Executive assistant sets out her shingle in the gig economy

“Now I have organization and structure and clients.”

After working as an executive assistant at a Silicon Valley tech startup for almost nine years, a place where “it wasn’t always the most positive environment for a woman,” Jennifer Cass decided to become her own boss. She launched Jennifer Cass, Virtual Executive Assistant Services and geared up to serve executives anywhere in the world. She now makes her own hours, chooses her own clients, and even gets to coach her daughter’s volleyball games.

“I didn’t have a business plan,” she says. “I just stepped out and tried to figure it out as I went along.”

Building a virtual home office

Cass works from a corner nook in her living room with windows looking out to a suburban street in Silicon Valley. Red boxes and trays from The Container Store match the décor of the home she’s lived in for nearly a decade.

“It’s the first time as a grownup that I have a color coordinated office space,” she says. “My inbox is pretty big right now.”

The envy Cass once felt for entrepreneurs and business owners has developed into a firm commitment to her own freedom. She markets her own services as providing people “the freedom to work on your own business.”

A growing number of virtual assistants

While the numbers of virtual assistants aren’t readily available, online job sites list thousands of people willing to handle the affairs of individuals and business organizations all over the world for anywhere from $8 an hour to six times that. The Online International Virtual Assistant Convention just celebrated its 13th year in existence with an honorary Virtual Assistants Day (May 18, 2018). Just a year earlier, Entrepreneur magazine described “3 Ways a Virtual Assistant is the Fastest Ticket to Growth in 2017” and in July, Inc. magazine called virtual assistants “the Best-Kept Secret of Modern Productivity.”

“It’s a really different way to work,” Cass says. “You’re not sitting at a desk waiting to work.”

A top client is a world expert on virtual reality who speaks all over the world. Cass also works for several small businesses and nonprofit organizations.

“Now I’m finally using those high-level skills that I went to (UCSC) Extension to learn,” she says.

When she looks back at her previous life, she remembers how underutilized and undervalued she felt.

“My job was making me miserable, but I was afraid to move on.” That seems like a long time ago. “Now I have organization and structure and clients.”

Of course, there are challenges in writing your own job description. You have to learn how to manage your time and juggle clients. You have to find clients who see your value and be sure you’re willing to ask for what your worth.

Educating prospective clients

There is always a lot of client education to do, Cass says. Often people don’t understand how a virtual assistant works or that executive assistants are much more than  on-demand call center. Cass has to explain her depth of experience in customer-facing skills as well as project management and scheduling. She posts a long list of skills including everything from travel arrangement and event planning to emailing, billing, contract management, customer service, newsletters, and working as a board liaison.

Cass completed the Administrative and Executive Assistant certificate program to develop professionally, something that was critical as a single mom. It made a big difference. It was at Extension where she experienced the possibilities of the profession and felt her perspective shift.

“The instructors were high-level EAs working for Silicon Valley companies, teaching and living busy, full lives. They were acknowledging that executive assistants could do more. It helped me develop a sense of leadership and gave me the personal confidence to head out on my own.”

Visit Jennifer Cass at her website to learn more about one of our exceptional graduates.

Learn more

Explore the UCSC Extension Administrative and Executive Assistant certificate program by visiting our website.

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