or into delivery. Right. And it's like, I love that idea of like, if you build this.

Build a CDO function that is embracing modern commerce, then your speed score goes up, right? You can respond faster. You can get out ahead. 

[00:21:14] Jay Topper: You know, I, you said a lot there that I, that resonates with me. First of all, yes, bras and swimsuits, any woman will tell you, are the hardest, most personal thing to try on and to feel good about yourself.

And at Chicos, we focused on the comfort and joy. And I'm, I'm trained now that, you know, when my wife says, how does this look? My first question back is, well, how does it feel? You know, first let's deal with comfort first. And it's really about, that's a very personal experience when you go into, for example, a Soma store or Victoria's Secrets or any intimate apparel store that you get very personalized attention and they're very graceful about that.

And eventually you go, wow, this is an amazing bra or an amazing swimsuit or amazing pair of jeans. And you walk out. How do you bring the charm and the personalization of that to a digital ecosystem? The flip side of that is, I can go to a digital property and within seconds I can tell you how many people have come in the last half hour, what pages they went to, how many made it to the cart, what the products were in the cart, and how many people actually checked out.

And you can actually do the same thing and bring that speed mindset into a store, because now there's cameras in stores on almost every store. And when a Person goes to the gene rack. That's basically a PDP page. When they go to the dressing room, they're kind of, you know, getting ready to add it to cart.

We're in the line for the checkout. They're in the cart and you can actually start making decisions in the store real time based just like you can on a website when you're moving products along. So there's kind of a bi directional, you know, thing that happens there. And as far as speed goes. I'm a speed freak, and to the point where the people around me, direct reports, partners, you know, question that I go too fast and that I take risks.

I really don't. I don't look at myself like that. I've never not had an out. And I believe that speed is really important, especially if you could put it in little chunks, so you're not really committing the whole world, you know, to one particular initiative. But at the end of the day. If you can do it tomorrow and you know, why wait two weeks.

And I fundamentally agree with the concept that the retailers that understand speed to market is gonna be one of the things that is gonna help them win. And then how do you put the infrastructure around that? I could not agree with that statement anymore than I currently do. I, 

[00:23:30] Ian Faison: I. I love it and I love the idea of being a speed freak because I mean I think people overanalyze everything in business to be fully honest and they think that they're making the decision with like the most information possible and that they're really not anyways.

So it's like, I've, as I get older and I don't know how you feel about this, you know, you got to trust your gut and back, you know, back it up with data because there are decisions where it's like, okay, well, let's get in the market and let's test it. Let's figure it out, right? And that, and you just don't know.

And you just hear so many examples always of, hey, we tried this thing. We didn't know if it was going to work, didn't seem like the best idea, and Oh, people loved it, but actually they did this, you know, like actually they turned it inside out and that's how they wore the jacket. And you're like, Oh, crazy.

Didn't think that was going to happen. And I just, I totally agree that if you build your team with a strong foundation, that speed can happen, then it can happen. But if you don't, then there's no way, there's no way to get fast. It's like we, you know, use the, you know, the cruise ship versus the speedboat analogy, like no matter how fast you want to go on the cruise ship.

You will never get as fast or as 

[00:24:43] Jay Topper: agile, 

[00:24:43] Ian Faison: so it's like you have to figure out how to build those speedboats. 

[00:24:46] Jay Topper: Colin Powell has, I've studied him quite a bit. Me too. And one of his sayings is, I don't know the exact one, but it's close, is P equals 40 to 70. Which basically means if, if, if you have 70 percent of the information, more than 70 percent of the information you need to make a decision, you're going too slow.

If you have less than 40%, you're going too fast. So get yourself in a comfort zone of 40 to 70. And I think a lot of companies are looking at that 90, 95 range. To get to a comfort before making a big decision where it just doesn't have to be that complex, especially if you have, uh, an out and in, in today's world, there's, and I hate rollbacks more than almost as much as I love speed, isn't that from an absolute value standpoint, I don't do very many of them, but.

You have a rollback and you have a contingency if you have to have one, but, but in general, I think that, that it's better to err by commission than omission. It's better to do something because the world's not standing still. 

[00:25:47] Ian Faison: What's an example of something like that, that you'd create an out? 

[00:25:52] Jay Topper: Well, I mean, I'll give you a simple example is at all my retailers I've worked for, there's typically a blackout period from, I don't know, November 1st or October 1st through peak because nobody wants to mess with Black Friday or Cyber Monday.

