How The Yes Built the Best Shopping Experience in Fashion


In this Gladly podcast episode, join founder & CEO of The Yes, Julie Borstein, as she shares the story of her brand’s rise to become the best recommendation engine in fashion, plus how customer service fits her mission to always make the answer, “yes.”

Hear how years spent innovating at brands like Nordstrom and Sephora guided Bornstein’s lifelong passion to create the best personalized shopping experiences.

“It’s all about how you get to the yes and make the customer happy.  That is a deep belief of mine ”

Julie Bornstein

Co-founder and CEO, The Yes

Joseph: Welcome to the Radically Personal podcast where the people behind the most beloved brands share how they put their customer at the heart of everything they do. I’m Joseph Ansanelli, CEO of Gladly. On today’s episode, we sit down with Julie Bornstein. Julie is ...

Joseph: Welcome to the Radically Personal podcast where the people behind the most beloved brands share how they put their customer at the heart of everything they do. I’m Joseph Ansanelli, CEO of Gladly. On today’s episode, we sit down with Julie Bornstein. Julie is the co-founder and CEO of The Yes, a new service designed from the ground up for the ultimate personalized shopping experience. Julie has been at the forefront of eCommerce and powerhouse brands like Nordstrom, Urban Outfitters, Sephora and Stitch Fix, now at The Yes, she’s working with an amazing team, creating the best shopping experience in fashion.

Julie: My idea is, how do you build a store for each user that is understanding of the things they like and what matters to them?

Joseph: And we’ll find out how the name The Yes is driving this strategy of customer service.

Julie: It’s all about how do you get to yes and how do you make the customer happy.

Joseph: And lastly, we’ll hear about a radically personal story and how Julie has always been a rule breaker and how she expects no less from her team.

Julie: And I don’t really want our agents over time having rules. I want them to have the tools to do whatever’s right for the customer.

Joseph: This is Radically Personal.

Joseph: I am so excited to have you, Julie, on today and to be recording this together. Why don’t you tell us a little about you and who you are so that everyone has that background?

Julie: So I grew up in Syracuse, New York, and it was a really cold, boring place to grow up and so I spent a lot of weekends in the mall and I was always really interested in shopping. It was sort of my personal hobby and I was very good at it and I knew what I wanted to see oftentimes before the product hit the stores, I thought I wanted to be a fashion designer when I was young and I would sketch, but turns out I’m not that good at sketching.

Julie: And so as I grew up, sort of went on to college, I would say I was graduating and my friends were becoming, sort of going to med school and going to law school, and I really wanted to do something in business and fashion and I didn’t know what that meant or how to get into it, but I knew that was an interest. So I moved to New York city, got a summer job at a law firm after graduation and basically pounded the pavement and wrote letters, this is pre-internet, to whom it may concern at Ralph Lauren, Donna Karan and Calvin Klein, the three of major fashion brands in 1992. And ended up getting ignored by two, getting a job at one and starting my career at Donna Karan.

Julie: I then went on to do a few different things, came back around, went to business school, worked in investment banking with retail and consumer companies and realized that I was really interested in the retail side of the business. And so I moved up to Seattle and went to work for Starbucks primarily because it was the most interesting dynamic retailer at the time. I had just worked on the sale of a coffee company and so I met Howard Schultz at an event and convinced him to hire me, basically. Once there, really the internet started to, I would say, become a much bigger part of everyone’s lives, and my brain just couldn’t stop thinking about the intersection between fashion and online shopping and I had a million ideas. And then about a year after Nordstrom announced they were going to launch e-commerce, they were taking their catalog division and spinning it out. And I spent five years at and loved it and loved the chance to really sort of have this amazing brand built over a hundred years and helping to sort of build what was e-commerce for them.

Julie: And as a brand, the thing I would say I learned from it is if you put the customer first, you always win because at least your heart is in the right place. And even if you mess up, the customer feels the fact that you tried and you’re going to make it better.

