Retail Podcast 710 Naomi Wheeless: Devising a Seamless Retail Strategy

Bob: Today I’m talking with Naomi Wheeless, Global Head of Customer Success for Square. Welcome, Naomi.

Naomi: Thank you. Happy to be here.

Bob: Glad to have you. Now most of us know Square is that little small thing that we stripe our cards with, but can you give me some context or stage what Square does for those who don’t know that it does a lot more than that?

Naomi: Yes, absolutely. That’s definitely the thing that we’re probably most known for. But we actually started about 13 years ago, and our mission is economic empowerment. What that means is that we’re really passionate about ensuring that anybody who wants to start, run, or grow a business can do so using our huge ecosystem of tools. So think about software and hardware that’s necessary to run your business.

So, we’re offering solutions for everything from, obviously, taking the payments, but financial services, Buy Now, Pay Later, how to manage your staff and pay them through payroll, and financial services. And we do this for a number of different verticals within the entrepreneurship umbrella, like retailers, restaurateurs, business and personal care, and a lot of other people as well. So, that’s really what Square’s all about, is making sure that if you want to start a business, that you have everything you need to be successful.

Bob: Well, excellent. And what do you do at Square?

Naomi: Yes, so my official title, which is kind of boring, is the Global Head of Customer Success. And really what that means is I have the privilege of running a really large team that’s all about making sure that Square shows up well and feels good to the customers. So, my team is the team that interacts with customers over the phone, email, social media, on our huge seller community. We really make sure that if you want to speak with Square, we’re the team that you’re going to be talking to. And so, we’re in charge of the experience that you receive.

Bob: Wow. That’s quite a job description. My goodness. Well, let’s go back a little bit. You and I share the Buckeye State. But I think your first job was in a call center, is that correct?

Naomi: It was. So, while I was attending undergrad at Ohio State University, I noticed that a lot of my friends were getting jobs at this call center that was just down the street. And so, I went over there and got a job as well. And I started on the phones making $12 an hour and was taking insurance calls, and did that and just really worked my way up. I started there when I was a sophomore. And by the time I graduated, I was running the whole site.

And I really fell in love with running huge operations, particularly in the contact center environment because it allows me to be able to do two things that I’m really good at and passionate about. One is I have a seat at the table to be able to influence the strategy of the organization because I am the person bringing the customers’ thoughts and their insights, but I also get to influence a huge portion of the employee population base. And I like developing people and watching people’s career grows.

Bob: Now, I started back in the 80s. And I was very young, and I was managing older people. So I had to grow a mustache because back then, you just didn’t trust a kid to manage other people. And you must have run into something like managing managers who are older than you. That’s got to have special challenges, doesn’t it?

Naomi: Yes, absolutely. I tried very hard to hide my age. Everybody knew I was young, but I tried to make sure they didn’t quite know how young. And so by the time I was a senior, I’m, what, 21, I guess, years old at that point, and I have three layers of management under me at that point because I’m the director and some of these people are 55, 58 years old.

And so I did run into what I call reverse ageism where some people struggle to report to somebody so young, so I had to work very hard to prove myself. But I definitely gained the respect of the entire leadership team relatively quickly. But yes, it is definitely a challenge when you’re as young as I am and you’re managing people who are, in some cases, as old as your grandparents.

Bob: Yes. All right, so I have to stop there. So, what’s one tip? I mean, that’s a great point that you had to prove yourself, right?

Naomi: Yes.

Bob: That probably is number one, that they’re waiting for you to fail. You’re inexperienced, you’re stupid in the ways that they are. They know so much more, but yet they’re also kind of jealous because you got the job. So, any tips there?

Naomi: I think it’s service leadership, is a huge piece of it. So, walking people through things, making sure that you’re in the trenches with them. And quite frankly, to some degree, you have to kind of show them that you know what you’re doing. So I use the leading-by-example philosophy a lot. So I would make sure that I have the doubters, is what I would call them, in my presence when I’m doing things that I know they think I can’t do to essentially prove to them that I can do this, not just do it well, but I’m actually doing it better than you do. And so, by doing that in a very nice way, a subtle way, it allows me to tell them that I deserve this role without having to say that.