And I subscribe to the notion of do a release a day right up until Black Friday, like what difference does it make? As long as you have an out on that release, Oh my gosh, that release didn't work. Roll back. Okay, we're done. Three minutes later. We're good. Because companies, a lot of companies hold off for three and four months of doing absolutely nothing.

So they leave, lose a third of the year. Then you lose the holiday mentality. People come back in January and then it takes a month to get momentum. And then you're, now you're in February where you started the engine going again. And so I think that, I think other things are in today's world of microservices and modularity and all these Companies spinning up everywhere about every possible function around commerce from AB testing to search and that you can try before you buy now.

So you can actually implement something and, you know, run 25 percent of your traffic through it and actually see how good it is and make a 90 day commitment instead of a three year or two year commitment. So I think there's going to be a lot more trying in the future, which will increase speed and mitigate risk, which is really what it's all about.

And just in general, I think, you know, getting in front of executives with ideas to your point, the, you get a great idea here, how do you get that up and back down really quickly? There's really not risk in that. It's more of a cultural shift. And the risk is that. That if you're a lone wolf trying to accomplish this, you can actually hurt a company's culture versus if you have a company that's actually embracing and supporting that type of approach.

[00:27:37] Ian Faison: Well, it's nice with the CDO function for a retailer because if you have this function, that you have a decision maker who has their thumb on the P& L and their thumb on, you know, the digital customer experience and the thumb, their thumb on, you know, a bunch of different factors within modern commerce.

That, that is a decision maker who can be, you know, deputized to say, hey, you know, We, this doesn't need to go any farther than you. You figure out how your team wants to improve these things, and if we want to improve it, you just go, right? And and lowering the bar to, to decision makers that are not quite as high up on the food chain and then you can get stuff done and then, you know, like, were there things that as a CTO that you're like, okay, or as a CDO, you're like, this has to come to me, but other stuff where it's like, hey, if you feel that way, you can just go do it.

[00:28:30] Jay Topper: Boy, I mean, I've said this for. 25 years or 20 years that if all my directs come to me with something, an idea, a recommendation, and they're 100 percent aligned, they're just coming for me to sign it. Just bring me the document to sign because if all these varying people across, you know, the, the different departments I've managed are in 100 percent agreement, they're At that point, who am I to go against the grain there?

So I really do want to and try to push these decisions as far down in the organization as I can. I think that's enabling. I'm a very bottoms up guy. But a lot of that's dictated also by the CEO. For example, I'll use an example of bad news when You know, you do a release at two o'clock in the morning and something happens in the, and you have a problem on your website, bad news travels fast.

And my CEO and our ELT, I'm the person that's going to send an email out at two o'clock in the morning. I'm going to do it myself because I, number one, I'm going to be up with. People that are working this, I don't get in their way, but, and number two is, I want the executives in the company feel like they're in safe hands, and I could easily delegate that, and I don't think much would be impacted, except if you delegate that, the people are actually doing the work that you're distracting from to try to let the people know, looking over their shoulder, what's happening, but in general, the more work That, that you can get the chain of command to do to get comfortable around decision and bring you recommended decisions that you can just buy into the better an organization is going to run, you're going to have parameters, you got budget, you got hires, you know, you gotta, you know, you got CFOs and you got all, you know, all this stuff that you got to deal with within a company, but as long as you're following those guardrails, I can't think of, if we release, we released, uh, a brand new e commerce platform last, last year.

And when we first started putting live traffic, I'm making the call on that because there's, you know, there, there was perceived risk, even though, again, there was really no risk, but there was perceived risk. So there's a few things like that, that I need to know what's going on, but it's more of a. Hey, we need to make sure Jay's in the loop, then we need to get Jay's permission.

[00:30:36] Ian Faison: All right, so you have been in the lab. I don't know, where's your studious spot of your house, or where's your, where do you come up with your crazies, any ideas? 

[00:30:46] Jay Topper: I, I sit in my office on the first floor, and I'm currently reading Ernest Hemingway's short stories. 

[00:30:53] Ian Faison: Oh, amazing. 

[00:30:55] Jay Topper: Because I'm not doing a lot of content generation.

I have a weekly blog, and I've got this podcast, And so I have to have some time where I'm detaching. Normally it's much more, I feel much more tactical as a CDO because I'm in it to win it. And it's like every decision and every, you know, and you're orchestrating a thousand people across an organization before, as opposed to here where I'm mainly an individual contributor.

