Talk Commerce - Casey Drake Endear SalesChat

Revolutionizing Retail: Endear’s Casey Drake on the Power of SalesChat and Clienteling

In this special partner episode of Talk Commerce, we’re thrilled to have Casey Drake, the VP of Sales at Endear, join us for an insightful discussion on the future of retail CRM and clienteling. Sponsored by Content Basis and Endear, this episode contains valuable tips and strategies to help you supercharge your online sales and build stronger customer relationships.

The Game-Changing Power of SalesChat

One of the key topics Casey dives into is Endear’s revolutionary SalesChat feature, which transforms how brands connect with customers online. As Casey explains:

“SalesChat is a live chat widget on your website. It’s Endear’s what we’re calling our live chat feature is SalesChat. And we put that word sales on it for a reason because it’s meant to be and separate itself from a traditional support chat widget that people might be used to putting on their website.”

By empowering store associates to engage with customers through SalesChat, brands can create personalized shopping experiences that drive conversions and foster long-term loyalty.

Bridging the Gap Between In-Store and Online Sales

Another crucial point Casey raises is the importance of breaking down the walls between retail teams and e-commerce teams. Too often, these teams view each other as competitors rather than allies. However, as Casey points out:

“I think the only way you get that wall broken down is with like, we need to have a conversation about attribution and how store associates can get attribution for online sales. It doesn’t need to be every online sale, but give them a way to do that.”

By providing store associates with the tools and incentives to contribute to online sales, brands can create a more cohesive and effective retail strategy.

Talk Commerce - Casey Drake
Talk Commerce – Casey Drake

The Importance of Hiring and Empowering the Right People

Throughout the episode, Casey emphasizes people’s critical role in the success of any retail strategy. As he wisely states:

“I think so many brands need to like really take their hiring process seriously and then treat the good ones that they do get, treat them well and put them in the positions to succeed. Cause that like none of this works if you don’t have good people.”

Brands that want to deliver exceptional in-store and online customer experiences must invest in talented, trustworthy store associates.

Embracing the Future of Retail

As the retail landscape continues to evolve, brands must adapt and innovate to stay ahead of the curve. By leveraging cutting-edge tools like Endear’s SalesChat and prioritizing clienteling, brands can unlock new opportunities for growth and success.

So, if you’re ready to take your retail strategy to the next level, be sure to tune in to this value-packed episode of Talk Commerce featuring Casey Drake. Trust me, you won’t want to miss the incredible insights and actionable tips shared throughout this conversation.

Jason Sidana

A Deep Dive into Growth, Partnerships, and Staying Connected with Customers: A Conversation with Jason Sidana and Madeleine Anderson

Hello everyone, I’m excited to share with you a fascinating conversation I had with two exceptional guests, Jason Sidana, Chief Growth Officer at Maxburst, and Madeleine Anderson, Partner Manager at Endear.

Jason Sidana | maxburst
Jason Sidana

Meet the Guests

Jason Sidana is a man of many hats at Maxburst, a web design and development agency. He juggles sales, marketing, and project management while focusing on the company’s growth and helping clients achieve their growth goals. Jason’s passion for business is evident, and he enjoys delving into operational and management books.

On the other side, we have Madeleine Anderson, who is based in Fargo, North Dakota. As the Partner Manager at Endear, a CRM and clienteling tool for retail brands, she handles co-marketing activities, lead generation, and events with partners. Madeleine is also passionate about triathlons, which adds an interesting twist to her personality.

Jason’s Journey into the Industry

Jason’s journey into the industry is rooted in his family’s footwear and apparel stores. This exposure sparked his interest in retail, leading him to build a custom POS system and expand into wholesale and various sales channels. This entrepreneurial journey eventually led him to start his own agency, which later merged with Maxburst.

Maxburst’s Holistic Approach to Client Growth

At Maxburst, Jason and his team take a holistic approach when working with clients. They delve into the granular details of the business’s operations, including logistics and staff management. This comprehensive understanding of the client’s business allows them to identify areas for improvement.

The Power of Partnerships

Jason emphasizes the importance of partnerships when building a tech stack for clients. He believes that it’s impossible to do everything on your own and that finding good partners in the ecosystem is crucial. By collaborating with experts in specific areas, such as CRM or middleware integration, they can provide comprehensive solutions to their clients.

Leveraging Sales Staff as a Marketing Tool

Jason shares an interesting insight about using sales staff as a marketing tool. He realized that there was downtime during lunch hours and late evenings when the sales staff could engage with customers and potentially increase sales. This benefited the sales staff by earning them extra commission, creating a seamless customer experience, and improving overall satisfaction.

The Importance of Merging Retail and E-commerce

Madeleine adds to the discussion by highlighting the importance of merging retail and e-commerce. She explains that in the past, retail was seen as a stepping stone towards e-commerce, but post-COVID, retail has become crucial for quick and convenient product access. The omnichannel concept has gained significance, emphasizing the need for businesses to have a cohesive presence across multiple sales channels, including retail, online, and marketplaces.