And subconsciously they start to start respecting you and admire you. And I’ve had so many people just sit me down and say, “How did you get to be this way at 21?” Mind you, this was years ago. I’m not 21 anymore. And it was just really, really a great experience. And I think it helped me prepare for the rest of the career that I was going to be climbing for the next couple of years because when you have to work that hard to prove yourself, you just naturally develop a more resilient work ethic than you probably would’ve otherwise.

Bob: I love that. And I love the idea of challenging yourself to be doing it in front of the doubters. That’s a great point that I think most people miss, that it’s easy to have your people believe in you. That’s not the problem. The problem is you got to get everybody on your staff. So now talking about building teams, you wrote an article for Forbes about how you focus on building diverse teams. And everybody talks about diversity, I think, nowadays, but let’s face it, what does success look like?

That’s the challenge I think every organization, no matter whether you’re a small retailer, you’re a restaurant. Is it something that is dynamic that everybody should just, “Here’s the sentence to memorize,” or is it something that we have to come to? I believe diversity is what makes everybody great. I mean, we’re more alike than different. That’s my philosophy, and I’m sure it’s yours as well, but different voices at the table make us all stronger. But how can we do that?

Naomi: Yes. I think that is very important. You can’t have a really successful business if it’s not diverse. And diversity is more than just race. Of course, it’s race, but it’s gender, it’s age. It’s just set of experiences that your employees are bringing to the table. But the most important thing is if you’re going to make a commitment to have a diverse workforce, that it really has to start at the top. So, oftentimes what happens is a company will say, “Oh, we’re going to become more diverse,” and HR says that we’re going to do this, and they roll out some type of goal, but you never hear the most influential people at the organization speak about this as well.

So it really has to start with the CEO. And if you’re running your own business, that’s essentially you. And so whatever you deem as important, whatever you say, “This is what we’re going to work towards,” is what the company will obviously focus on. And like we all know, if it’s not measured, it doesn’t really count. And so having goals and publicizing those goals and being transparent with how you’re doing is just really key to the overall success.

Bob: Okay. So, starting at the top and making sure that you’re messaging it at the top. Now, you said in an interview, and I quote, “I was confident enough in myself to not be afraid to leave a company after several years to gain a new experience elsewhere.” so many people get caught in indecision. So how do you develop that confidence? Because clearly, you’ve landed on your feet everywhere you’ve gone, and look at you today, but that confidence is what had to drive you when you came to a decision.

Naomi: Yes, absolutely. Confidence is probably the number one characteristic that’s helped me achieve what I have at a relatively young age. Some people are lucky enough like me to just be born with it, or they’re born into an environment where that’s just naturally cultivated. I come from a very heavy military family. Both my mom and my dad were in the army for over 20 years each, active duty. Both grandparents, all aunts and uncles, everybody was in the military.

I was in the military for a brief time as well. And I think just growing up in that environment, it helped me from the time I had diapers on just really become a super confident person that believes in myself. And I just have this, I guess, air about me that I believe I could do anything. And if I don’t know how to do it, I just feel like I could figure it out. But there’s other people who weren’t maybe as lucky to grow up in an environment where that’s naturally instilled in them from an early age, and they have to develop that over time. And it’s something that you have to set goals and you have to have checkpoints with yourself.

And sometimes as much as it’s distasteful to say, you have to fake it till you make it, you have to put yourself in these really uncomfortable situations you maybe normally would try to avoid, force yourself to stumble through them, seek the uncomfortable feedback, keep practicing and iterating until it becomes more second nature to you to just have the confidence to do whatever that thing is, whether it’s public speaking or to put a divergent perspective into a conversation when everybody else is saying another thing.

So, confidence means a lot of different things to people, but you really just have to figure out what is it about you that is making you lack confidence. Is it you are worried about being laughed at? Are you worried that you don’t know you’re going to sound stupid? Figure out what is the culprit of your lack of confidence and then figure out what’s the best strategy to attack that.

Bob: Yes, I agree with all of that. And the mindset, the chatter in our heads, “You can’t. There is no way you can.” You have to say, “Who’s saying this?” I mean, we wouldn’t let our best friends say stuff that we say to ourselves in those moments. And to your point, before I go onto a stage, yes, there’s always a moment where it’s like, “We’re all human. Will they like me?” And you have to be willing to move past it.