But I do, I have slowed myself down quite a bit to get some thoughts going in my head and think about the industry and think about the macro economics of the country and all these things that I would read articles about, but I really wouldn't have the luxury to. To pause and read. And I work for a West Coast company, so my content time is like 7am to 10am because they're all sleeping.

And so I get to clean up all my emails and I have this like period. It's the first time I've ever worked from home, so that's a little wonky for me, but I'm glad when they come online I can actually speak to humans. But it's my office downstairs. 

[00:31:53] Ian Faison: I imagine you with a quill. Quill pen with a big feather, like an eagle feather.

They use I have 

[00:31:59] Jay Topper: a glass pen and an inkwell, and I keep a journal as well. I 

[00:32:02] Ian Faison: see, I knew it. Now you nailed 

[00:32:05] Jay Topper: me, now you nailed me there. Oh my gosh, 

[00:32:06] Ian Faison: that's so funny. I did not know that you had those things, that's really funny. No, you did not. So you came up with the top 10 things That a CDO needs to know, and we're calling it the Topper's 10, which is great.

Why did you feel like you needed to make a list of top 10, and how did this go? 

[00:32:22] Jay Topper: Well, I have a document that I've created over the years that every direct report and every manager or director I've ever had work for me has a copy of it. And it's what is a director? And, and a, And I've started it by what is a director in a publicly traded mid market company, because that's primarily where I serve, sort of the two billion south, and I wanted, and everybody, a director is a really big level to get to in an organization.

If you're a manager, you're just coming in. You're not necessarily thinking of being a CEO or CDO, you're just thinking, Hey, I want to get to a director. And then after a director, how do I get to a VP? So I created a document of what it, what does it mean to be a director? And when this podcast came up, the question was, Hey, what do you think are the traits of a CDO?

And so I had one that was targeted towards C level employees. And which really isn't CDO because a CDO is a unique. So I think most of these would apply. To pretty much anybody aspiring to be a C Level, these are the 10 things that I believe are just inherent qualities necessary to be a Chief Digital Officer in a company.

Probably 7 of them are ones that I would say, I don't care what C Level you are, you need to, you know, have these traits. So I've put a lot of time and effort into just, you know, Kind of saying, hey, if I were walking into a company as a CDO or somebody I knew was, hey, these are the things that I think if you embrace these to some extent, and I'm sure some of my peers and, and CEOs I've served would, you know, may not agree with every one of them, but they're sort of who I am as a human for sure.

[00:33:51] Ian Faison: All right. Toppers, 10. First CDO, number one. 

[00:33:56] Jay Topper: So, number one is, is to know your company. And when I say know your company is take data off the table on this question. It's, you know, before I take roles, like visit the stores, even before you take a role, and not just do it so you can bring it up in an interview, but really start to understand the associates that you can see from a customer standpoint, listen to customers, You know, this is about, you know, going on glass door.

This is about just really understanding your company. When you get into a company, yes, you need to understand your company's financials. You need to be immersive with the companies, join the Facebook groups, listen to customer service transcripts, because it's really about the heartbeat of the company that you're trying to stimulate here.

And. If you understand your company and you understand your consumer, you understand your product, you can start making the connection of why the customer is interested in your company or your product and where there might be some gaps to fill. I include the competitive landscape in this. So it's just basic, you know, MBA type stuff of really, which I don't have one, by the way, but just Basic business 101 of really understanding your company, their strategy, their vision, their mission.

Like you got to have that foundation first before you can start poking holes at the problems that you need to try to figure out. 

[00:35:18] Ian Faison: Number two. 

[00:35:19] Jay Topper: Number two is data. And you need to understand the company's data. And there's two prongs to this. And one prong is even if you're, especially if you're not technical, is understand Where your data is and loosely how it's architected.

Do you have a customer data platform? How easy is it for people to access that data? Not just for management reporting, but how easy is it for people to access that data, to infiltrate experiences, to make them more enriching for consumers or for employees, look at all the reports that are out there, like every single peer I meet with.

And, you know, I say peer. I don't just mean a VP or above, I mean a peer in a group that's a manager, always ask them, Hey, what is your go to report? What do you use every day? And what's, what problem are you trying to solve? So it's really immersing yourself in data. And if that's a weak spot for you, then double down on it because that's where it's all headed.