Staying Connected to the Customer

Jason discusses the concept of companies losing their soul as they grow larger. He shares his personal experience of staying connected to the end consumer by working as a salesman in his family business. By doing so, he gained valuable insights into customer trends, preferences, and needs, which helped him make better decisions regarding purchasing and customer experience.

Wrapping Up

As we wrapped up our conversation, Jason offered his sneakers and website development services. Madeleine expressed her gratitude for being part of the podcast. This conversation was a treasure trove of insights and lessons, emphasizing the importance of partnerships, understanding the customer, and staying connected to the customer as a business grows.

For more podcasts about Customer Experience

Talk-Commerce Leigh Sevin

Bridging the Digital Retail Gap with Leigh Sevin

Remember when shopping, marketing, and brand building were all going digital? Leigh Sevin and Jinesh Shah noticed how little the retail industry had changed its approach to sales. @endearhq

While the rise of online shopping pushed many brands into the next frontier of marketing and customer service, retail salespeople were still confined to the in-store experience. Associates’ limited access to resources and inability to earn credit for online sales highlighted a massive gap in the retail sales model.

We interview Leigh Sevin, the co-founder of Endear. She gives us insight into this ever-changing market and how Endear works to bridge the retail gap.

Endear is the first and only clienteling app certified for Shopify Plus merchants. Its CRM and messaging platform is made especially for retail sales teams and tracks how messages convert into sales in-store and online. Endear empowers retail teams to engage customers over remote channels like email and text. At the same time, the app measures how outreach is performing, including data points like average order value, location of last purchase, and time to convert.

What is a CRM?
What is a CRM?


Brent: Welcome to Talk Commerce. Today I have Leigh seven. She is the co-founder of Endear and Leigh, go ahead and introduce yourself. Tell us your day to day role and maybe one of your passions in life. 

Leigh: Sure. So as you said, I’m the co-founder of Endear. Endear is a CRM designed specifically for consumer brands.

Leigh: So we help brands consolidate all of their data and then empower their sales people to use that data to develop really high quality. Relationships with their customers, primarily over email, texts, and of course face to face. 

Leigh: In the free time, I do have, I also enjoy exercise and baking. 

Brent: Oh, wow. Baking. Good. Are you watching the new series of the great British bakeoff? 

Leigh: I didn’t even know it launched. Has it got, is it alive? Is it, Can I launch? 

Brent: Yeah, I think there’s, there is two episodes out.

Leigh: This is very big news as I go into fall, so thank you for this. 

Brent: Yes, it’ll, it, it’ll be very addictive. Good. And I apologize for cutting you off there. No, not at all. Good. Alright let’s talk about CRMs and if you wanted to just do a brief overview for people who may not know what a CRM is. 

Leigh: Yeah, absolutely.

Leigh: CRM is customer relationship management. So really what that means is, when I’m speaking to maybe someone a little bit older or not as familiar with technology, I really describe it as a really high powered grex. So that’s one way to think about it. It’s about taking everything you know about a customer and putting it into one consolidated place.

Leigh: What Endear does in terms of taking it a step beyond that is Basically we try to give you the insight that data is revealing in the aggregate. For example, specific to consumer brands, those things might be what does a customer’s lifetime spend? What’s their average order value? How often are they shopping with you?

Leigh: And these are the things that one of our users would probably try to do on their own, just from the raw data that they might have. And we just wanna take that work off their plate and give it to them in real time.

Brent: Users who are familiar with a CRM would ask then, as a retailer, why would I need a CRM?

Leigh: So CRMs are incredibly popular for the B2B world, right? There is no technical or technology sales person that would spend a day not logging into a CRM. And I think what’s changed about retail, especially for the sales people, is that they used to be able to readily depend on organic foot traffic and therefore not need to do a lot of outbound sales.

Leigh: What came their way was enough to reach their goals and really succeed as a salesperson in a store, atmosphere. But I think what’s changed, especially with eCommerce and obviously with the pandemic and just generally with how much is available to consumers these days, you do need to stand out.

Leigh: You do need to take matters into your own hands, and that’s really what CRMs are there help a salesperson do. It’s about understanding who can I be reaching out to proactively in order to generate a sale, generate a relationship, understand what their needs are, share updates with them, and that all comes from being able to combine the actual data that we’ve consolidated for you with scalable outreach and tracking.

Leigh: So understanding. If I do reach out to this person, how are they responding to that outreach? Are they opening my message? Are they clicking on the products I’m recommending? And I think the insights aspect of endear is what really keeps people motivated to know that, Hey, my, my text message actually converted into a sale.

Leigh: Maybe that customer didn’t come into the store to do that, but that shouldn’t matter. What matters is my efforts led to revenue for the company. 

Brent: From a differentiation standpoint do you think Endear makes itself from other platforms that are strictly e-commerce? 

Leigh: I would say, when we think about CRM, Omnichannel versus e-com, most of the time CRM is genuinely lacking on the e-commerce side as well.

