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Eighteen months ago I started working as a designer at Oracle. Here’s what happened.

By Hillel Cooperman, senior vice president, user experience design, Oracle—Sep 16, 2019


Hillel Cooperman

In late 2017 I got a call from a senior leader at Oracle. They asked me if I was interested in coming to be a designer there. I’m embarrassed to say that despite being in the high-tech industry for multiple decades, I didn’t really know what Oracle might need help designing. I imagined there was some user interface for configuring databases, but I didn’t know what else. I learned quickly that Oracle had a comprehensive suite of cloud applications for running large businesses and those apps had lots of users and an enormous amount of user interface. And while Oracle had talented and thoughtful designers, they were looking for help to elevate their user experience to a new level.

To be quite honest, I was skeptical. 

I didn’t know what to make of Oracle. I didn’t know what to make of enterprise software. And I didn’t know what to make of their professed commitment to elevating their user experience. I asked questions. Lots of questions. What kind of latitude would I have? What kind of resources would there be? What kind of support would there be? Ultimately, I believe that designers don’t create the user experience, but company cultures create user experience. And if you want a great one, every single person at the company has to be on board. And making that happen isn’t just doing user experience design, it’s changing company culture. I’ve done enough upstream swimming in my career to know that changing culture in a place that’s not receptive is a difficult proposition at best. The folks at Oracle said they were serious about all of this.

On the off chance that this could possibly be true, I took the job.

The first thing that struck me about Oracle was the people I met. Collaborative, authentic, introspective, and eager to grow and improve are the first impressions that come to mind. I know there are people like that at every company. But I was surprised at how consistently I found these qualities in the people I had come to work with. They were patient with me. And they needed to be, because despite the commitments to change from senior leadership, I was still skeptical. I’ve been lucky to have some fabulous opportunities in my career, but the opportunity to really redesign the experience for a tech icon from the bottom up seemed too good to be true. And maybe, a small part of me, thought it couldn’t be true, because if it were, why would they have hired me?

And in the first weeks and months of my job, I realized that they were actually serious. You would think that my first reaction to the realization that this really was the job I had dreamed of would be excitement. And it was, for about a minute. But the next reaction, the stronger one, was fear. 

First some context. I didn’t start out as a designer. I started out as a product manager (or as it was called where I was, a program manager). I learned early in my career that designers were the magical ingredient for turning good products into great ones. And I was lucky to work with some pretty incredible designers that welcomed me into their world. I was even lucky enough to co-lead a creative agency for almost ten years with the best designer I’ve ever worked with – Jenny Lam. And since we were very small, there was no choice, I had to draw too. And I drew a lot. I think it was somewhere in year seven that Jenny finally came to me one day and said “I think you can call yourself a designer now.” I was floored. But after seven years of her patient mentorship and coaching, I had earned her trust as a designer in my own right. That was a really good day. 

But now, the job I had wanted, to help design an entire company’s experience, was mine, and I wondered if I was really up to the task. It was easy to want it when it seemed like there was no hope of ever getting it. Be careful what you wish for. After a bit of anxiety and stress, the answer finally came to me. If I could convince all my friends who were way better designers than me to come work at Oracle, and they could convince their friends, and we could rally with the great designers and researchers and engineers and product managers Oracle already had, we might be able to pull it off. Needless to say, I called the best one I knew – Jenny.

The job I had prior to coming to Oracle gave me several gifts. One was the gift of a growth mindset. Or at least the aspiration to have one. And because of that, I genuinely believe there is almost always more than one good way to get something done. More than one valid approach. And more than one successful outcome possible. That said, I believe that there are three important principles that companies, which I love all share. Companies like IKEA, or Disney, or Apple, or Starbucks. 

1. They believe that every single interaction with a customer (or the public, or a partner, or an employee) contributes to the overall user experience. The user experience isn’t just the user interface. It’s the product and the marketing. It’s customer support and sales. It’s digital and physical.

2. They believe that every one of those interactions is an opportunity to tell a unique and differentiated story. Not a list of features and functions of their product, but a story about why they come to work every day. A story about why their company exists.

3. They believe that telling that story effectively and beautifully is every single employee’s job regardless of their role or function. Those companies are design led, not designer led.

That is the user experience that I have always wanted to be a part of crafting. That is the experience that I’ve always wanted to have at work. And, that is what Jenny and dozens of our industry friends banded together with many Oracle veterans to do.

My boss manages one of Silicon Valley’s most innovative and sizable teams and is responsible for multiple applications’ product lines at Oracle. He’s got a significant amount of responsibility. But, when he’s asked about his role, he says he “takes care” of those businesses at Oracle. I think Jenny and I were both inspired by that. Jenny and I, and the great leaders we work with were tasked with taking care of the Oracle user experience. And for the last eighteen months, that’s what we’ve been giving our all to do. 

Nominally, the team I’m on has been working on the design of our products, and Jenny’s team has been working on the design of our brand and marketing experience. But mine and Jenny’s long creative partnership and Oracle’s trust has afforded us the opportunity to blur those lines. Jenny and I have been fortunate to work with our teams and the other design teams at Oracle as one large group that we call (naturally) Oracle Design. No separate team names. No territorial debates. Just one large group of people eager to improve the lives of our end users. And the first thing we looked to do was to create a brand new, modern, user experience design system that scaled. Massively.

For eighteen months, the amazing multi-disciplinary folks at Oracle Design as well as all our partners in product development, marketing, sales, senior leadership, and more have been working to create a brand new state-of-the-art design system that works for periodic users, and power users. That works for end users and developers. That works for content-heavy experiences and works for interaction-focused experiences. That works for digital experiences, and physical ones like our annual Oracle OpenWorld conference. Anyone who works in design knows how often there can be arguments about how one design system couldn’t possibly scale to all those needs. But those arguments didn’t happen at Oracle. Instead, with some pretty great support from senior leadership, all these groups came together to create a system that’s flexible, that’s expressive, that scales, that tells our unique story, and that’s constantly evolving based on design research, learning, and listening. And while we are still at the beginning of our journey, and have a lot of important and intensive work ahead of us to bring this user experience to our customers at scale, I could not be more thrilled to share with you a sneak preview of what Jenny and I and several thousand of our best work friends have been up to. 

It’s called Redwood. Take a look for yourself.


This is just the very beginning. There are daily constants to our work: understanding the nuances of the challenges our customers are dealing with, elevating our own efforts to help our customers meet those challenges in ways they hadn’t imagined, and learning and improving every single day. While we’re working to get our users to fall in love with Oracle one interaction at a time, we want them to fall in love because when they use our products each day, ultimately, they feel understood.

In retrospect, there was no need for me to be scared. Solving the hardest problems, (Oracle’s forte) is almost always a team sport. I never thought that Oracle would be the place where I was lucky enough to be surrounded by so many people I can learn from on a daily basis. And where I could be a small part of such a committed and sweeping effort to elevate the experience working with one of tech’s iconic brands. But that’s what happened and that’s what continues to happen every single day. Our journey continues, and I hope you’ll stay tuned to see where we go from here.