Number three, be curious. I, I love being, I love flexibility of mind. I love being wrong. I can be opinionated. There's no question about it. And, but at the same time, when, you know, when you're wrong, when you have a really strong hypothesis and, and you're proven wrong, it's like eye opening, you know, it's like, wow, that's cool.

I didn't know we, I didn't know that would, It would impact the experience so much. I was wrong about that. I thought that would be, you know, useless and have no impact. Whatever those things are, that if you're eternally curious when you meet people, when you're learning something, I work for a software company now.

I've never worked for a software company. And so I'm learning every single day. I product marketing, I've never associated with product marketing. I've never associated with sales or product management at a product company. I certainly have managed product management and e commerce. But you gotta be curious and you can't fear the things that you fear the most.

So for some people, AI is such a hot button. Right now I am lock. I am 100% bought into to AI being very transformative and there's a lot of noise out there, but this is like a real bandwagon. You need to understand those things. And so the only way to do that is to not bring a playbook. There's an old saying that I, an old boss told me that is whatever it took to get you to this point is not going to be enough to get you to the next one, and I fundamentally believe that, so stay curious.

[00:37:41] Ian Faison: Yeah, I, if we're using the Colin Powell reference that you said earlier of that 40, knowing 40 to 70 percent of the information to make a decision, that means you're going to be wrong. Right? Like you have, it's built in. It's like with marketing, like when people try to like say like, every dollar needs to be attributable.

And it's like, yeah, but then you have no waste, right? Waste is the thing. Waste is good because if you have waste, that means you're maximizing the potential for something. If you have no waste, then it's like, could we have got 40 percent more business? 50%? 100%? Like, we don't know what, what was happening because we didn't bother to like, have any waste.

[00:38:19] Jay Topper: I, I think you're a hundred percent right on this and marketing is a great example of that because, you know, I've worked for, you know, first order profitability companies. I've worked into, you know, multi touch attribution, last touch attribution, LTV models, like all these different models. But at the end of the day, if you're not experiencing and different channels and throwing money at different attempts to do something with content and channels, And segments of customers.

You're never going to unlock what's next with regards to getting people to go to your store. And so I agree with that. 

[00:38:49] Ian Faison: Number four. 

[00:38:50] Jay Topper: Number four. And this is also a Colin Powell one, actually. I think it's my only one in here, but it's per, you know, optimism is a force multiplier. I am a perpetually optimistic human.

In fact, when the shit hits the fan, the worst, that's when, that's when the stress air just leaves me. You know, my kids will always. You know, say, Hey, dad, you know, when you, you know, when you get in a car wreck, you're not stressed at all. But if you, I forget to take out the trash, you get pissed off. And I'm like, yeah, these macro things that come at you, you know, that are big things there.

You just need to break them down and you need to be positive because that keeps positivity around you. And it doesn't mean be fake. It means literally, I don't know that there's. A business day or a business problem that has come my way that I haven't looked at it is, Hey, this needs to be a motivational solve to this problem.

And if I act like this, my directs will act like this. And if they're, they act like this, then their staff will act like this. And it just is a better way to live life in my, in my opinion. And you can acknowledge the bad. So this isn't turning a blind eye. This is just more about how your approach to problems and challenges are.

[00:39:59] Ian Faison: Couldn't agree more. Number five. 

[00:40:01] Jay Topper: Bottoms up. I've worked for companies. I've worked for some assorted cultures. I can tell you that I've worked for companies where people at my level would say, yeah, you can't meet with any of my people without going through me. And I'm always like, really? You can meet with any of my people.

You're not, in fact, I don't want you to go through me, but, and I've worked for others that say, yeah, you can talk to anybody you want, but the bottom line is if you want to figure out what's going on in customer service, go to the call center and sit with the agents. You know, you're not going to read a report and figure that out.

Listen to 20 customer calls. Take a few, you know, and which is scary, by the way, you know, the least, you know, salary, the, you know, people are handling the, the scary calls every day of their life and the chats and everything else. And, and bottoms up, if you want to find out what their pain point is, sit behind them, where they navigate their systems.

You want to understand what an accounts payable clerk goes ERP, sit down with them and meet with their managers and just. It's to me, this is about a groundswell and I have as much fun, you know, interacting with a junior analyst, building a simple report for me as I do coordinating a five vendor, 200 person team to get this massive project done.