Leigh: But for the most part, e-com brands tend to compensate by relying on individual departments stand in for CRM. So for marketing teams, a lot of the time that’s their email marketing platform or their SMS marketing platform for support teams. That might be their live chat, right? It’s everyone that’s ever asked them a question over live chat.

Leigh: Maybe there’s a customer profile, maybe there’s not. And to be honest, for us, CRM is just so much of a low hanging fruit in the sales world, and also the department that is right now least saturated with technology, they have really nothing but the terminal. So we wanted to go where the pain was most heavily felt, and that to us was sales.

Leigh: But I would say CRM in general tends to be more oriented towards B2B salespeople, and that’s really where Endear differentiates itself. We are more about the integrations that a consumer brand would need, the KPIs that a consumer brand would need, and the amount of data storage that a consumer brand would need over what a B2B brand or company would need. 

Brent: When I, as a user come into a retail store and endear is being used there, is there a way that the user would target me or help understand more about me? 

Leigh: It’s a, That’s a checkout. Yeah, I get that question. Did you say after checkout?

Brent: No. During checkout or 

Leigh: before or whatever. So I get, if you already know the person time and the funniest part is that question assumes something that you’ve already decided to walk into a store. And actually for retail stores, the hardest part is getting you to do that. Stores for better or worse, actually have an incredibly high conversion rate.

Leigh: The convert, about 30% of the people that walk. The return rate is also dramatically lower than it is on econ, right? Econ faces at this point, probably near 40% return rate, whereas stores probably having the single digits. So you know the, What we have to think about is where is the challenge? Is the challenge, knowing who a customer is once they walk in.

Leigh: Not really. The store does great. So to us, the real pain point is how do I get you to walk in the first place? And that’s why Endear is so much more about what to do with your downtime, what to do to generate foot traffic or generate converting traffic on your website. And that to us comes from really understanding who your customer is, cultivating that relationship, and then extending that relationship beyond face to remote channels like email and text.

Brent: Do you leverage social media and allow the users to leverage some of that social media as well to promote that drive to get people into the. 

Leigh: I would say that’s something that we’ve considered and have on our roadmap for later down the line. I think there are incredible conversations going on over Instagram right now, where we see Endear coming in most often for social media is we have this really cool feature called stories.

Leigh: And they’re basically, depending on your platform, they’re completely shop. So it basically allows for salespeople to create a custom or completely, special story just for one customer or a group of customers, and send it only to them. And that’s something that they can share via a simple URL that endear then tracks for you.

Leigh: So we do allow some flexibility over how you’re using some of the assets you’re creating within endear across platforms. But really what we’re after is that really high touch, one to one conversations. 

Brent: And you’re looking for customers to repeat at the store and increase that traffic from their existing base, right?

Leigh: Yes. We are only using a, the data that a brand already owns, but we’re making them do more with it. So the, KPIs that we focus on helping a brand improve is how do I extend lifetime value? How do I increase aov, how do I increase loyalty? What most of these brands are dealing with right now is incredibly high customer cost of acquisition.

Leigh: And so the only way to compensate beyond just simply trying to reduce that, which I would say you can do by opening a store in the first place, is by then increasing the lifetime value. And that’s really what Endear is 

Brent: all about. Do you see, so you mentioned lifetime value. Do you think that the stores that leverage an online.

Brent: can mix and matched both to get people online and then offline to purchase things as well. Do you see that as part of the puzzle and gaining traffic for the retailer? 

Leigh: Yeah, absolutely. There’s a very famous stat sort of floating in the ether that opening a store basically increases your eCommerce traffic by about 37.

Leigh: What a lot of people miss is that they’re talking about traffic. So that’s an easy number to gauge. I think what our customers want to know is what about actual conversions? And that is really where your sales people are such a great resource for not just, working, as I said, face to face, but then motivating customers when they go to buy online, to feel more confident about their purchase, to buy more frequently, and also probably decrease the return rate.

Leigh: They really do know what size they are. They know maybe they’ve actually tried it in store and then only got really convinced to buy it after the fact. But those purchases tend to be a lot stickier than the ones of a customer just shopping on their own. And we’ve actually seen that in our own data that customers who shop with the help of a salesperson, even online actually in one case study, had a 50% higher AOV than the customers who were going at it alone.

Brent: Have you seen a difference pre pandemic to post pandemic on challenges that retailers are facing and getting people into the store? Obviously during pandemic it was impossible to get ’em into the store, but you see a switch in how behavior is now, whereas we’re going into full opening . 

Leigh: I think, this sort of ebbs and flows because I think what also happened was Every retailer that was a little resistant to change.

Leigh: Maybe they started brick and mortar, really had to open eCommerce and had to embrace that as a channel during the pandemic. So if anything, eCommerce has gotten way more competitive because anyone who was resistant before now needed to figure it out. And obviously their first move is to do all the most obvious channels.