I also like your idea of seeking out the uncomfortable feedback because then you’re not afraid of it. Because a lot of times, we put things into people’s minds like, “Oh, she hates me,” and then you talk to her and it’s like, “Oh, yes, I was upset that my coffee was cold. It was not about you.” And you’re like, “Wait, what? I thought...” Because we bring our own demons to the table. And so that confidence comes in steps, and I think, to your point, making a decision to just say, “I’m going to be confident,” and then see what happens.

Naomi: Exactly. And the feedback is important because, obviously, that’s how you get better, but then also it helps you to realize that a lot of times, you weren’t as bad as you thought you were. And so you’ll start to realize, “I don’t actually suck. I didn’t bomb that presentation,” or, “That interview wasn’t as bad as I thought it was.” And you’ll realize that that self-doubt, whether it’s imposter syndrome or otherwise, is really eating away at the confidence unnecessarily.

Bob: Yes, no. Excellent. Good stuff. Well, I should probably get back to Square because that’s what we’re talking about here. What does Square’s technology play help in building a great customer experience? I know you’ve got a lot of tools that can help, but just a few of them that might be something most of our listeners never heard about or really used.

Naomi: Yes. Like you said, we’re mostly known for the little white card reader, but there’s a whole entire ecosystem of solutions. And so, I’ll just call out a few of them. One that really is useful for retailers is inventory management. So, whether it’s the holidays or not, you want to make sure that your inventory management is in lockstep across all of your locations if you have multiple locations because nothing causes more customer frustration than you telling them that something’s in stock, whether online or in person, and it’s really not.

And you don’t want to be caught on the back foot of thinking that you have something to sell and you really don’t. So, Square has inventory management software that will really make all of your business decisions easier. You’ll be able to analyze your sales reports from last year to help you forecast what will likely happen this year by identifying those trends in the data.

And that just allows you to plan better for items that are going to sell quickly. You’ll understand which ones are likely to run out sooner than others, which ones maybe you want to pull off the shelves because they’re not going to sell as much as you think they will, and when maybe you should offer sales or discounts or other type of promotions on certain products that you have.

Our inventory management software also allows you to have easily-downloadable reports where you can update your inventory quantity in bulk versus one by one. It’ll also give you probably the coolest feature is a daily stock email alert so that you know real-time when something’s running low and you can get ahead of it and so that you don’t miss out.

Another thing that’s really cool about our ecosystem of solutions is our customer relationship management software, so CRM. Whether it’s loyalty, marketing, that is just so imperative to do this really well so that your customer experience is just flawless and all tied together. The goal obviously is that you want to be creating repeat buyers, people who are coming back to you time and time again, and having good CRM software will help you do that.

So, you do that through things like having marketing campaigns that speak to personally that particular seller and things that they’re interested in, and loyalty programs that reward them for coming back over and over. Those are just some of the things that exist within the ecosystem of solutions that will really help you build a more unique and differentiated customer experience.

Bob: Nice. I was just reading today how Starbucks adds a million dollars, billion dollars a year to sales, is they say the key is their customization through the app. They said nobody has the ability to make it just for you. And I think that’s where we’re all going. That data that Square has got and now Afterpay, we’ll talk about that in a sec, can give a retailer, can help you be really personal instead of, “Let’s just throw an ad out there.” You can be really focused and probably get a higher return. That’s kind of the whole thing.

Naomi: Absolutely. You’re able to tailor things down to certain cohorts of sellers. Sellers that like this, you advertise this to them. So, you’re matching their preferences so that they feel like you’re getting a more personalized experience because isn’t that what we all want? We all want to feel special like we’re the only customer.

And so, when you’re tailoring that marketing, you’re giving them a rewards program that feels like it’s actually bringing additional value, they’re just so much more likely to come back. And especially if you couple all of that with omnichannel solutions where you’re meeting them wherever they are, whether they want to purchase on social media or your website or in person, you’re just set up so much more for success that way.