Julie: Spent five years there, helped grow the business to $350 million, which from nothing, which at the time was big business, and then ended up getting recruited and going to Philadelphia to work for Urban Outfitters and help them build out e-commerce, which was really fun in a really different culture and company, which was what I was looking for and a very, very unique company instead of brands. Was there for two years, Sephora called, they were looking to really build out e-commerce and launch a loyalty program, and the combination of both the role and my family’s desire to get back to the West coast led me to join Sephora. I think that that was where I really learned how to combine sort of my instinct around what consumers needed to help them over the hurdle of buying online. I was there for about eight and a half years and really helped the company make sure that as an innovator in the retail space that Sephora was coming to the US in the late 90s, we would make sure that our online and digital presence was also not just innovative but really leading edge.

Julie: And while I was there I was introduced to Katrina Lake, the founder of Stitch Fix and fell in love with that business and with all the things that she was doing and joined her board. And then a couple of years into that as an investor and board member, was very compelled by all that was happening there and so I joined Stitch Fix full time as the COO. And Stitch Fix was … I mean, there were two big things really for me that were great about that experience and I knew going into it would help me definitively decide if I wanted to start a business, which was always something I’d wanted to do. And I’d say the first was just working in a startup environment, working with venture investors and seeing how quickly we could move in those early days by not having the constraints of a larger organization with lots of legacy things. And so it really gave me the excitement behind the pace-

Joseph: Entrepreneurship.

Julie: Yeah. And then the second piece was just the work with Eric Olson and the AI team, the data science team, as we called it there, and really starting to understand how data could not just be used to analyze sales and customer behavior after the fact, but how it can be used as a tool to power sort of the user experience. And so in the case of Stitch Fix, the way the whole system was set up, we had algorithms that were scoring product that would then be shown to stylists who could then decide what to select for the customer.

Julie: The big insight for me was I loved working on the tools for the stylists because really what I love is working on shopping experiences. I also really saw this opportunity of if you’re working directly with a customer, the way that you could build on top of AI could be even more different and next level. And so I was on the board for two and a half years, as the COO for two and a half years, and then left at the end of 2017 to start this next project. And so I’m now the co-founder and CEO of The Yes, which has been incredibly exciting and fun and we’re on the brink of launching. We’ve spent two years building this sort of very complex system with a very simple user experience that we’re really excited to launch.

Joseph: Every company has an origin story and I loved hearing the idea behind The Yes.

Julie: The big idea behind The Yes is that online shopping has really remained the same since the very beginning and it’s very overwhelming. It’s really not taking advantage of the technology that exists today. All of e-commerce was built on this infrastructure that was built in the late 90s, it was really modeled after you build a catalog, you merchandise the store-

Joseph: the mail order catalogs that people mailed and put them on the web.

Julie: Exactly. And then good luck to you, go find what you’re looking for. Search sort of works, but not really well. Really you come back and pretty much every time you come back you’re starting from scratch. And so my idea is, how do you build a store for each user that is understanding of the things they like and what matters to them and don’t make me as a user have to sort through and figure out what’s right for me, helps surface that for me once you understand what you need to know about me? So that’s what we’re building. We’re building basically the technical infrastructure to create a customized store around each person. My co-founder is Amit Aggarwal, and he’s a brilliant engineer and leader, and I absolutely could not even start this business without him. He’s really challenged me in lots of ways, and I feel very lucky to have met him and be on this journey with him.

Joseph: Let’s talk about the name. I have this belief that naming is only good in hindsight, The Yes, what’s the backstory? Why The Yes?

Julie: I give credit to Anthony Sperduti, who runs a creative agency in New York called mythology. So we gave him all of the goals around the name, and so the goals were positive and expansive, so we’re starting in fashion, someday maybe we’ll go to other categories, then I gave him my list of names and he added one more to it, The Yes. And what we realized was this was perfect because the whole concept behind what we’re building is this is about you and your yes and so you can yes or no everything in the app and we’re helping you get to your yes. And so it really works in that way. It works because it’s optimistic and that’s so much of my view of the world. And we have a fun thing around no, which is no, N-O, helps us get to know you, K-N-O-W, and so it’s not a bad word because it helps us get to your yes.