Leigh: That used to be the reason why e-commerce was so great, you could acquire customers for, not much money compared to the cost of opening a store. And I think those two levers have now completely switched. It’s become actually dramatically more affordable to open a store these days because landlords had to learn 10 year leases are not gonna work, no one’s gonna sign a 10 year lease.

Leigh: And we saw that a little bit with the popup craze. And I think that has found its middle ground of saying, what does a two year lease look like? Is that better for me? How can I make it more appealing for tenants to come into my physical space? So those costs have dramatically dropped while the cost of doing business online has actually skyrocketed because everyone’s using the same tools, everyone’s using the same, acquisition strategies.

Leigh: So it’s really hard to stand out right now online. 

Brent: Do you see Paid and organic traffic coming to a store, be it online or in person. Do you see any way that somebody could jump start coming into the store rather than if you just didn’t wanna do paid ads? Is there an advantage somebody has to do organic?

Leigh: I think endear is that organic opportunity. We always joke that a marketing team at a omnichannel brand has so much work on their plate, and they are primarily worried about traffic to the site, conversion on the site, and it’s just not, if you have 12 stores right? That means that they can’t be focused on making sure every single store is optimized or maximizing their opportunity with traffic.

Leigh: So really what you get is you have this huge database of customers and the people who are. Focus on making sure those customers know about the store is the store team themselves. So giving them the power within Deere to actually do their own local marketing, their own local outreach. They are going to be the most motivated to get those customers in the door.

Leigh: And I think that’s really, that’s free. You have to pay for a sales force, whether you like it or not, if you’re gonna open a store. So you might as well maximize their resources to get that ROI on that physical retail. 

Brent: Yesterday my podcast was about segmentation and and the person that I had on had mentioned Klaviyo. I know that there, there’s a lot of overlaps from CRM to automated marketing. How do you work with other partners to ensure that you’re maximizing? If somebody has attentive or something, how do you work in Totally making sure that. both are being used effectively.

Leigh: That gets to the whole purpose of CRM. We did an analysis at one point, and I think about 75% of our customers use Klaviyo, and I think another like 40% also use Attentive. And so what that tells us is, A) there’s this thing that we call called the Commerce Stack, and just to even be a proper eCommerce brand, you need about seven different apps cuz you need your email marketing and or SMS marketing.

Leigh: You need your loyalty, you need your support, you need your onsite popups and engagement. And then you also actually need the os, the backbone of the whole thing, which is typically Shopify. So With all these different platforms running, they’re all really good at what they do individually.

Leigh: The question. How do you bring them together from a data perspective? And that’s really what a CRM is out to solve. It’s how do you understand, okay, who is my marketing team touching with Klaviyo and who is my sales team reaching out to via Endear?

Leigh: And Endear works to actually consolidate those two things so that you understand, who’s responding more to one channel or another. And across all these channels, what kind of picture can I get of this customer? What kind of marketing does she respond to? What kind of email does she respond to or text?

Leigh: Does she respond to? Has she used her loyalty points? How do we get her to use those loyalty points? So all of it is about actually using these apps in tandem. And then of course, I think right now people are very concerned with, their overall spend on technology. And so the next question has to be,

Leigh: how can I consolidate how many of these apps actually have overlapping functionality? And I think that’s gonna be the really big challenge that comes next For these e eCom brands or for these omnichannel brands, how do I really make sure that I’m being most efficient with the tech stack that I’ve created?

Brent: Do you see a future in SMS verses email or both? Or? I see SMS happening a lot more, but I also see a lot of now, spam and SMS. Do you see SMS moving forward in what where it’s at? Or do you see it plateauing soon and people are gonna ignore messages in the future? 

Leigh: It’s gonna take, it’s not there yet, but it’s gonna take the same toll as email, which is, would I ever not answer an email from a friend just because of how much email marketing I get?

Leigh: No. It doesn’t stop me from finding the ones that are important and of. All of our personal email clients or our phones will help us do some of that filtering automatically. So I think what really it comes down to is what is a brand’s email marketing or SMS marketing strategy. And I think the challenge there is that is also why empowering a sales force of some sort can be truly needle moving.

Leigh: They will break through the numbness that comes with marketing at some point. If I truly know somebody and they’re texting me, I want to respond because they likely, the content of that message is personalized. It’s specific to me, It’s content that I care about.

Leigh: And so it’s just about, everyone will say it, but it really is about personalization. And I think what’s cool about focusing on sales rather than marketing. , it lets you not worry so much about scale. The whole point is it doesn’t have to be all that scalable because you have a huge labor force, you have a huge sales force, so let them just do it properly one to one, and it will convert really high.

Leigh: And if you have 20 to 50 people doing that, you’re gonna see incredible results. And as I said, those people work for you anyway, so why not let them cut through the noise? 

Brent: Do you think that the big brands out there that are running retail stores, The challenge is getting people into the stores again, or what do you see as the biggest challenge facing retail today?

Leigh: I think from a growth perspective, it is probably that, you still need to figure out how to drive traffic to your stores if you’ve made that investment. I think the other challenge is still for a lot of brands, especially the big ones, omnichannel, How do I understand? How my online and offline channels are working together.

