Q&A with Julie Bornstein, Chief Shopping Officer at Pinterest: Creative, Emerging Technology, and Leadership Passions Merge

Julie Bornstein, Chief Shopping Officer at Pinterest, is a highly regarded veteran in the spaces of digital, marketing, and retail.?Over the course of her career, she’s led innovation efforts within a wide and impressive range of industries, holding positions at Starbucks, Nordstrom, Urban Outfitters, Sephora, and Stitch Fix, along with serving on the boards of Redfin, WW (formerly known as Weight Watchers), and sweetgreen.?The diverse skillset Julie has acquired through her roles, paired with her own personal passions and business ambitions, eventually led to the launch of her very own fashion-ecommerce company, THE YES, and her most recent celebration of its acquisition by Pinterest.

The Brownestone Group’s Tim Boerkoel spoke with Julie to further explore her exceptional career journey, the lessons she’s learned and the “pivots” she’s made along the way, and the unique and compelling vision she has for the future landscape of technology and fashion.

?Timothy Boerkoel (TBB): Your current title with Pinterest is Chief Shopping Officer, how unique! As a fashion lover and avid shopper, did you ever think that would be your title at this point in your career? Describe how your personal passions - and I recall you also enjoy running, design, film and politics – have complemented your career and influenced your leadership style?

Julie Bornstein (JB): Since I was very young, I have always loved fashion and design. I remember thinking in the 80’s that Gloria Vanderbilt was “it” and she had an amazing career. I actually knew very little about her, but I loved the idea of her. As I got older and understood the business world a little more, my goal was to become a CEO of a retail business. Then it seemed the whole world changed, and technology emerged, which wasn’t something I’d predicted as a kid. What is interesting to me now is that the dream job I envisioned was really THE YES all along. I understand now that my passion is leading organizations and leading people… dreaming up new ideas and then making them a reality... and building great shopping experiences.

?When I was leaving Stitch Fix and deciding what to do next, there were a couple CEO retail jobs I was exploring, but I recognized that the company that I was confident would succeed in the future, was a company that I designed and built for the future. Because it was my own idea, I would feel really comfortable running it. I wasn’t going into another organization and structure and run aspects of a business that I didn’t know about. THE YES was my own creation, and that was wonderful! And as I thought about the future of THE YES, I assumed we would be acquired at some point, knowing how expensive it is to invest in technology - and we were a technology platform, not a retailer. I knew if we were to stay on the cutting edge of technology it would probably be a tech company that would buy us – a tech company that wanted to get into shopping. When I was launching THE YES, so many people were asking me if I was worried about Instagram, Google, and Facebook. I always believed that none of these companies had shopping in their DNA. They may evolve to a place of impulse buying but they’re never going to become destinations for shopping – that’s not who they are or the direction they were developing their business.?Then there is Pinterest. People already wanted to shop on their platform, and they wanted to learn what it would take to make it shoppable. Pinterest was on my dream list for down the road, but it happened sooner than I had thought - and here we are.

My outside interests and board activity have always helped to keep me educated and connected with the goings-on outside of my narrow world of fashion e-commerce. It is important to get inspiration from other industries and other viewpoints. Leadership-wise, being on boards is valuable and contributes to the company roles one plays… you understand more clearly what boards are looking for; it has made me a better leader and CEO. My outside interests have kept me sane. I’ve had two children grow up and one go off to college. All of this makes you a more humane leader and keeps things in perspective. Younger women who are torn about whether to have children have asked me about the impact being a mom may have on their career. I have experienced and have witnessed that if you are a committed, dedicated person, that’s who you are to both your job and your kids … they all feel it, and it forces you to focus on the things that matter most.

TBB:?Given you are a Harvard graduate with both a Bachelor of Arts degree in government and an MBA, this is impressive and highlights early academic success and strong aspirations for the future. How would you describe that time in your life and what personal characteristics drove you to Harvard? How did that experience shape your career path?

