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BigLaw to Entrepreneur: Career Inspiration and Style Tips from StyleBee CEO Anna Santeramo

W hat do you get when you mix the dedicated productivity of New York BigLaw with the risk-taking hustle of Silicon Valley entrepreneurship? Add a dash of style, and you’ve got Anna Santeramo, co-founder and CEO of STYLEBEE: an app that lets busy professional women (and men!) book on-demand, in-home beauty services like haircuts and blowouts by using their smartphones

Santeramo loves being productive — after all, that’s how you thrive at a big New York law firm. In fact, although StyleBee may seem like a regular beauty app, it was created to make beauty affordable and convenient for everyone. “When professional women shop, they want to be as productive as possible,” Santeramo declares. “Who has the time to be lost in a department store? Who has the time to aimlessly click through pages of online shopping options? And, of course, who has the time to plan ahead, book in advance, travel, and sit for a professional styling?”

Anna SanteramoSanteramo notices that most lifestyle routines are being simplified and optimized for busy professional women. “The trend that’s happening in the past few years is that companies want to make it easier for professional women to do everything, from shopping to dating,” she says. “Why spend time on these things when professional women have less time than ever? They want to spend the few free hours they have with their friends and family or relaxing. Taking care of beauty routines is usually not an idea of a good time for most women, especially professional women.” But when it comes to beauty services, Santeramo explains, professional women often settle for lower quality and less convenience because they are not aware of high-quality, convenient style options.

One day it occurred to Santeramo that she could democratize beauty services and make them both affordable and accessible. So she headed west to make her dream a reality.  

To say that Santeramo fits into Silicon Valley culture is an understatement. She quit her distinguished, stable, high-paying law firm job. She traded her suit for the ubiquitous entrepreneur hoodie and learned enough about coding and tech to become Silicon Valley-fluent. She then joined Y Combinator, a prestigious, very competitive rite of passage for numerous Silicon Valley startups.

What inspired Santeramo to make such a bold move? Santeramo proudly quotes the late Silicon Valley legend Steve Jobs: “When you grow up, you tend to get told that the world is the way it is and your life is just to live your life inside the world, try not to bash into the walls too much, try to have a nice family, have fun, save a little money. That’s a very limited life.” Jobs’ quote, which Santeramo is inspired by even years after her move, continues: “Life can be much broader once you discover one simple fact, and that is that everything around you that you call life was made up by people that were no smarter than you. And you can change it, you can influence it, you can build your own things that other people can use. Once you learn that, you’ll never be the same again.”

Santeramo has taken this quote to heart throughout her journey from BigLaw attorney to startup CEO. Instead of letting her dream pass her by as she worked a conventional job, she took a risk and set out to change her life. And Silicon Valley rewarded her risk-taking. As of July 2015, StyleBee had raised US$1 million in venture capital from both Y Combinator and other high-profile Silicon Valley investors, and recruited 600 professional stylists for its on-demand services.  

With StyleBee’s success on the rise, Santeramo has a busy schedule riding the Silicon Valley roller coaster. However, she still makes time for her personal beauty routine and enjoys feeling polished and comfortable in her own skin, even after a busy day. Here are some quick hacks and timesavers that Santeramo suggests to keep yourself looking and feeling fresh, even on those busy, seemingly endless work days:

1. Does a long, stressful day drain the color from your face? Lip and cheek stain will be your savior. Santeramo recommends using Benetint from Benefit for a lip and cheek stain that stays on all day.

2. “For the woman with oily skin, primer is your best friend,” says Santeramo. The silica in primers inhibits the sebum (oil) in your face from spreading and causing an all-day shine on your forehead and around your nose. It’ll easily make makeup last twice as long. Santeramo recommends the primer from Harvey Helms Beauty. “It doesn’t have a white film and leaves the skin unbelievably smooth.”

3. Mascara rarely stays on lashes past 3 pm. Thankfully Santeramo has a longer lasting solution that won’t smudge under your eyes: “Eyelash extensions will change the way you do life.” With eyelash extensions, individual false lashes are attached to your existing lashes semi-permanently, eliminating the need for volumizing or lengthening mascara. “You’ll never wear mascara again and look bright-eyed 24/7,” she says. “All you need to do is get them filled every few weeks and you’re all set!”

4. If your skin gets just as parched as your throat, get a moisturizing and refreshing mist. Fix + by MAC is one of Santeramo’s all-time favorite products, especially for anyone who wants to keep their skin dewy and hydrated all the time. Apply the spray throughout the day to keep your skin looking fresh and to prevent cakey-looking makeup.

For those of you who want more tailored advice, StyleBee is offering a special new service where you can have a 30 minute one-on-one phone call with their creative direct, Chantelle Hartshorne. In this call she will discuss your current beauty regimen and make customized product suggestions for you to amp up your makeup routine. Sign up HERE.

About the Authors

Olga Mack 10-16Olga V. Mack, Career columnist for, is a startup lawyer who enjoys advising her clients to success and growth. Currently General Counsel at ClearSlide, she previously worked at Zoosk, Visa Inc., Pacific Art League of Palo Alto, and Wilson Sonsini Goodrich & Rosati. She is a passionate advocate for women and has founded the movement. @OlgaVMack

Katia BloomKatia Bloom is a fast-paced and strategic commercial lawyer. Currently, she is the associate general counsel at ForgeRock. Previously, she headed up legal for Avira, Inc., was a founding partner at E Squared Law Group, advising many start-up clients and was in-house counsel at Anesiva. She is actively involved in the Association of Corporate Counsel and a number of organizations promoting women in the legal profession.

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