Leigh: How do I make them work better together? How do I help them be resources and allies talk to each other? Because a lot of the time when we at least launched Endear, there was incredible sort of antagonism between what was happening e-commerce and what was happening in store, and they were considered almost rivals.

Leigh: And I think that is one of the biggest mistakes that a brand can make. It’s more about how can these two channels support each other. I think there are really great examples. , brands that have done that really well. With online, with in-store pickup for online purchases, making sure you can return, something you bought online in a store because A, that drives traffic and b, that’s just logical.

Leigh: Not doing that is gonna really annoy your customers. And so for me it’s looking at the strategies that actually unify those things. One of my favorite sites actually does this very cool thing where you can actually search their website by what’s available local to you. So you can basically browse the store from their e-commerce site and then just go buy it or go reserve it, which, talk about same day delivery.

Leigh: You don’t even need that. You can just walk over and go get it. 

Brent: Looking at somebody like Best Buy, certainly they’ve now embraced that. It took ’em a a little bit of time to get there. But you can obviously that features a great way to make sure that people see everything, but then go to the right place to get it.

Brent: The future of. I think it was interesting that Amazon is still opening physical stores today, so it’s like online to physical. Do you still see that happening? Do you think there’s gonna be some strictly e eCommerce brands that are going to do little popup stores to see to see how it works?

Leigh: I think there are different, physical presence formats that are right for different kinds of products. And I think what we’ve really seen over the past couple of years is innovation around what does it mean to have a physical presence, right? It used to be a question of do I do wholesale or do I do retail, like dedicated retail?

Leigh: And even that’s a relatively new concept. So what I love is looking at all these different models for how brands can test what it means to. available in a store, whether it’s their own store or, these new sort of neighborhood goods is a great example, right? It’s not necessarily a wholesale deal, it’s more like I’m leasing or renting shelf space rather than an entire, store.

Leigh: And so all these different models allow different kinds of companies to really test what makes the most sense for them. And I think, the same time that Amazon is opening. Warby Parker is still opening tons of stores and actually doubling down on their retail footprint. So I think if anything, it’s a sign that, physical can work for all different kinds of companies and it’s more about understanding and really testing what makes sense for you, and how do you collaborate with other brands so that you are maybe doing a joint effort and you’re not, taking on the entire cost of leads for yourself if you happen to be at a one type of product or one product business that’s not really gonna make sense to just populate an entire store with one product? 

Brent: Yeah. I think if anything, the pandemic reminded us that we do like to go outside every once in a while and visit a store and touch a product and shop around and visit, just get out of the house.

Brent: Do you do you think that a lot of retailers now are moving towards Having something like Endear to help them leverage more of their in store versus versus web traffic to promote specific items. You talked about the one item thing, but is there more of an in, in if you have Overstock or under stock, is there a way, is there more of a push to get a lot of that stuff?

Brent: I know there’s a lot of Target has a ton of extra inventory. So they’re pushing, this inventory online, offline. Is there more of that now coming through on retail? 

Leigh: Yes, and I think inventory, especially if your omni channel is one of the hardest nets to crack, and it can get very cumbersome and it’s very detail oriented, very logistics heavy.

Leigh: And that to me is another reason why stores really do benefit when they have something like Endear because they have those products literally right in front of them. And with Endear, they can know exactly who. By the store and who would be interested in this product. So being able to again, be your own best advocate and move product that may even be sold out online.

Leigh: Being able to tell an entire neighborhood, Hey, that thing that’s sold out online is actually available in store in your size, come by and hopefully be the first to get editor. I can reserve it for you, is an incredibly, a huge value prop to your community, but also a really easy optimization considering all the challenges that brands face with inventory so it’s basically taking advantage again of your human capital to solve a very big logistical challenge. And I think, best sellers are always gonna move, and that’s great, but especially if you have those lingering products, being able to target them also without even broadcasting necessarily a huge promotion via a marketing email, Potentially sending it to only a handful of VIP customers or a handful of customers who have bought something similar in the past and just extending a promotion to them.

Leigh: Also helps, this long history of the vicious cycle of, if I discount then everyone’s gonna wait for the discount that if I don’t discount, it’s never gonna move. So avoiding that major sale and just giving a handful of people maybe part again, like you have a loyalty program for a reason.

Leigh: You know, Show your gratitude to those people and give them first access, or give them last access to some of these lingering products is a very easy way to really make the most of the inventory you do have. 

Brent: I wanna change gears a little bit and talk about entrepreneurship. What motivated you in your young years to start a new CRM?

Brent: It’s a very competitive space. Tell us your journey on Endear and starting that. 

Leigh: Yeah. My co-founder, Jenesh and I really got into this space pretty circuitously, it was not a very linear path towards success, but what we landed on was quickly learning that within the physical space in retail technology was lacking.