JB:?It all stems from what happens in your home. I was the middle child of three girls, and I was the “dumb one” (with the perspective that both of my sisters were super-academic). I was also interested in fashion, to add to the viewpoint. By the time I got to high school, I decided I was going to show them they were wrong. A small chip on my shoulder developed, but a big enough one that I wanted to prove myself to my family. My sisters felt it was expected that they go into hard core academia along with some pressure. I felt a little bit more freedom from a career perspective. They both went onto law school - one of them is now a professor and one is a lawyer in the non-profit sector. I was never interested in law, but also being a lawyer is the opposite of my personality; I like to break the rules. Overall, I experienced more freedom to forge my own path both in education and throughout my career. However, in the business world, Harvard undergrad has been fairly insignificant for advancing in my career. But Harvard Business School has been wildly beneficial. All of the people from HBS remained in my orbit and led to making connections. Many have played some sort of a role in my career throughout the years.

When I graduated from Harvard and decided to work in fashion, I remember Mary Wong, the SVP at Donna Karan, where I got my first job, saying to me, “I don’t care that you went to Harvard, you’re starting at the bottom here.” That was so fine with me … but it almost felt like it was a point against me. That was my career start, and as I continued to find my way I experimented with a bunch of different jobs. After working at Donna Karan, I thought I should do something with some social impact, so I worked at a foundation for some time, but found it was too slow-paced for me. It was time for a reset by now, so I went back to business school, worked in finance and investment banking with the intention of developing some hard skills, and eventually found my way back to retail. I enjoyed the business side of retail – so dynamic and interesting. This is when I joined Starbucks briefly before learning Nordstrom was launching e-commerce. That was attractive - I spent six months trying to get them to hire me.?Sometimes the path to your dreams isn’t straight - it was a winding road to get to my sweet spot of e-commerce, and it was worth the trip. I often tell younger people that the process of elimination is as valuable as finding the perfect thing.

TBB:?Early in your career, while you were with Donna Karan Company, you were quickly on an intentional course by initiating projects and introducing forecasting tools. This was long before the technology and information age was prominent where consumer data, tracking and A1 was a part of every business. Tell us about being one of the first to truly embrace digital and knowing then it was such a vital part of the evolving retail industry.

JB:?I’ve always been slightly obsessed with efficiency. My husband, who I met in business school, used to tease me about this trait. It’s the lens I view life through. When I got to Donna Karan, intuitively, what we were doing didn’t make sense to me. A history of Donna Karan orders existed, and we had no access to them. We were just writing new orders by hand - my boss was using a pencil on graph paper every day. At the time, IT was referred to as MIS and the girl in charge of this was the go-to girl. She knew her stuff. We all had computers on our desks, but we weren’t using them. I asked the MIS/IT girl if she would help me. There was a basic tool I wanted to build but couldn’t do it alone. This is an example of how I’m naturally wired. I like solving problems systematically and coming up with novel ways to fix them. Technology to me is a tool. While I’m not a coder, I understand the concept of how you build technology, which allows me to work well with engineers. I imagine it goes back to my upbringing. My dad was a doctor and used a computer since the early 80’s - this had quite an influence on me. Technology is a source of great information to systemize, optimize, and speed things up.

My first practical use of AI was with Stitch Fix. As I learned about the models they were building, I understood how to take the logic in my head and create formulas - with the machine calculating a computation that began in my head. I have always been drawn to technology and its ability to solve problems and working closely with engineers to build e-commerce. Prior to my time with Sephora, the world was just getting the basics up and running with technology in retail. When I joined Sephora, the world really began to change and that was super fun and interesting. At Stitch Fix, I worked closely with the data science team and that opened my eyes to machine learning and AI in the form of matching people and products in a very meaningful way.