Joseph: Part of the magic of The Yes is how they do some simple things with some real power behind them.

Julie: It’s an app first, so we’re launching just with an iOS app and then we’ll have a website to follow. And you answer some questions, it’s a little fun, interactive Q&A that looks fairly light from a user perspective, but there was an enormous amount of data that went into determining what to ask. And based on how you answer questions, different next questions emerge. So we’re asking you questions, you’re giving us answers, and then what happens is you have a home feed that’s really catered to you. And so it has topics-

Joseph: All machine driven?

Julie: All machine driven. So the home feed is basically topics, products, and brands and sort of trends that are relevant to you, so everyone has a different home feed. So we’re launching with women’s, and your wife and I could both like camouflage print but the products that she sees and the products that I see would be different based on other sort of aspects that we like. In order to train algorithms to understand fashion, you need to start with really good inputs, and so we have the most extensive taxonomy that exists in fashion. We did lots of competitive looking to understand what other people were using and we went levels deeper than exists in services that are offering similar kinds of tools to companies. That was done through a team of product experts who really understand everything there is to know about fashion, working with machine learning engineers to understand how to use that data.

Julie: We have a fashion director named Taylor Tomasi Hill who’s been in the sort of fashion space her whole career. She started as a fashion editor at W Magazine, she was at Teen Vogue, she was at Marie Claire and she has spent a lot of time with the design community and she is really our, I would say, fashion guru. So she is spending time at shows and with designers and really understanding trends. And so her layer of, here are the important trends that are relevant, is layered on top. So we have this group upfront and this group at the end that are really important human inputs to make sure that the algorithms are working in a very logical way.

Julie: Everything that we’re building is done in combination with brilliant machine learning engineers and deep product and fashion experts. So this sort of partnership between people who understand the category and the industry and the consumer perspective alongside people who understand how to build these sort of learning algorithms has been a big part of how we’ve built what I think is going to be the best recommendation engine in fashion.

Joseph: So you’re doing all this stuff with machine learning and AI and delivering on this very, very personalized shopping experience, how do you think about the customer service experience in that process?

Julie: My feeling about customer service is like the customer’s right and the answer is yes. And I don’t really want our agents over time having rules, I want them to have the tools to do whatever is right for the customer. And whenever I met with a customer service person or any associate of any business where the answer is no because those are the rules, those are the moments where I’m literally the most frustrated. They’re not listening to the reason they’re not understanding the context. There’s no critical thinking in the process. And so it’s all about how do you get to yes and how do you make the customer happy, and that is really a very deeply held belief of mine. I can’t imagine having a set of rules that every person who’s helping our customers has to follow. All they have is one guideline, and as long as they follow that they should be able to take care of the customer. And frankly, that’s not how most customer service departments are set up and it’s not how most tools are built to help enable that.

Joseph: Right, you give them the right tools and you trust them to make the right decisions and you’ve ingrained the culture.

Joseph: So as you’re thinking about growing the team, how are you thinking about recruiting for that, enabling that culture? It’s such an important thing. It’s like you can teach people functional skills, but how are you going to approach recruiting the right talent to deliver that?

Julie: So we’re planning to have a remote workforce.

Joseph: 100%?

Julie: 100%, yeah. And I’ve seen it both ways, I’ve run customer service teams where they’ve been in one location and I think that it’s a tough job. And so I think that to the extent you want to hire people who are independent thinkers and critical thinkers, you need to create a flexible job that gives sort of these intelligent people a reason that they would want to join the company in this role and make sure that it stays motivating for them. So my belief is that the nature of the role and how you structure the role determines the quality of people you can fill. So if you are trying to hire someone who’s going to follow the rules, you don’t really want to get a good thinker because the second they start to question things, they’re going to feel frustrated and want to leave and be unhappy with their job when they can’t satisfy a customer’s needs.