Leigh: There was a huge doth in just any sort of innovation whatsoever. And of course what we saw was this boom in econ technology and it made sense, right? It’s already cloud based. It’s already driven by fast movers. People who were excited about the future in retail to a lot of people sounded like this very laggard, slow industry that would never adopt anything new.

Leigh: And I think that was one of the biggest misconceptions because if there’s huge success in econ, obviously retail stores are eventually gonna have to. And so what we saw was this huge white space, especially among the newer, more modern brands who were leaning on physical retail as a new growth channel.

Leigh: And they were so data oriented already, and there were no solutions in the market that sort of looked at what the store was doing as a CRM. I think it. Maybe our exposure as solving this problem for our customers, but also ourselves needing a CRM and having a sales team that we realized they were really one and the same.

Leigh: They were all facing the same problems. And I think it’s our orientation towards data specifically that really sets us apart in the market because we’re just giving our users much more information and ammo to work with. Compared to just letting them, maybe you just have a messaging platform. That messaging platform is only as good as the content that the users are sharing on it.

Leigh: And so I just think that relying only on something that lets you do SMS is never gonna get you the scale or the quality of conversion. That’s something like Endear would. That was the biggest lesson, was getting to talk to users and understanding how much of their business was already driven by cultivating these relationships.

Leigh: Understanding that this behavior already existed. It’s just that no one had really, hypercharged it, No one had really given it the proper attention from a tech perspective that it deserved. 

Brent: When you started what was your biggest challenge at getting up off the ground?

Leigh: I would say our biggest challenge was really accepting. Being willing to focus on who it was that needed our product most. I think for a while, and I think it’s normal to go through this, we would take any customer that would have us and we would, do whatever they asked of us. But slowly we realized that, there needed to be a very concrete market that we were going after and we needed to use the customer experiences we already had to pinpoint.

Leigh: Exactly who that customer should be. And I think in almost every conversation with a new founder, every conversation, every interview I give, I talk so much about product market fit because I think it is the hardest part of starting a company is finding the product that satisfies a market doesn’t, worry about how big or how small it is, maybe later.

Leigh: But just building something that an entire audience loves is incredibly gratifying and motivating. And being willing to settle on one audience was something that is really hard for founders. 

Brent: Do you think that it’s hard to say no to some customers sometime or even say to that customer, you’re really not a good fit and maybe you’re not gonna be successful with us, so why don’t you use X platform?

Brent: We have problem 

Leigh: now. We. Can’t help ourselves from time to time. It’s very tempting when someone wants to use your product and you have to be honest about what it can do for their business or what you’re willing to do to meet them halfway. And I think there’s a saying basically that most startups die of congestion, not starvation.

Leigh: And I think that’s a really good way to think about it, especially at where we are in the seed stage. You have to be able to focus and you have to know why you’re focused. And I think it’s always good to put opportunities on your own radar for investigation and research. But we’re always remembering, your bread and butter customer and why they love you so much because they are the ones that will keep feeding you.

Brent: I’m gonna make a small CRM joke, so I apologize, but when you were looking at how you were gonna design Endear, did you look at SalesForce CRM and think , this 1980s interface is the last thing I’m ever gonna want to do, and we’re gonna make all this great data presentable for people who can actually use it.

Brent: and if anybody’s used Salesforce CRM, they know exactly what I’m talking about. 

Leigh: I have to be completely honest, I’ve never seen the Salesforce CRM. I don’t know what it looks like. All right. But you’re very lucky. I’ve heard that, I’ve heard that from so many people. There’s like a I literally think there’s a quote on our website that is basically we have plenty of users who have tried Salesforce and to even think about putting.

Leigh: A retail worker who’s constantly on her feet on Salesforce to use as if she were at a computer all day is absolutely insane. And so we’re very honest about, the way that we’ve built the product, specifically for someone who works in a retail environment, someone who is able to, they have to be able to look up from their phone no matter what they were doing, and work with a customer and then look back at their phone and know exactly where they are in their workflow and pick it up instantly.

Leigh: It’s not no secret that turnover is also incredibly high in retail. And so what we think about in terms of how we build the product is okay, and there needs to be something that the second you hire a salesperson, they can pick it up in 30 minutes. They do not have six months to train on something like Salesforce because they’ll probably be gone in six months.

Leigh: So how do we build something that, A, they can get up and running in 30 minutes and B actually might get them to stay longer because they love the tech. They love that they can track their own progress. They love they get credit for sales online. So how do we make it a reason for someone to actually stick with your brand because of how great, the motivation is through Endear.

Brent: Do you find it harder to. design, something that’s easy for a millennial to use as compared to somebody who’s retired but now has gone back to work and is suddenly in retail. Do you think there’s a challenge in both in that sort of learning phase? 

Leigh: So one of our first customers, they actually were a beta customer and they were still with us today, like three years later, they got a version of Endear that we would never want anyone to have to be on.

Leigh: The entire sales course were in like the boomer generation, and I trained every single one of them. Maybe sometimes it took an hour and a half. But what I knew was their willingness to work with me and to get trained and then their ability to use the platform was probably the biggest validation that we were doing something worthwhile because every single one of them got on and said, I absolutely hate technology.