We launched Beauty Insider which took Sephora to a new level of retail as they became best known in the industry for digital savvy and consumer loyalty. We created a beauty community with conversation online and were the first to launch a mobile app and mobile website that would enhance the in-store experience for the consumer. You could scan products in-store and keep track of all your past purchases. Loyalty points were all tracked and maintained on your phone. It was the prime of allowing digital to drive the business forward. This innovation had a huge impact on us, doubling the retail business and growing the online business eight times over. Our CEO, David Suliteanu, was wonderful to work with and a champion of mine. The company was set up in a way that was uncomplicated and easy to get things done. We were lean, without tons of layers, and able to make things happen efficiently. I enjoyed a wonderful eight years at Sephora.

We all have innate abilities – mine is to creatively visualize things in my head and communicate well with coders and engineers; it comes naturally. I am a huge fan of the whiteboard with drawings playing a big part in my vision. My focus has always been simple - how do we use technology to make the consumer experience better by solving problems. During that era when technology was taking root in retail space, others created a lot of bells and whistles, like videos in stores and mirrors that would talk to you. None of that stuff ever really stuck, although it got press. At Sephora, we focused on making sure we were solving practical problems - like when you are out of town and run out of foundation, how do you know what color you usually buy. Or if someone has a question, who can they ask and get real-time answers. We had a great CTO, our tech partner, Savio Thattil, who is now with Capital One.?Because we didn’t have all the skills in-house to develop some of these technologies, we found it outside. I remember wanting to do mobile in 2009, and at the time mobile developers had not yet been trained. So, we hired a group of kids who had just graduated from Carnegie Mellon, and they built an app and website specifically for us that was really effective. They went on to build one of the most successful mobile app firms called Branding Brand, building hundreds of other retail apps. Working with them and collaborating with them was pivotal for Sephora.

Also, with the release of Apple Pay, I signed us up.?The second it came out I was thinking, “Finally, why do I need my credit card if I have my phone; phones are so intelligent.” We rolled out Apple Pay across all of our stores almost immediately. I was such an advocate for it in our company. I felt unique in my role – there weren’t a lot of people in senior positions who were embracing technology and making things happen. I was a rising leader during a real transitional time in technology and positioned perfectly to initiate meaningful change that enriched the consumer experience. With both Nordstrom and Sephora, I was in a senior position and reporting directly to the CEO, giving me the leverage to actually influence and drive decisions. The CEOs believed in me and trusted me, which was inspiring. Most of the leaders in retail at this time were not of my generation - they were from one generation before. I had the advantage of being of the age that grew up with and embraced technology as e-commerce emerged in the industry.

TBB:?Your career pivots led you to a few positions in the investment banking world, with client experiences that kept you engaged in the trends of retail and food and beverage brands. What skills and insights did you gather during that time and how did it impact your next steps and the role you played in retail organizations such as Starbucks, Nordstrom, Urban Outfitters, Sephora, Stitch Fix, THE YES, and now Pinterest?

JB:?I wanted to understand what went on in the world of finance and investment banking at Robertson Stephens. I felt a little intimidated by it and I didn’t like that feeling. So, I embraced it with a goal of a deeper understanding, to see if I liked it, and simply to make sure I wasn’t missing anything. My career path took on an education role at that time, which allowed me to understand how companies finance, what “going public” and selling a company entails, and how you evaluate and analyze the fundamentals and financials. For me, it was a year and a half of excellent training. It afforded me a practical and viable comprehension of the role of finance and the layers of business that it impacts. I also learned that this was not the direction I wanted in my career - the other side of the table was so much more interesting for me. The investment of time though has proven to be critical and beneficial in understanding the finance side of the world. Soon after that, I joined Starbucks for business development and M&A, and while I was a member of the team, we acquired Hear Music in 1999. I went so much deeper in understanding the P&Ls of a company by being on the inside and actually grasping what would happen during the acquisition. That stage deepened my knowledge base and the contribution I could share in my role. It also became relevant when I was selling my own company, THE YES. My team and I had such a depth of know-how about how deals get done that we served as our own investment bankers, without the need to hire a firm. I would definitely say that my financial career pivot provided a broadening of my business acumen for all my future career roles.

