Fashion

Fearless And Flawless: Career Inspiration From StyleBee’s CEO

She took the brave step of leaving her distinguished, stable, and high-paying law firm job, and headed west to make her dream a reality.

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StyleBeeAnna Santeramo, Co-Founder and CEO of STYLEBEE, is stylish, articulate, pulled together, and highly productive. The Italian-born former New York Biglaw attorney turned Silicon Valley entrepreneur has managed to combine the productivity of a lawyer with the risk-taking of an entrepreneur. Then she added a hint of style for pizzazz! The result is STYLEBEE, an app to book beauty services (and soon products) at your home, on your own schedule.

STYLEBEE was created to address a problem many in-house counsel face: squeezing 26 hours out of a 24-hour day. When it comes to beauty services, professionals need to look polished and put together to feel confident at work, and help create the type of image clients respect. Whether we like it or not, this is particularly true for female professionals. Numerous studies show that appearance is critical for women to get promoted and advance at work. While a necessity most women would gladly do without, Santeramo realized this reality and wanted to do something about it.

Santeramo’s mission is to make these services more affordable than going to a salon and, in the process, she hopes to empower a group of women — 95% of beauty professionals are women from disadvantaged backgrounds — who traditionally have been struggling to make ends meet. Santeramo realized that she could democratize beauty services and make them both affordable and accessible through mobile technology, so she took the brave step of leaving her distinguished, stable, and high-paying law firm job, and headed west to make her dream a reality. This type of shift is one in-house counsel, who frequently are switching hats every day (if not every hour) are familiar with.

What inspired Santeramo to make such a bold move? She 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: everything around you that you call life was made up by people that were no smarter than you. And you can change it, influence it, and build your own things that other people can use. Once you learn that, you’ll never be the same again.” Though in-house counsel aren’t always comfortable being the disrupters of the status quo, Santeramo’s perspective is an invaluable reminder that all of us can have an impact within our companies and communities — even when we feel stuck or like our voices aren’t heard.

Given Santeramo’s knowledge of lawyer culture, combined with her expertise in looking professional, we asked her for her favorite beauty hacks and time savers to help cut your beauty routine in half and still look put-together in the morning.

  1. When washing your hair just isn’t an option, try dry shampoo! Dry shampoo is usually available in a spray can, but also comes as a loose powder. This talc based product will absorb any oil at your hair’s roots and create volume and lift. Women with dark hair should look for dark brown or black dry shampoos. Santeramo recommends the Batiste brand.
  1. Instead of using several different face products, use BB cream. BB creams moisturize, conceal, and blend effortlessly for light, long-lasting coverage. As a bonus, quite a few also have SPF. It’s your one stop shop for a fast skin care routine in the morning. Santeramo’s pick? “Try Gorgeous Cosmetics BB cream. It’s one of the best.”

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  1. Getting brows professionally shaped and colored “completely changes your look!” declares Santeramo.
  1. Wants curls at 6 am? Instead of struggling with a curling iron before your morning coffee, try prepping your hair the night before. Wrap your wet hair around an elastic headband at the crown of your head. Sleep on it, and in the morning you’ll have structured curls for your day.

Santeramo’s journey from law firm attorney to entrepreneur is exceptional, but in many ways she exemplifies today’s young, professional woman: she’s busy and ambitious, but still values looking and feeling polished. In-house counsel can learn from her risk-taking approach, and commitment to creating the life she wants. While all of us frequently feel too busy, we can take inspiration from her fearlessness, productivity, and — of course! — her style tips.

Olga V. Mack and Katia Bloom are startup enthusiasts who embrace the current disruption to the legal profession. Long gone are the days when in-house legal departments simply manage outside counsel or provide services. Today’s legal department is a sophisticated business unit that co-manages the company’s bottom line, embraces technology, and analyzes risks constructively. Mack and Bloom love this change and are dedicated to improving and shaping the future of the legal profession. Together they passionately collect and share inspiring stories of legal leaders who are thriving through the ongoing tectonic shift. Mack and Bloom are convinced that the legal profession will emerge from this revolution even stronger, more resilient, and inclusive than before. They are currently co-authoring a manual of the skills and traits lawyers need to succeed in — and even enjoy — today’s rapidly evolving in-house legal departments. You can reach them at olga@olgamack.com and katia@katiabloom.com or @olgavmack and @bloomkatia on Twitter.

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