Leigh: I don’t know why we have to use this, and yet somehow three years later here, they are still using it and getting even better at it, and they are incredibly productive. So to be honest, millennials are great at tech and it’s great that they use Endear and they, I think they love it. I think what’s more encouraging is that we have users across all generations and they all seem incredible value.

Leigh: And getting up to speed and actually, finding it pretty easy to use at the end of the day. 

Brent: And I can say that I’m old enough to remember when I was working as a waiter that you had to look through a big book to see if this credit card was stolen or not. So it has come a long ways.

Brent: Another good parallel would. Somebody who’s a runner and they log all their miles in a physical book and then they move to a spreadsheet, and now they’ve moved to logging all their miles in Garmin or Strava or something like that. Strava. So that same sort of pathway for the CRM could be seen through how we’re making our lives easier.

Brent: And you don’t have to at checkout or at at the pos or even as somebody walks in there is an opportunity or getting people to walk in, I should say. There’s an opportunity to somewhat know the customer and then to leverage that knowledge to help them understand that there’s something.

Leigh: Totally. I tell every founder, if you ever hear of an industry still relying on Google Sheets, that is the billion dollar idea to go after. It’s always a sign that there’s a problem to be solved. And I know a lot of companies that, they are the Google Sheets alternative. They are, as you’re saying, the Strava to just logging it in a Google sheet or same for us, our users went from little black books to, if they were relatively sophisticated, A, a pretty, color coded Google file and then they found us.

Brent: The the typical customer that you would see or the typical user for Endear, would there be a certain size that would be a right fit? 10 stores, 20 stores? 

Leigh: We, when we started, a lot of our customers were smaller. I think more of a mindset. Certainly from a, traditional icp.

Leigh: What are your qualifiers? What do you look for? We look for brands that have, north of three stores. That’s something that we do take into consideration mostly because it shows a level of bullishness on physical retail and eagerness to. We look at their tech stack. Do they use platforms that we already integrate with that we, so that we can deliver that really 360 degree view of the customer?

Leigh: But I think what we’re really excited about that we’re seeing now is, if you did start with Endear when you were relatively small, there is no interest in moving to Salesforce because it’s just, it doesn’t matter how big you are, that product is still not designed for the retail store enviroment.

Leigh: And so we’ve seen customers that, started in the single digits that are now, double and nearing triple digits store fleets. And they are not giving us any signs that they’re interested in leaving because we’re growing with them and we are watching their needs change and become more sophisticated at the same time that the product becomes more sophisticated.

Leigh: We obviously hope that trend sticks around, but that’s what we’ve seen so far. 

Brent: I’m doing a terrible job of staying on track here, but if we jump back to entrepreneurship have you found it harder scaling your tech stack or your people stack? 

Leigh: That’s a really good question for my co-founder Jinesh and our CTO JP, but I will answer it as best as I can.

Leigh: I would say people stack on some level proves to be more slippery in the sense that I think you know what you’re getting with tech and if you don’t know, you’ll figure it out pretty quickly and you are even aware of the quote unquote like tech debt that you might be taking on at any given moment.

Leigh: And it’s also probably pretty clear to you how to fix it. I think the team growth side is you have all these things that you want to, that you wanna do or that you wanna think about, and finding that balance between hard skills and culture and also, equity and making sure that you’re finding that diversity in the applicant pool that you’re looking at.

Leigh: And then you have to think about we are a distributed team. Do we always wanna be distributed? I think so. What are the drawbacks and what are the advantages of that? And what if there are drawbacks, how do we compensate for those? So I think there are just a lot more unknowns when you’re dealing with humans in general, which is why, tech products are really fun to build.

Leigh: because you can rely on them, but then you realize like there’s a user at the other end of that and you have to think about, how are they going to receive this product? What are they gonna want to see from it? So I’ve just basically bundled your questions still back into endear and the problems that we have on that front.

Leigh: But I would, I hope I answered it at some level. 

Brent: When Leigh wakes up in the morning, what drives her to get up and do something better? Stronger. Bolder as the Endear co-founder. 

Leigh: Anecdotally and broadly, I would say it’s the customers that we work with.

Leigh: So I absolutely adore this space. I love the customers that I work with. I geek out when I see a brand that I recently shopped at or know or just follow on Instagram, and I see them wanting to use in Endear. And I feel the same way when one of those customers just has an amazing experience or one of their sales people has an amazing experience.

Leigh: And knowing that, as I said, it goes back to product market fit, you get incredible motivation knowing that, hey, even if something is broken, even if you know an employee wants to leave, all of that stuff is totally solvable if your customers love your product and it’s totally worth solving if your customers love your product.

Leigh: I wouldn’t feel the same way if customers didn’t. It’s like, why are you even bothering? Like you have a bigger existential problem if your customers are not huge fans of what you do every day. 

Brent: Do you ever buy something from a store that’s using Endear and you wanna say, That’s my product you’re using?