It's all just about. Individuals and humans and no human is bigger or less than the other. Some are have more decision making and more budget, you know, authority than others, but at the same time, if you really want to understand your company, get down into the weeds with the people that are actually doing the grind day in and day out.

[00:41:23] Ian Faison: Number six. 

[00:41:24] Jay Topper: Six is my favorite. I don't know why it's number six, but it's my favorite and it's create a hero culture. And again, I'll use a contrast to two companies. You know, I worked at one company where when we would have any type of outage on anything, in fact, third party, you know, AT& T goes down or, you know, something happens in a release in the middle of the night, you know, the CEO would be like, who are we firing and yelling, screaming.

While the problem was still happening. And then I worked for another company where the C levels would come by, you know, my office knowing I'm on a bridge, sometimes lengthy for hours, and they would ask me if they could do anything for me. And do I need coffee? Is my, how's my team doing? Am I rotating people off?

Some of these big hairy ones, especially when the supply chain was bonkers during COVID, you know, and the bottom, and it creates an, the latter creates an environment where if you find the problem, even if it's in your backyard, that you're a hero and it's not a blame game. It's not a hang your head in shame.

So when a problem pops up, the first instinct people should have is to look into the area they manage. Before they start saying that might be marketing's problem. That wasn't us. That was the merchant. So wait a minute. Data didn't do this. Infrastructure's at fault. Is really look inside yourself and just value and reward the people that are finding the problems.

And then the people that are making the solutions go up on a pedestal because they're the amazing problem solvers. Both of them deserve equal treatment. And so if you create that environment, you have fearless people around you that aren't afraid to fail. And are more than willing to admit that they made a mistake, and that vulnerability, I think, is key in an organization.

[00:43:04] Ian Faison: I love this, and there's a great Steve Blank article where he talks about, also, you know, basically Godfather of Lean Startup, where he talks about a post that I think was pulled from McKinsey or something like that, that essentially boils down to, your culture is what you celebrate. And, you know, If, if, you know, somebody takes a cross country flight and doesn't sleep and pulls an all nighter and closes a huge deal and, you know, parties all night, and you celebrate that, then like that's, you're making more of those type of people.

And I always love that. I love the idea. I like that 

[00:43:37] Jay Topper: as well. 

[00:43:40] Ian Faison: Number seven, 

[00:43:41] Jay Topper: number seven is a little wonky, but because a lot of C levels including myself like to, you know, claim a strategic side of them. And sometimes I've interviewed people for VP levels and say, I really don't want to get hands on. I want to be more strategic in my next role.

And look, I love strategy and I love buying into a company strategy and I love having a hand in what that company strategy is and I love laddering it down. Well, if that's the company strategy. What's technology strategy, what's marketing, what's supply chain, and getting it so you have a nice pyramid ecosystem of how to achieve your company, you know, strategy.

But at the end of the day, I'm an executor and I like doing all that upfront work around strategy and around problem identification to achieve the strategy, solution architecture to solve those problems. And then making the decision on the partners and platforms or whatever you might use to then implement.

But man, once that implementation starts, you gotta be hands on because you can't leave that to everyone. And it's not a question of micromanaging. It's a question of the fact you've done all this work to get to know your company. You've done all this work to be bottoms up. You can see things very holistically, and you see it through the eyes of the board of directors, and there's mountains you can move when people have problems.

I don't think anybody that's ever reported to me would say I'm a micromanager, but they would all say I was hands on and involved when it mattered. And, so that execution part, Man, you know, I'd rather execute a poor strategy than execute no strategy. And I'm sure there's debates on which way, which one is better than this.

It gets back to my belief in make mistakes by commission, not omission. But if you do enough upfront work, you can be pretty confident, but don't forget about execution because implementation execution, the actual change is where the magic happens, especially if you can pivot quickly. But yep, that's it.

Execution. 

[00:45:37] Ian Faison: So. I love this. And I actually, I've changed my tune on strategy a ton recently where I was listening to a podcast and with Jason Freid, who's a techno sort of famous technology founder. And he was talking about their company and how they do planning. And he said, we don't do any planning past six months or sorry, six weeks.

And he said, and they're like, the guy's like, why did you do that? And he's like, because Any time that we found that we planned farther out than six weeks, we, and this is like product strategy, right, for a technology company, but he's like, we either, one of two things would happen, we would be sort of trying to convince ourselves The End.

that we were smart and that we could predict the future, or we would get into the future and then be dogmatic in looking back at, well, old me was smart, even though new you is way smarter because you have all this information. And so what happens is people build like a year plan, for example, or a two year plan or whatever.

