Whitney Casey Is Creating Empathic Technology & Rocking It

Thanks to the influence of pop culture, most of us ‘90s kids grew up with the fantasy of a digital wardrobe. You know what I’m talking about — a revolving, computerized closet full of plaid miniskirts, fuzzy sweaters, and dreams. For those of you who thought that childhood fantasy would always remain just that, you should know about Whitney Casey and her company Finery.

On behalf of MicrosoftMicrosoft Surface Laptop, she and I are talking today about women in tech and how she got her start, as part of our "Run With Me" series. In this series, we're bringing you stories of remarkable women in tech, and discussing how they run their lives and run the world.

"Finery is the world’s first operating system for your wardrobe," Whitney tells me. Talking enthusiastically with her hands, she continues: "The technology finds the past 10 years of purchases, everything you’ve ever purchased online, and we populate an online closet!"

When you talk to Casey, you get a sense that she could make anyone excited about anything. She has a huge smile and an effusive demeanor. Originally from Danville, she looks and seems every part of the California girl she is — tall, blonde, warm. But don’t let the Pacific Coast chillness fool you; Casey is the kind of ambitious powerhouse who's not only had one high-profile career, but several.

In addition to talking us about her life, Casey is also sharing some selects from her own closet, including a gorgeous studded leather jacket, a sleek silken jumpsuit, and numerous pairs of chunky loafer heels. My co-workers and I were gagging in the best way.

“Even if you aren’t a fashionista, you will spend 2.5 years of your life picking out what to wear, and eight years of your life shopping. And that’s just too much. Even if you enjoy it.” In Casey’s words, we can't afford to waste the time, money, and brainpower we expend while getting dressed.

When developing the product, Casey thought of what she’d like to have in a closet inventory system — things like return countdowns, sale notifications, and a visual index of styling references. And with Finery’s growing user base, the idea is catching on.

Before Casey was pitching her company to massive venture capital firms, she was behind the newsdesk. After getting a pre-med degree from the University of Virginia, Casey went to work for Fox News, and later for CNN. Her decades-long career in news saw her interviewing world leaders, former presidents, and A-List actors, earning her two Emmy Awards.

The former journalist’s introduction to tech was a bit of a serendipitous one, if not perfect kismet. Casey began writing a relationship column for, becoming their foremost relationship expert. As she tells me, the CEO at the time saw her curiosity and willingness to get in the trenches, so she brought her into the product development meetings. Just like in her column, she was boots on the ground, interviewing men and women about product design, what they wanted from a dating experience, and what they didn’t. She was able to shape the point of view of the service and really see how people reacted to it.

“That got me really good at making a product with empathy for users,” she tells me, “and I think that’s what good design is. Problem solving in general and problem solving in technology is having empathy, and as a news person if you don’t have empathy you don’t have a good interview.”

When her product was finally developed and ready to pitch, she had the edge of being able to relate to her user. Her user, however, was not always the demographic she was pitching to in board rooms. The Finery’s key demographic is overwhelmingly female, and as it goes without saying, the upper echelons of the tech world is not.

“I am experiencing a limit every day being a woman in technology, because there’s only six percent of us,” she tells me with an incredulous laugh. “I’ll let you know when I’ve overcome it. I’ll let you know when we reach critical mass.” However, using her savvy and ability to get out of her own perspective, she’s wheeled, dealed, and learned how to sell her product in terms that the testosterone-fueled VC world can understand, as she tells me. In essence, she sells her product the way a man would. The title of her hypothetical memoir— "No Is Just A Conversation Starter," she tells me — speaks to the tenacity that any person, particularly a woman, needs to have in the start-up landscape.

Though the start-up world needs more female CEOs, Casey sees a move in the right direction toward gender equality in tech. “Female-owned companies are metastasizing,” she says, nodding her head resolutely. “This is a space that women are helping each other… There is a movement, and the movement is starting in tech, and that’s what’s so cool.”

And while the movement is building, there’s no time to rest on one’s laurels. Hustling is more important than ever, and like all CEOs, Casey has her tips and tricks to remaining on-the-go. In addition to her wardrobe operating system, she swears by her Surface PenMicrosoft Surface. As she tells me, it cuts her time editing the interface of her website down exponentially. “My team knows I’m obsessed with it,” she laughs. “I call it ‘penning.’ People will be looking for me, and then they’ll say, ‘Oh, Whitney’s just busy penning.”

Between her career in media, her career in tech, and her own lust-worthy closet, I wonder what her childhood self would say if she met the Whitney of today. “I think she’d just be disappointed she wasn’t president of the United States.” Hey! It isn’t too late.

This article is brought to you with the help of Microsoft Surface.

Curious about the laptop Whitney is holding? The brand-new Surface LaptopMicrosoft Surface Laptop was released this June, featuring the following:

  • Ultra-thin and light, so it fits easily in your bag.
  • Four tone-on-tone color combinations and sleek, elegant design complement your personal style.
  • Enjoy a natural typing and trackpad experience, enhanced by a luxurious Alcantara® fabric-covered keyboard.
  • The power to do what you want with all-day battery life.
  • Experience beautiful images in true-to-life color on the vibrant 13.5” PixelSense™ Display with touchscreen.
  • Invisible immersive Dolby® Audio™ Premium sound that comes directly from the keyboard, with no added bulk or grills.

Images: Joshua Pestka; Art Direction: Jenna Wexler/Bustle; Design: Mary Blount/Bustle; Hair: Marcos Diaz; Makeup: Katie Jane Hughes; Wardrobe: Whitney's own.