Bob: Nice. Now, we always talk about generations in retail now and like, “Oh, if you’re not on TikTok, you’re being left behind.” Well, for some brands, that’s definitely true. But one of our first guests was the Founder of Afterpay, many years ago in Australia. It’s been great to see how you two have come together. In fact, on my Facebook Live video just a few days ago, a woman said, “My Square has now said, ‘Do you want us to add Afterpay?’ And I don’t know if I should do that.” I was like, “Of course, you want to do that because young people are expecting that.” So, what generational differences do you see through all of the information that Square is gathering?

Naomi: Yes, absolutely. So, there’s a lot of commonalities across the generations. Like, for instance, everyone wants to feel special, everyone wants to feel like they’re getting a personalized experience. But there’s definitely things that are unique to the various generations. So, for example, younger customers, they really want experiences. They want to feel like a sense of community and belonging and a deeper connectivity to where they’re spending their money, essentially.

They also are really attracted to Buy Now, Pay Later options for obvious reasons. Younger people are starting out in their career. They tend to have less money than the older customers who’ve been working for many, many years. And so, anything that they can do to stretch their dollar to allow them to still maintain a good lifestyle, they’re very attracted to. And so, you want to make sure that you’re thinking about offering that type of service, both online and in person.

And then we have the Gen Z generation. They’re really attracted to like huge big promotions that are not reoccurring, so like Black Friday and Cyber Monday. These are things that really attract those folks while you’re older shoppers, as it relates to the holidays, they tend to wait more till December to actually go buy their stuff. And then older shoppers also, they’re really into gift giving.

They want purchases that are meaningful, that connect to people. They want to create something that builds a relationship and is admired by others as well. So, we want to think about what are the blanket things that everybody wants to feel, but then making sure that you’re tailoring to whatever your customer base is or what you want it to be as it relates to various age groups.

Bob: You’ve now identified me as an older customer. Thank you very much.

Naomi: You’re welcome. Nothing wrong with that. We’re all going to get there one day.

Bob: That’s right. So, I’m intrigued. How can you give great customer service when you can’t see the person? Because that’s the world I work on is face-to-face, that’s what people come to me for. And a lot of times people say, “We just don’t do well when we’re on the phone.” How does that happen? Because we talked about confidence earlier, and I’m sure training is a priority for you, of course, but how can you give great customer service when you can’t see the person?

Naomi: Yes, absolutely. So, you want to make sure that everything that they’re touching, everything they see, touch, and feel as it relates to your business is just world-class. So, a great website is a huge piece. You want to have a social media presence that is clear where they can see and understand what you’re selling, what the value proposition is of your various products or services. You want to make sure that when they have a question, that you can meet them wherever they are. You never want a customer to feel like they want to reach out to you and they can’t do so by the method that they prefer.

So, make sure you have great response times on your email and that your email address is published somewhere where they can see on everything. You want to make sure that when they call, that the calls are getting answered quickly by a friendly person, but, most importantly, by a knowledgeable person that’s empowered to take care of whatever the task is to answer the questions and that they will hang up feeling like, “Yes this is the right place for me to spend my money.”

You want to make sure, I think I mentioned social media already, but it’s such a huge place where people are now conducting business. And so, making sure that you have ports for them to actually make the purchase on social media where they don’t have to leave the app. Connecting everything is just so, so important. And so, you do all of these things, you will make sure that you’re driving the customers into your business and allowing yourself to have multiple avenues of revenue streams, that you’re not required to just have them physically coming in because a lot of people just are moving away from that for one reason or another.

Convenience, the gas prices are too high to drive to you or whatever. People just don’t want to come in all the time the way we did maybe five years ago. So, when you nail the customer experience all the other ways that your business touches their lives, you drive revenue, you create those repeat buyers, you strengthen your brand marketing and your brand loyalty, and your NPS, so the rate at which your customers will refer other people to you, all of these things just exponentially get better.

Bob: Excellent. So we’re going to take a little break, but I want you to be thinking about what are some pitfalls to promoting someone too early. A lot of us are understaffed and we’re thinking, “Oh, what are we going to do?” And they’re just promoting people up. When we come back from the break, I want you to be thinking what’s some pitfalls to promoting too early.

Naomi: Sounds good.

Bob: So, what are some pitfalls to promoting somebody too early, and how do you deal with that?

