Tenacious Women and the Art of the Drive-By

An Interview with GUILD Member Jessica Davies

Jessica Davies is a strategist, UX researcher, UX Designer, developer … and skydiver. She holds a Master of Public Health from Harvard University, and an undergraduate degree in Psychology from UC Berkeley. Her sleek and creative website offers a traditional and “cool” version of her resume. Both are impressive. She was a Wall Street analyst and portfolio manager, has worked on four startups and brought two products to market. She never stops learning and is a true unicorn, transitioning to become a designer and web developer in her 40s. In short, Jessica Davies is an accomplished professional with some serious credentials. This week, we talked to her about her remarkable career and her recent experiences beta-testing the GUILD.

Interview by Susanna Camp.

What woman/women do you admire?

My grandmother was a stockbroker in the 1960s, when women weren’t even supposed to have jobs outside of the secretarial pool. She worked until she was 92 and still manages her own portfolio. My mother was a file clerk in the 70s, then went back to school and became a teacher at 40. These were my early role models.

At this moment, I would have to say the woman I most admire is Hillary Clinton. She put up with so much crap. She had to debate a monkey (which is an insult to monkeys). She is a woman who actually won, but technically lost. And she was a classy, professional, kick-ass broad the whole time.

How did you decide what to study in college and how did that lead (directly or indirectly) to your career?

At the time my father told me psychology was a useless, stupid degree. But psychology is one of the three degrees — along with anthropology and design — that actually is sought after in UX Design. So it’s ironic. The degree that was supposed to be useless actually ties directly to my fourth career as a UX designer and researcher.

Were there any unexpected influences that determined your choice of career?

I went to Wall Street pre-bubble, in 1999. I didn’t have a Wall Street background or an MBA. I just had some friends that encouraged me to get into it. I moved to New York not for a specific job, but just because I wanted to live there. And I had a terrible job at the time. I would cry all the way to work and again on my way home. But moving to NY led to my research analyst job on The Street, which led to strategy, and then I pivoted again to UX, which is where I am now.

What’s the funniest job you’ve ever had?

My first job, I was in high school. I got paid fifty cents higher than minimum wage, so I made $3.75 an hour. I worked as a hostess at Bobby McGee’s, a theme restaurant. And I had to dress up as Snow White. Humiliating now, but I loved it at the time. And I got a great picture out of it.

How does your personal passion take you further in your profession?

I have an innate ability to see things that are wrong and a keen attention to detail. Here’s an example: my mom and I went out to a restaurant and we were given three menus apiece. It was confusing! So I asked for the manager. He said, “Some people want to order off the dinner menu.” Well then, give them the dinner menu. Don’t give everyone three menus! I notice these things and not everyone does. (My mother, for one.) It’s important to notice things, because this is what makes the customer have a bad experience. They might not even be conscious of why; they just know it sucks. One of my professors said, “The devil is in the details.” And not everyone sees these details. So sometimes I have to see for them. UX experience is also about helping people understand and navigate the experience and being their advocate. What I really want as a designer is to make sure they have a good experience, even if they don’t know why.

What advice would you give to your 20-year-old self?

Quit sooner. This means relationships, jobs, or friendships — anything that is not working. I would quit it sooner and move on. And move on more fully. I would move on and stop thinking about it. What really holds people back is when they keep doing something that’s not working. Or, even if you’re not still doing it, you’re still thinking about it! They always tell you not to be a quitter, so it seems counterintuitive. But what I would say to my 20-year-old self is: Quit early, often, and more fully!

What is your favorite networking method and why?

I call this the Drive-By. I’m pretty tenacious, so if I meet somebody or hear somebody speak, even if I haven’t met them, but just have some sort of tie with them, I will track them down like a dog. I have an example. I went to Pinterest a couple of years ago and saw a presentation. I liked the head of research even though I never really met him. I LinkedIn with him, then proceeded to bug him monthly until he gave me a meeting. Then I had several meetings with him and learned that he had connections at IDEO, where I’ve always wanted to work. It took several months until he got to know me, but he connected me to a friend of his at IDEO, and now — I’m working for IDEO on contract until the end of next year.

So, this is the Drive-By: see someone who could be helpful to you at some point, five minutes from now, or five years from now. And track them down until you get to meet them. Wash, rinse, repeat — until you get what you want.

Why did you join the GUILD? What did you learn from beta-testing and what do you want to get out of it?

I quickly became underwhelmed by the networking opportunities in San Francisco. The worst were the founder meet-ups. There was a lot of negativity, jockeying for position, and men bringing a lot of bravado. They talk about launching their startup in a garage. But you are pretty sure it’s their mom’s garage. And then they drop some vague comment about $100 million. Did they sell their company for $100 million? If so, why are they not chillin’ on a beach somewhere? There are a lot of young and insecure men in these networking groups. And then there are the other kind of meet-ups, sponsor meet-ups. There is no real time to network, just a sponsored talk and then everyone gets up and leaves.

Then I joined some women-only groups: The Expat Woman, Women Who Tech, Women Who Code, and the GUILD — and I had much more positive experiences. Amazing people, open, trying to learn from each other, not trying to prove something. And I realized it was not worth it to be a part of co-ed networking groups.

As part of the GUILD beta-testing, I was matched with three women. And even those who weren’t in my industry turned out to be amazing. I really believe one-on-one networking is most effective.

What’s your mantra?

“Kick ass and take names.”
Jessica Davies, far left, at the GUILD Launch event in November 2016.