Julie: And so if we create sort of a service mentality where it’s, you’re here to listen, to understand, to make sure we’re getting the feedback on what’s going wrong for the customer, because nothing drives me more crazy than not actually meet the people who are working on the product, not hearing directly from the customer and understanding it. So the pipeline needs to be a big part of what they’re doing, it’s feeding the information back to us and then being able to understand the customer’s need and take care of them. And sometimes it may be give them $100 credit, but oftentimes it’s not. It’s not about the money-

Joseph: Solve my problem.

Julie: Solve my problem, get me this product, get some other product, make sure a gift arrives, whatever it is, make sure I have something to wear. And so I think the job becomes much more interesting and you can hire more critical thinkers, problem solvers and make the job satisfying if they are empowered to solve the problem for the customer. We’re actually just starting the process of thinking about our hiring guide. And I hired an amazing woman, Liz Romano, who I’ve worked with in the past, and she is definitely … I mean, one of the things I love about her is she is such a can do person and she has such a can do attitude and she doesn’t sort of have this sense, like this is how you have to do it. She’s very open to what’s the best way to do this. And she was the one that found us gladly and led us to you. She’s worked in all the tools and the environments enough to know it’s about customer first and that’s how you guys are built, and so it’s not by channel or by ticket, it’s by customer-

Joseph: Radical idea.

Julie: I know, it’s crazy. And so yes, you need the tools to do it, you need the mindset to do it and you need the flexibility. And I am 100% certain that the better service that we’re able to give as a result of our no policy policy, it will pay back in spades so I’m not worried about it.

Joseph: The name of the podcast is Radically Personal so I always ask people about a radically personal thing about them. You said earlier that you’re a rule breaker, what’s a rule you broke that won’t get you into too much trouble for sharing?

Julie: When I was in college-

Joseph: Uh-oh, here we go.

Julie: My family lived in Syracuse, New York, we were on vacation over Christmas break in Florida and we were flying home for New Year’s, and my sister, who was older and had graduated from college, was living in New York city. And so I knew that the plane that we were flying on, which went from Miami to DC, went on to New York city because my sister was flying out in New York city. Me, my other sister and my parents were flying to DC and then changing planes to fly to Syracuse. I had some friends in New York city and that seemed like a much more fun place to spend New Year’s Eve-

Joseph: I know where this is going.

Julie: So I basically decided that I was going to stow away and stay on the plane that was flying from Miami to DC and just be able to go to New York city. So my parents were pretty relaxed people when it came to this kind of thing, so they were like go for it, whatever. And so-

Joseph: Wait, wait, wait, your parents knew that you were stowing away?

Julie: Yes. I stayed on the flight, they switched the flights, then they said okay, you know people are coming on in DC to fly to New York and someone came to my seat, so I just decided I was going to hang out in the back of the plane because I moved like two seats. So I’m just standing in the back of the plane, watching-

Joseph: Waiting for the empty seat.

Julie: Waiting for the empty seat and then … This is pre-9/11 so the screening wasn’t quite as strong and so they said, “All right everyone take your seat, we’re doing a head count”. And I found a seat that was empty and I sat in it and I just crossed my fingers. They did the headcount, they said, “All right, we’re all full. We’re going to close the doors”, and off they flew and I got my sort of free leg to-

Joseph: Oh, so it worked?

Julie: It worked.

Joseph: That’s amazing. That’s a great story. Yeah. Well, thank you. Thank you for spending this time. Thanks for being such a great partner. The Yes. It’s going to be great.

Joseph: Julie, thanks so much for sharing some stories about your tenacious career journey and your radically personal approach to recreating the online shopping experience at The Yes. I’m Joseph Ansanelli, CEO of Gladly. Thanks for listening to this episode of Radically Personal. If you enjoyed the podcast, please be sure to subscribe on Apple, Google podcasts, Spotify, or visit us at We’ll see you next time.

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With a proven track record of building companies that don’t settle for the status quo, Gladly CEO and co-founder Joseph Ansanelli is reinventing customer service to put people back at the heart of it. Joseph is also a Partner at Greylock, focused on investing in enterprise applications.