Naomi: Absolutely. This is one of the things I’ve seen time and time again throughout my career, unfortunately. One of the main reasons why people end up getting promoted too early is because they are an amazing producer or amazing at the original job. And we’ll just use sales as an example. What often happens is your top sales producer gets promoted to sales manager. It could be a good thing, it could be the right decision, but it’s not always necessary that it is.

Just because somebody is great at Job A does not mean they’ll be great at Job B. So, you can be amazing at selling. You know how to overcome objections. You’re great at being charismatic with the customers and you’re converting a lot. But when you become sales manager, you now have to figure out how to replicate those skills across a team of 20 salespeople. You have to have great leadership skills. You have to make your team feel inspired and motivated.

They have to want to work for you. And just because you were good at the job does not mean you have leadership skills automatically. It does not mean you have strategic planning skills and great decision quality and you’re a great communicator. So, it’s important that you’re thinking about the full suite of needs for the role that you’re going to be hiring somebody into and really looking at, does the person that you’re considering promoting, do they already have all of these things, or are they malleable enough to where you can develop them to develop all of those skills that are necessary?

And oftentimes the answer might be no. And so, you also have to make sure that you’re thinking about promotions in the right way. Oftentimes people or business owners or corporate leaders, they’ll throw out a promotion as a carrot to keep a person or as a reward of, “Hey, you’ve been doing a great job, here’s a promotion.” And I think from my personal perspective, that is very much so the wrong thing to do because a promotion isn’t a reward for good behavior or good productivity.

It’s not a reward for being loyal to the company and staying around for a lot of years. A promotion says there’s a business need for a new role and we’re clear and we’ve identified what those needs are and you meet those, or we believe that you can meet those. So those two things have to be true in order for the promotion to really make sense. When somebody is just doing a great job or you want to incentivize them to stay, there’s other ways that you can reward them other than a promotion that won’t cause detrimental harm to your business.

You can give them a raise. You can give them additional responsibilities that doesn’t necessarily necessitate a promotion. You can give them a physical award. You can do a lot of things and still make them feel good, showing them a lot of kudos and appreciation without harming your business. And remembering most of the time when somebody gets promoted, especially if it’s into leadership, that person’s not going to be affecting the enjoyment, if you will, of a lot of other of your employees. And you want to make sure that you don’t make things great for one person and bad for everybody else because you put the wrong person in that role.

Bob: That could be the best couple of minutes on this podcast. That is a lesson in promotion, which I think few people understand. And I loved your idea that there’s first a business need, that it’s not, “Oh, we need to find a way to give her more money.” And that leads me to my next question, which is, how do retailers find time to prioritize training staff? Because training has got to be important. You’ve got a couple of thousand people around the world that are responsible to you. I’m sure you just don’t say, “Yes, go whatever you want. Just go do what you want.” So how do we find time for that? Because that’s probably the number one thing I hear people say, “Oh, we just don’t have time to do it.”

Naomi: You have to figure it out. There’s nothing more detrimental to your business than putting an employee in your operation, whether it’s customer-facing role or not, that isn’t prepared. If you don’t nail their onboarding experience and their subsequent training, they are generally unhappy. So, they’re going to end up quitting or getting fired because they’re not doing a good job, which means you now have extended overhead costs because you’re going to replace them. Where if you just did a good job to begin with, they would’ve stuck and you wouldn’t be wasting this money.

So, I don’t care what you have to do, you have to figure out how to nail onboarding and training, whether you just build it into your overall operations model or you do it after hours, and for maybe their first month, they just get overtime. It’s so important that even if you had to adjust your hours of operations temporarily to get somebody up to speed and take that revenue loss for a little while, if you get it right, it will, for years to come, make things so much better.

Because nailing the onboarding and training means that that employee is happy and healthy, they’re doing great work, they’re providing a much better experience to your customers, which means more repeat buyers, and they’re likely to stick around for a long time, which means you don’t have to go through that pain of hiring and doing all those interviews and training somebody over and over and over again.

And if they stick around for a long time, they’ll be able to take on additional responsibility, which means you can elevate to look up more and focus on things like the strategy and other things, and that be so bogged down with the minutia. And maybe they eventually will earn a promotion and do bigger things for your business long term. So, it’s a short-term sacrifice. Did you figure out how to make the time and the space for that? How do you create that psychological safety where that employee feels like they can be vulnerable to ask questions? If you nail that and get it right, it’s a short-term pain, a short-term cost that will just reap enormous long-term benefits.