TBB:?Accomplishments tell a story, and yours begins with an early awareness of the value of metrics and the power of information to drive decisions, strategies, efficiencies, investments, and profits. You use technology to help solve problems and promote growth, weaving together marketing and digital innovation.?We’ve learned that you have always seen marketing as two-way, standardizing some of the metrics, and using information to create smart growth. How did that early understanding position you for the path you are on?

JB:?I think I am naturally a right brain, left brain person, always enjoying both math along with art and design. I’m not one more than the other. My roles have given me the opportunity to be involved in the creative parts, but also incorporate analytical thinking. The general management of e-commerce allows me to merge together those two sides of my brain and the different facets of business.

Also, I trust my gut a lot. Because I’m the consumer myself - I’m not trying to understand what others might want. I’ve always thought it was an advantage - being the consumer of your own business. You just intuitively understand what is needed to make a better shopping experience. And the data is so powerful in measuring results and validating information. Technology continues to evolve as an effective tool in scaling and automating the process. As my career has played out and I look back, I realize that you don’t have to be one or the other, creative or analytical … you can be both. I’ve loved that aspect of combining both my systematic knowledge and artistic passions to drive innovation.

TBB:?The “experience” for a shopper over the past two decades has transformed to what might be categorized as a form of “entertainment.” What was once in-person within brick and mortar is now a hybrid that includes a growing e-commerce continuing to move in the digital-forward direction. Shopping is now combined with creativity and discovery from consumers … it’s experiential, inspiring, and fresh … and it caters to individual uniqueness rather than broad categories. Share with us a “window into the future” of what a shopper experience will become?

JB:?The first 20 years of e-commerce were really about getting stores online – getting the product photographed, writing up descriptions, and figuring out how to execute the sale online to take the money. The burden of finding what is right for you has been on the consumer - they need to understand the words we use, the category trees we create, and find what they’re looking for. As e-commerce travels through the next ten years, it is going to be more about how technology gives shopping online an advantage. There are a couple of aspects of that that I envision - one is the ability to use artificial intelligence to understand consumer preferences and serve up suggestions that hit the mark, customized for each consumer. As the world has shifted dramatically online, this can be totally overwhelming, creating a noisy environment to shop within. It’s difficult to find the stuff that is right for you, in terms of both content and product. Finding what is right and relevant for each consumer is our problem to solve, not the consumer’s.

I see this as a combination of AI and Social - AI providing information to understand preferences and serve up the right offerings, and Social being the community you care about – the tastemakers, delivering the relevance with people, interests, and suggestions that are meaningful to you. AI allows us to build an understanding of the consumer and an understanding of the product category, and then build algorithms to make personalized recommendations. Technology can transform the sea of products that you now have to fish through to an assortment that is a match for each individual consumer…whether coming to look for something specific or being provided suggestions and sent directly to you. Even the nuances of why you like something and what is served to you is just going to improve continuously over time. Our ability to deeply understand product and consumers is there… it’s up to us to expand on it.

Trust also remains key in this online world. It’s everything. If you don’t have it, nothing else matters. At THE YES, we were conversational and interactive, making it very clear to the consumer that our detailed “ask” was in order to make the experience better for them. Trust needs to be in every element of the business, as it always has. At THE YES, we had no rules around “doing right by our customers.” We just needed to do it and do it right. If we messed up, we would take care of it. It’s a simple formula.

Pinterest is one of the last safe havens in social media. It focuses on the life you want to build.?It’s all about getting inspired – dreaming, imagining, and planning. This company takes seriously anything that is negative. Technology can create a lot of unintended and unforeseen consequences. You try, but you can’t always predict what is going to happen. But you can take a stance on it, and you can control it - if you choose to. At Pinterest, the team really cares about building a trusted and safe consumer experience and shopping environment.

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