I’m not a designer. Neither is my company’s cofounder, Charlie Kroll, but when he suggested hiring a chief design officer for Ellevest, the digital investment platform for women that we launched this year, I listened.
I’d spent a career in the corporate world before turning entrepreneur, whereas Charlie has a startup background. I had always thought of good design as making things look nice, but have learned it’s much more than that—especially if you’re starting a business that aims to change individuals’ behaviors, not just capitalize on their existing ones. (And ours does.)
Charlie’s instincts have since proved right. What’s more, I’ve learned how crucial it is to bring a design head into your startup as early as possible. Here’s why.
The challenge we’ve set for ourselves at Ellevest is simple: to get women to invest more. Achieving it is difficult. It involves real behavioral change in our potential users; this isn’t comfortable stuff for them, or they’d already be doing it. Most of the large investing firms—with a lot more money and resources than we have—have tried to solve this issue and failed.
So I understood from the beginning that we couldn’t innovate along just one dimension, like through changes to our investing product or by reaching women online instead of in person. Instead, we’d need to open up multiple avenues for building our user base all at once. And design had to be one of them.
Ellevest’s chief design officer is Melissa Cullens. She helped redesign Vogue.com and Sirius radio, and she was part of the team behind the great James Beard Award finalist PieLab, a bakery with a social mission. Melissa quickly helped me understand that good design can be the difference between a good product and a great product—between a user’s intention ("I’ll get to it later") and action ("I’ve got to do this right away"), and a company’s success and failure.
But as any designer can tell you, design is a lot of hard work, with few shortcuts. It starts with getting to know your subject well—really well, not just "we conducted a survey" well. The way we’ve worked design into our process involved hundreds of hours of product testing with women, starting before we even wrote a single line of code.
To understand women’s relationships with money, it wasn’t just asking them questions, but having them bring in financial statements and walking through them together. It was spending time with women to work through how they manage their money, in practical terms.
And only then was it asking women to check out our initial designs on Usertesting.com and in our offices—followed by me sending personal emails to everyone who has been invited to become a client, asking for their feedback (and receiving paragraphs and paragraphs in response). These may not sound like design challenges, but they are; all this grunt work was essential for us to understand what the hell it was that our users needed designed in the first place.
Even after all that, there were still countless back-to-the-drawing-board moments. But that’s simply what the design process involves if you’re using it to understand your users better, not just make an already-built product look flashy—when you’re using it from the very outset to solve the problems that will make or break your startup.
That’s why it’s so crucial to involve a designer in the earliest stages of conceptualizing. It means you’ll be designing for the problem at hand—not the one you believe exists. And trust me, there’s a difference.
In my case, I thought women would embrace investing after we helped them go on "an emotional journey" that addressed their feelings about money (think: Cosmo quiz to find your perfect boyfriend, just about investing . . . I know, it sounded a lot better in my head than when I see it on my computer screen). But after all, I’d spent my career on Wall Street, where I had a front-row seat to "women’s investing initiatives" that involved discussions (led by men) of how women were "too scared" to invest or "too risk-averse" to invest. I pretty much took it as fact, because, well, women really don’t invest as much.
I shared this hypothesis with the team, and Melissa got to work, spending time with women in our target market to understand what tools they use in other aspects of their lives, how they access their retirement accounts, how they think about money—you name it. She mapped out behavioral patterns and determined from our research that women are practical and want a practical investing solution, not an emotional experience. But even after that, since I was the boss and had a strongly held hypothesis, she then designed the emotional journey I’d asked for.
And it fell flat—worse, actually: Women pretty much gave us the finger. Which wasn’t at all surprising given the research Melissa collected to design her iteration of the site. This taught me something that we non-designers often overlook: Design is as much a method of sifting out a business problem as it is a method of execution.
Melissa’s design research was crucial to the business model—not just determining a font and color palette. And by including her in the product process early on, rather than bringing her in at the last minute to realize a vision she had no connection to, we were able to adjust before it was too late.
As an entrepreneur, it’s easy to feel ownership over every aspect of your business because you’re putting your reputation, your money, and other people’s money on the line. Oh, and you’re sleeping, breathing, and eating your passion project—that, too. But if you try to do it all yourself, you’re almost certain to fail. I had to remind myself that you hire people because of the skills and ideas they bring to the table, which means giving them the space to work through problems on their own.
This meant we got caught in some ratholes. There was the idea we had of displaying a user’s money today and tomorrow’s projected money as a string of concentric circles. It doesn’t make much sense when you read it; and, believe me, it didn’t when you saw it, either. But we spent weeks trying to make it work. Then there was the concept of projecting out our client’s probability of reaching her goals into the future through some sort of visual element. Yeah, that didn’t work either.
And then there were the ideas that hit the bull's-eye—those that came straight from the design research but still took Melissa some time to bring to life. These included an easy onboarding process, in which the client fills in a Mad-Libs–style questionnaire (in real human language, unlike the dense questionnaires so many investing firms use). There was the design to show our clients the reasonable worst cases for their investment portfolio performance, to address their questions of how much money they might lose in a tough market. (No, women are not too "risk averse" to invest; our research shows they simply want to understand risk better than existing services allow them to.)
Finally, there was the overall design sensibility that was more similar to Vogue.com than to MyMerrill.com. Our users told us that existing offerings were off-putting. They wanted a site that respected (and celebrated) the commitment they were making in investing—one that focused on their real-life goals, as opposed to investing jargon. That took a while to nail, too, but was worth fine tuning.
Taking a step back as CEO isn’t the same as checking out, but there’s no point in being involved with every step of the design process if you aren’t a designer. Instead, we created a culture of communication with regular check-ins, where the senior team could weigh in periodically on the design process without getting in the way.
A closing insight: Everyone seems to think they have a great design idea. As a startup founder, no doubt you do, too. This may be the best argument in favor of hiring a design head from the very outset: It simply lessens your risk of self-sabotage over your own misguided and inexpert design ideas. Instead, it’s your job as a founder to make sure your senior team members have room to do their own jobs—which means not every design idea is going to be tested or adopted, including your own.