Bob: I love that. You got to nail onboarding, folks. That’s the key. Onboarding and then training. I loved your idea. Otherwise, they don’t feel safe enough to be vulnerable. A little Brene Brown there in our morning here together about that whole being free enough to expose yourself. And if they aren’t free enough to do it, they’re going to leave pretty quickly because, let’s face it, I think there’s two jobs for every one person right now.

Naomi: Yes. We don’t have a luxury anymore of, “Will they need this job?” Most of the time you need them more than they need you at this point. And if you are going to lose somebody, making sure that you’re doing exit interviews, that you’re collecting the data about why they left, maybe what you could have done better so that you can get it right the next time. It’s a really important step to not forget.

Bob: Excellent. Thanks for that. Now, I know Square had a holiday report and it was filled with information about inflation and people looking for deals and stuff. How can retailers combat inflation, do you think?

Naomi: Oh, my gosh. Inflation is the bane of everyone’s existence right now. And so entrepreneurs and retailers are definitely thinking about this as we are here at Square. So there’s a couple of things that they can do. Retailers should start by analyzing their profit margins and figuring out what are all the things that are making me money, what are all the things that are costing me, and helping to cut your expenses as soon as you possibly can in ways that will create sometimes some pain, but not as much pain as if you’re not on top of this stuff.

And so, the way Square can help you by analyzing your profit margins is, again, keeping track of your inventory and understanding where you are with that, but also helping you keeping track of your staff and understanding what are your busy periods, what are your more quiet periods or maybe you don’t need as many people or you can reduce their hours or something of that nature.

So if you staff your store in the most smart way possible, especially in these busy holiday seasons, whether it’s things like just hiring seasonal workers instead of permanent workers, all of those things will help you really make the most of your profit margins and that will help you when you’re trying to combat your inflation. The next thing is, again, going back to nailing those repeat buyers by having a really good CRM software.

If you have those loyal customer bases, then you have to expend less effort to keep getting net new customers. And so, building a loyalty program that will naturally drive that repeat customer base, adopting marketing software to automate the campaigns for you, whether you want to recognize customers on their birthdays or on their anniversaries, or remind them the last time they bought something and maybe it’s time to re-up or something like that nature, the more you can bring automation into this process as well.

It allows it to still feel really personalized to the customer, but it takes that workload off of you. And so doing a lot of those things will help you adjust your profit margins, really combat inflation to the best of your ability, and thereby letting you survive and possibly even thrive in these unique economic times.

Bob: Yes, I agree. I think of a florist I’ve used to deliver flowers all over the nation. And the best ones, I’ll get something a week or two before that says, “Hey, Mary Jane, it’s her birthday,” or, “Last year you sent this arrangement, do you think you want to send it again, or do you want...?” I’m like, “Holy gosh, this is great.” Because I think so many people forget if we just remind them we’re here, they’ll be loyal to us. When I was working with Yamaha, and they said, “We’re kind of the underdogs. We’re not the brand that people have tattoos on their butts for. We have to work harder.”

And I said, “Yes, that’s true. Harley Davidson, everybody knows it. But every brand is like that. You’ve got to remind them that you’re still around. You’ve got to remind them that, “You liked us once, you’ll probably like us again.” And being able to have that data makes life easier, especially when we get into January and February when, let’s face it, footfall always falls off regardless of whether demand drops.

Naomi: The reminder that you’re speaking of, especially in that flower example, is super important. But the second part of that equation is making it really easy for them to do the thing again. So, you can’t just say, “Remember to purchase this,” but then create a lot of work for the customer to remake the purchase.

You want to have a single button that says, “Re-Order,” that takes them right to wherever they need to go and really simplifies and streamlines the process. Because if you remind them and you make it super easy, that drives the business because the reminder without the ease still puts the work on the customer to have to do something, which means they’ll forget to do it later.