And then they Stick to the plan, but it's like new information has now come to light in the past. So I think of it more that strategy is more about setting a North Star, you know, having your mission be clear and setting your North Star and saying that, you know, hey, this is our path to get there, but you have to be able, you know, if you use, I wrote a blog post about this, Dead Reckoning, where it's like the whole point is that you have to take out your compass every hundred yards and make sure that you're on course because.

There's no way through the trees unless you do that, whereas like if you just say I'm going to set the course and I'm just going to walk for five miles, you could end up, you know, extremely far away. 

[00:47:25] Jay Topper: Yeah, I think that's spot on. I've learned this at the small software company, fabric, that I work for now is that a lot of the characteristics they have.

And in fact, when I've worked for little companies that got big, like Rosetta Stone, you know, as they grow, they say, we want to keep the charm of a startup. We want to keep the charm of when we were small, or you get big companies that have long forgotten what it's like to be small and nimble and hungry and scrappy, and they, and they try to capture that.

And that's what digital first and a CDO is all about is, and you can't fail fast. If you have a year plan, you know, so I fully embrace the six week, eight week, when you do major replatform, you get people together. All right, what do we do in the next 30 days? Let's just lock that down and put all of our effort there.

And then we'll meet again and say, what do we do in the next 30 days? That it's that that's the world we live in now. And I fully, I fully embrace it and you have to pivot. Otherwise, you can't pivot. 

[00:48:20] Ian Faison: Well, you told that story earlier, which I love, about the Black Friday piece, where it's like, there's just this culture and this taboo around, hey, we just shut everything down in prep for Black Friday.

We're not going to release anything else. And you're like, that takes out half the year, practically. So we're just not going to release anything for half the year? That seems crazy. Let's do the exact opposite of that and let's release something new every day. There is 

[00:48:43] Jay Topper: always a reason not to do things.

Always. And it's budget time. It's evaluations. It's, you know, we got our 10 Qs and 10 Ks and 8 Ks we got to get out and, you know, all the different things. But at the end of the day, you know, retail doesn't sleep and they keep, it keeps moving forward. And I think you have to keep pace with that. 

[00:49:00] Ian Faison: Number eight.

[00:49:00] Jay Topper: I think calculated risk taking is critical, especially in retail that That sometimes can be a little slow to take those risks. The greater the risks, the greater the calculations you need. I'm not reckless. I've, you know, not had, you know, may, I've been fortunate not to have major failures in my career.

I've had a couple I wish I could redo, but nothing that certainly changed the trajectory of the business. And again, I, you know, I had a partner I work with, uh, that helped me implement fabric at Chico's and the woman that heads that. Relationship from a senior standpoint, she goes, I thought I was a risk taker until I met you.

And I go, explain to me why, how you think I'm a risk taker, because I don't understand it. And he said, well, you're doing this during, I go, yeah, but we could roll back in two minutes. Well, yeah, but no, we can roll back in two minutes, like badge on table, like commit that we could roll this thing back. So why is that a risk?

And it's really defining, redefining what a risk is, you know, and figuring out what is a risk to your company really. And. $50,000 to a $2 billion retailer is not a risk to a retailer. A re a re a risk to a retailer is losing 20% of your customer file. That's a risk, but it certainly isn't, you know, some of these little micro things that happen during the course.

So I'm just a big believer in calculating that risk and getting people on board to start pushing you a little bit. In fact, I love it when I'm the voice of reason, the craziest company I ever worked for. I had a CTO reporting to me. I was the CDO and I had the CEO. We were all risk takers. There was no check and balance.

Now that can get a little bit dangerous because like one person would say, Hey, I think we should explore China. Okay. I'm going to get on an airplane tomorrow. Okay, here, go do this. You know, so you like to have a little check and balance. You want some reason around you. But at the same time, my experience is that most of the time people can take greater risks than what they think they can.

[00:50:51] Ian Faison: I love 

[00:50:52] Jay Topper: that. 

[00:50:52] Ian Faison: I, in the army, one of the great lessons I had in the army is about rubber balls and glass balls. And, and I just think that there's so many people in business that feel like they're holding a glass ball and it's not. If you drop it, it'll bounce, pick it right back up. Number nine. 

[00:51:06] Jay Topper: Number nine is, is agile agility.