Brent: Yes, all the time. The person that’s selling it , by the way, that’s my product. Yeah. 

Leigh: I’ve done it. I’ve done it a few times. I also have a very. Supportive husband who won’t walk into a store that doesn’t use Endear without trying to pitch them on endear, which I also appreciate, but I have also stopped doing.

Leigh: It’s very cool to walk around a lot of neighborhoods in New York and see the brands that we work with. I’ve walked in and it’s just a weird interaction. You’re like, Oh, that’s cool, thanks. But it’s not quite anything, I think it would be pretty weird.

Leigh: A HubSpot person came up to me and was like, I work no, actually I’d appreciate it. I’d be like, That’s cool. We use HubSpot. So I try to keep my cool when that happened. But I would say the other thing that gets me up in the morning is when I have friends who say, I just got a text from a store using you and I, I saw you in the url, or I could tell it was you guys.

Leigh: And I think that is also incredibly inspiring that, we are. Penetrating all these different circles of people that are receiving her product and most of the time not even knowing it.

Brent: I started in the Magento world, which is like Shopify, but it. It’s better. And it’s, No, I’m just, I’m not gonna talk about that. But I can also relate to that. Nobody actually cared at all that I was using Magento to sell stuff or developing on Magento. Anyways, we’ll move on. We have a few minutes left.

Brent: And I promised a free joke. I was gonna do it in the beginning, but then I forgot. And now we’re, because I’m a d today, I don’t know why. So I’m gonna tell you a joke. And this is a joke that could be free or we could pay for, . All I want you to do is just react and tell me what you think.

Brent: Here we go. 

Brent: Two fish swim into a concrete wall. One turns the other and says, Dam!, 

Leigh: Okay, 

Brent: I’m, make it, I’m, That’s clearly a free joke. I’m gonna say a free 

Leigh: joke. I was actually ready for it to be. A different punchline from a different joke, and I was like, Maybe this is a different version. So you actually caught, 

Brent: Tell me yours.

Brent: Tell me yours. You know 

Leigh: The one where it’s like there are two muffins baking in an oven, and one muffin says, Damn, it’s hot in here. And the other one says, Oh my god, A talking muffin. So I thought that was gonna be the joke, but with two fish , 

Brent: Yeah. How do fish talk underwater? That’s my question. It’s Aquaman, right? They must use some kind of radar thing.

Leigh: Yes. And there’s that very famous David Foster Wallace speech or short story about what is water? And it’s basically like people’s awareness. If you haven’t, that’s also what’s on my mind now, which is, it’s a much more existential philosophical question.

Leigh: So now I’m just in 10 different places like you, so there you go. 

Brent: All right. I gotta do one more since I clearly bombed the first joke. 

Brent: What is the opposite of a croissant? A happy uncle.

Brent: Okay. Cross an, Yeah. Anyway. I get it. I will stop torching you on the jokes, . I 

Leigh: appreciate them.

Leigh: I get it. I’m with you. 

Brent: If you were to say to a retailer the thing that they should be paying attention to as we go into Black Friday, Cyber Monday. What would be that something they should be really looking at now, going to quarter four and even into quarter one?

Leigh: That’s a great question. I would say, what are you gonna do differently from last year? And ask yourself, what did I do last year? and what have I done every year that, am I seeing any difference in results? And I think the question becomes, if everyone else is just gonna do the same thing anyway, what is the harm in taking a year to try something that I’ve never done before?

Leigh: And at the end of the day, I’m not a retailer. I only have so many creative ideas that I’ve seen from the brands that use us, but I think. A like getting ahead of the most obvious things. Like you’re gonna send a promotional email the week before and then three days before and then the day of your sale.

Leigh: What doesn’t look like that? Just anything. But that is my advice at this point, because you can always do that. But is there something more creative you can do either on top of that or instead of that, because you know everyone’s gonna do that and we do have that. Have test.

Leigh: We do have an entire webinar from a bunch of other brands speaking about this that I would highly recommend. This doesn’t count as my shameless plug. I wanna clarify that. I would recommend people go listen to if they’re looking for inspiration. 

Brent: All right. And we’ll put that in the show notes. So we’ll make sure you get that on the show notes of the podcast.

Brent: So Leigh, as we close out, I give everybody a chance to do a shameless plug. What would you like to plug today? 

Leigh: I would like to plug Endear as an app, is that allowed? Can I just plug the company? Absolutely. Okay, great. Yes, one of the great things about Endear sales process is we offer everyone, both we can get a demo on the app and then we also include a free training as part of your trial.

Leigh: So I would encourage everyone to a go check out the website and and book a demo because there are no strings attached. And you’ll even get a free training if you sign up for a 14 day free trial. So that is my shameless plug. 

Brent: Perfect. Leigh Sevin co-founder of Endear. Thank you so much for being here today.

Brent: Thanks so much. Had a 


Leigh: time.

What is a CRM and Why do You Need One?
What is a CRM and Why do You Need One?