Bob: Great. Great point. Thank you so much for that, Naomi. I know some of these people tell me how great their website is and it’s like, “Why don’t we just do a joint call?” I’ll go through with it, and I’ll sit there and like, “What do you want me to do here? “Oh, we want you to read.” It’s like, “What do you want me to read? All I see is you’re open during Covid. That was a year or two ago.” And they haven’t looked at it like a customer does, right?

Because you and I are talking about, it’s friction if you make me think it’s friction because my phone’s going to ding or clock or do something, and I’m going to go away from your website, or I’m going to go look at an app. You got to make it easy. And the more frictionless, the more you can just make it, “Yes, here is the Buy Now red button.” You don’t have to be cagey.

No, Buy Now. Make it easy. This is what we want you to do. So, we’re towards the end of our time here, and it’s been great, great nuggets here about merchandising and marketing and customer service. I love all of that. What innovative technology do you think retailers should be paying attention to and adopting?

Naomi: Probably the coolest thing that I’m most excited about is conversational commerce. So historically, we’ve communicated with companies we want to purchase things from over the phone or through email. That’s basically it. But there’s so much new technology out there now that allows two-way communication between the seller and the buyer via SMS and sometimes email, but SMS is the most exciting part.

So if you have an app, make sure that you bring in technology where customers can contact you through the app. If you don’t have a great app, there’s all kinds of solutions definitely that Square has that allow you to communicate just over text message. People love that. They want to be able to be in a meeting at work or whatever and still communicate and place an order or ask questions without having to pick up the phone and call.

And they like the fact that that’s asynchronous so that they can send a message, you reply whenever you reply, they reply whenever they reply, and it feels like they’re chatting with a friend. And it doesn’t have to be something that they have to block off time to get their questions answered for. Conversational commerce just helps sellers become more seamless and lets their customers reach them in the most intuitive way possible.

You can also do other really cool things like send checkout links directly through the SMS. So, imagine you’re going back and forth over checks with the customer and they’re like, “Yes, this sounds great. I think I want that.” And boom, you can just email them a link to what they can just click one button and enter their credit card information. You can send invoices through SMS now and even personalized coupons that really help that customer, again, feels super, super special.

And don’t forget gift cards as well, especially in the holiday season. So conversational commerce is just something that you can do as a retailer that will help set your business apart because a lot of your competitors probably won’t be offering that.

Bob: Yes. I know when I see if I miss a call and that little red dot shows up next to my phone, I’m like, “Oh, crap, I’ve got to call someone back, really.” Whereas if they just left me a text, I’d be great, so like, “Oh, what do you need? Oh, ding, ding, ding.” And we forget again, listeners, what does it feel like to be a customer on your site?

What does it feel like to be someone who doesn’t know the ins and outs of your system? Do they feel vulnerable enough to give you their email or their text number? And that’s gold because if they’re doing that, buyer intent is really high. They’re not looking if they’re... If they’re texting you, they’re not just thinking about it. They’re pretty serious.

Naomi: Yes.

Bob: So, Naomi, we’re at the end of our wonderful time together. Thanks so much for joining us. And the name of the title of the podcast is “Tell Me Something Good about Retail,” so tell me something good about retail to close us out, please.

Naomi: Yes. Retail’s probably my favorite vertical, and the reason is just looking at how resilient retailers have had to be in the last couple of years is just mind-blowingly astonishing. Retailers have had to adapt and pivot. They’ve had so much thrown at them and they’re still here, whether it’s fighting through Covid, the height of that couple of years ago, as we were just speaking about earlier, inflation pressure that they themselves are feeling, but also that their customers are feeling so they’re navigating it from both fronts, supply chain issues, labor shortages.

There’s just so many things that have been hurdle after hurdle that retailers have had to navigate through. And they’ve done so in the most elegant and humane way and are still here fighting through the battle. And many of them have come out stronger on the other end. And so their willingness to try new technologies, new offerings, figure out better ways to connect with their customers, all of these things together just make that entrepreneurial journey just so amazing for me. So, I’m super passionate about retailers, and I just think that their ability to navigate through all of that in a relatively short amount of time just makes them just most amazing population ever.

Bob: I couldn’t say it better. Thanks so much for joining us today, Naomi.

Naomi: Absolutely. I appreciate you having me.

Key Links


Naomi Wheeless LinkedIn

Square.com