Should You Hire a Virtual Assistant?

If you're nervously thinking of handing your tasks (and inbox!) over to a complete stranger, don't worry - we did the research for you.
Should You Hire a Virtual Assistant?
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Magazine Contributor
4 min read

This story appears in the October 2020 issue of Entrepreneur. Subscribe »

It was 6 a.m., and Ari Meisel was half awake at an airport gate, about to board a flight to Toronto. Then his virtual assistant sent him a message: “Flight canceled!” it said. “We rebooked you on a different one, so head over to gate G7.” 

Meisel runs a business coaching service and productivity method called Less Doing, and this is exactly why he loves having a virtual assistant (or VA). Someone fixed his problem before he was even aware it. “I believe VAs should be utilized for personal tasks as much as business tasks because they both take weight off the entrepreneur’s mind,” he says. “I have four small children, and I’ve had VAs do all their school forms, health forms, insurance, camp registrations, etc., literally saving me hours and hours.”

Related: Is a Virtual Assistant the Secret to Keeping Your Small Business Afloat?

Many people agree. When entrepreneurs need help with tasks but don’t have the cash to hire a full-time assistant, they’re frequently getting a VA — a remote worker to handle a wide range of tasks. They can be hired through freelancer platforms like Upwork or Fiverr, but an increasing number of startups are now offering a suite of VA services. All you have to do is sign up, and the platform provides assistants and manages workflow.

COVID-19 created a new jolt for the VA industry. “The number of people working at home has revitalized these services,” says technology analyst Rob Enderle. Workflow expert David Allen, author of Getting Things Done, says it’s a response to entrepreneurs’ more hectic work experiences — now juggling kids at home and the new challenges of remote work. “Many of the things that never used to demand your attention are demanding it now,” he says. “You have to appropriately engage with the things that require your attention.”

So how useful are they? I put a premium service called Delegated (formerly known as Red Butler) to the test. I last tried a service like this in 2015, and I was unimpressed then. Workers could only perform basic tasks, didn’t understand my needs, and would disappear for days. 

But as I discovered, the VA experience of 2020 is vastly improved.

Related: 4 New Apps to Help You Manage Your Inbox

Delegated connected me with a VA named Jason, who was clearly trained in communications. He engaged daily on Slack, understood Trello, and took over my work email to make sure I communicated with people in a timely fashion. Once, during a particularly hectic period, he rescheduled a series of meetings and helped me conduct research.

Delegated, like some of its competitors, also offers productivity tools to make the most of my assistant. It helped me create task lists, use project templates, and manage my hourly costs. That last part is the biggest catch: All this productivity does have a price tag — and Delegated’s starts at $420 a month. So the question for every entrepreneur is, What’s your time really worth?


The Virtual Ladder: 3 services to match 3 different needs

BASIC: ChatterBoss

Website: chatterboss.com

Price: $25 per hour for administrative services

Handles simple duties like scheduling and email. Manages your existing process. Offers plans to become part of your team, use Slack, and develops a new process.


ADVANCED: Double

Website: withdouble.com

Price: $40 per hour for tasks and projects

Performs complex tasks and projects. Offers project templates for you and the assistant. Matches you with a VA who has a similar work style and personality.


POWERFUL: Delegated

Website: delegated.com

Price: $45 per hour for team integration

Works with your team on Slack and in Trello. Checks your email for you. Reschedules appointments and can make sales phone calls.

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