And it's funny because I live my life in an agile world. And what I mean by that is if I'm going to redecorate a room, you know, it's an agile process for me. If I'm cooking, you know, I cook a lot, you know, it's an agile process. I pivot, I do little things and I change. And the bottom line is, I think the day of big, massive, non ROI waterfall projects are just going away.

And you have to increment yourself to victory, and you have to figure out a way to show some value along the way. And that can be constructed. You know, when I, a lot of the replatforms I've done, the biggest risk was always, are we sequencing this right? Are we going in the right order? Sometimes you can put a little platform in that can get you a quick ROI, and then you can say, Alright, now we'll go to this.

aspect platform, now we'll go to this one, but at the end of the day, it gets back to your same principle of, of six week planning versus, you know, year planning is the more incremental you can make things. And, and certainly, uh, uh, shameless legitimate pitch fabric embraces fully incrementality. I lived it with them for two years.

The more you can embrace that, the more easily you can pivot and make changes to what your plans are and what your sequencing is. And I've made plenty of those changes. You said it brilliantly just a minute ago, like, I know five years from now, I'm going to look back on today, Jay, and go, Uh, that guy was pretty ignorant.

You got to recognize that. And I think two months from now, I'm going to be smarter than I am now, or at least less ignorant. So I think that concept of incrementality is, is absolutely critical. And yeah, it's hard to build. Every retailer does three year plans and five year plans and man, oh man, that's some pie in the sky stuff.

I mean, I do it, I play. So I don't want anybody to get stressed out about that when you have to, but I'm big into incrementality. 

[00:52:58] Ian Faison: I love that, and I love this, this is such a great lesson, the idea of incrementality. Because, you know, you talk about in like, in investing that, you know, it compounds, that in content, you know, things compound, like you get another listener, then you get 10, you know, you, all of these, you know, customers compound.

So if you're getting, you know, 1 percent better every day, That compounds, right? And, and that's not 10x, 100x return tomorrow, but over time it becomes a massive, uh, 

[00:53:28] Jay Topper: 100%. That's exactly right. 

[00:53:29] Ian Faison: Number 10. 

[00:53:30] Jay Topper: Number 10. Be genuine. And, I think I've always been genuine, I don't know. I like to think I have been. And, uh, You know, the, I'm a big fan of, uh, uh, Brene Brown.

I've watched almost all her stuff. I'm, I'm better at watching than reading sometimes. But, and it's, a lot of it's about vulnerability. Uh, at least some of her early stuff about being vulnerable, uh, what you're not good at, what your fears might be. And there's this, there's always this debate going on at offices.

Hey, you know, company's not your family, you know, and your family's your family. And look, I got four kids and six grandkids, and I know what family is. But at the end of the day, the people you're working with, they're also humans and you need to care about them. You need to hold them accountable. And you need to show them that you're a human being.

And so I prize vulnerability. I prize self reflection. I surprise self awareness. It's sort of a humility that comes with wisdom. I think if you can combine those two really well, so you can be confident and humble at the same time. And I think if you can master that, and we never do completely master it, then you can start having more fun with it, especially if it's attached to performance, because I don't ever want to let accountability slip, but that's not the same thing.

So I think just be yourself as much as you can, as much as you're willing to open up who you are as a person to the people around you at work. And I think that ends up being. You know, something that's very powerful and people come to respect and admire it. And I certainly do. And the leaders and the peers that have shown that to me, and I've come up through a world where I've learned that, that, that I don't turn on and off myself just because I walked through the doors of a company.

I try to stay true. I try to stay true to I am including the mistakes I made and the successes I have. I try to stay true to myself as best I can when I walk through the doors of a company. 

[00:55:21] Ian Faison: Jay, it's been wonderful chatting with you today. I'm so excited to listen to this show. We have some amazing guests coming up.

We have some amazing conversations. I can't wait to hear you talk with all these CDOs. Wonderful chatting with you. For our listeners, you can listen to new episodes of Chiefly Digital that are going to be coming out and, and you can connect with Jay on LinkedIn. Jay, any final thoughts? 

[00:55:44] Jay Topper: No, Ian, you were awesome.

I really appreciate the experience and I appreciate the time that I Got to spend on just building some content I believe in. So this was a lot of fun for me and hopefully it brings some interest to a few people after we get it out there. 

[00:55:56] Ian Faison: Indeed. All right. Take care. 

[00:55:58] Jay Topper: All right. See ya.