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.”

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.”

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.

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.”

Common Questions for the Virtual Executive Assistant

In her first few months as a virtual executive assistant, Cass says the she encountered a few misconceptions about virtual executive assistants. Below is an excerpt from one of her blog posts.

Q: You’re virtual so would you come to work an event?
A: Yes! Just because I work virtually doesn’t mean I won’t leave my house. I love face to face meetings! Some clients need help arranging an event or taking registrations and sales. Working virtually means I provide all my equipment, and work independently! While you are busy focusing “on” your business I am busy in the details of your business, your blog posts are going up, your mail is getting read, and your research is getting done. Freedom!

Q: What are your rates and do you bill hourly?
A: I bill hourly, and I provide convenient packages of 5, 10, 15 and 20 hours. That blog post you needed me to do? That took 2-5 minutes. Guess how much more I can get done in that one hour for you? You don’t need a lot of hours to free up your time in a big way.

Q: I have this one task, but it is so mundane and simple, would you want to do that?
A: Bring it on! I sink my teeth into something complicated and strategic, and I love problem-solving. But combing through documents to make sure every period is in place, formatting is perfect or deleting those duplicates excites me just as much. Do you know why? Because I am creating freedom for you!

Learn more about the UCSC Extension Administrative and Executive Assistant certificate program by visiting our website.

Visit Jennifer Cass at her website to learn more.

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