How to build a team of virtual assistants to help grow your startup

This post is a part of Startup Edition #31 – How do you work effectively with remote teams?

Ever since the 4-Hour Work Week where Tim Ferriss wrote about using virtual assistants (VA’s) as a way to outsource your inbox and even outsourcing your dating life, hiring virtual assistants has hit the mainstream. If you’ve never heard of a virtual assistant, essentially it’s a contractor that you’re hiring to work remotely and is a means of outsourcing a specific task or set of tasks. A lot of times a VA also refers to a contractor located overseas. Part of the allure of VA’s is they are typically more cost effective than hiring another employee locally. When integrated correctly, VA’s can become a hugely valuable asset to your startup.

First off, I have to thank my buddies, Max Altschuler & Nate Gilmore. They saved me months of effort by sharing their best practices around VA’s and giving me plenty of inspiration on how to make them work as a team. I’m going to give an overview hiring, onboarding, and managing a team of VA’s in this post. There are a ton of extra details to be covered so please feel free to ask questions in the comments. Let’s get after it!

Hiring your first VA’s

There are several different sites and services that you can use to find VA’s but I’m only going to cover using oDesk because that’s what I know. Just do a Google search if you’re interested in testing out the other services. On oDesk there’s essentially 2 ways to go about hiring. You can post the job and wait for applicants, or you can browse through contractor profiles. I’ve had luck with both and I would recommend that you give them both a try.

Posting a job

When you post a job you’re going to get a lot of varying replies back. This is an opportunity to see who’s paying attention to the finer details and who’s just replying to any job post they see. A couple lines into the job post, give some instructions on how they should apply. My first job posts required the line “Bluh, bluh, bluh, shots fired!” to be the first part of the application (shout to Max A. for this trick). Any responses that didn’t include the line, I knew the contractor didn’t read all the way through the application.

Reaching out directly to contractors

I personally prefer this approach because it gives me a chance to do some research on the contractors and also it brings less noise to the process. This also means that often times you’ll be reaching out to high quality VA’s, so you’ll want to know what’s important to them. From what I have found, the two biggest pulls are full-time work (40+ hours per week) and long-term roles. Depending on what you need done, this may or may not be part of what you’re offering. We’ve got a solid team in place today because we’re committed to them and they are committed to us.

I should also mention that you can easily combine the approaches by inviting specific contractors to apply for a job posting.

Hire several VA’s for a test and look for leaders

I would strongly suggest breaking your project up into pieces and hiring at least 3 VA’s to do the same type of work for comparison. If you can’t break the job up, it’s probably still worth it to have them do the same work so you can compare their efforts. During this part of the process I spend my time looking for leaders and answering some fundamental questions about the contractors. Do they communicate effectively and follow my directions? If I give them feedback, do they implement it? Are they eager to work on the project and attentive to details? I’ve been lucky to find great leaders this way.

Hire in the same area

My man Nate is a genius for this one. Hire from the same country and better yet, hire in the same city. Give them the chance to be a part of a team locally and have get togethers when the team in US does the same thing. They’ll all be on the same timezone and they’ll reap the benefits of working as a part of team in-person.

Once the project is complete and you’ve established whom your leader is, it’s time to onboard your new team!

Onboarding VA’s

Now let’s dive into the onboarding process and how to make it a smooth process. The funny thing about writing some of these tips is that this is really just another hiring process. There are some caveats & best practices of course, but right now we’re just talking about adding more people to your team. Somehow though, people manage to screw this process up, so here are some things to pay attention to.

Treat your VA’s like humans

Somewhere along the line with the combination of cheap labor, english as a second language, and a lot of times never seeing the VA, people think it’s ok to treat them differently than any other employee. It’s almost like people think they are hiring robots sometimes. This is unfortunately a sad state of affairs for outsourcing. Treat your VA’s like humans. They are wonderful people that want to work hard, they want to learn more, and they will be incredibly loyal to you if you treat them with respect. They’ll work harder for you and you should feel good about giving them that opportunity.

Teach them about your company and learn about them

Context is something that everyone wants when they are working on a project. As you can imagine, making judgement calls on tasks is incredibly difficult when you lack context. In the beginning, take the time to teach them about your company and why it exists. I’ll often do a training call over Skype and just take them through the general info pitch on our company. As you add more to your team, it becomes overwhelming if you’re answering simple questions over and over again for 6 people. Show them the “why’s” behind your company and give them the ability to make judgement calls. We’ll talk about another solution for this later on in the post.

Another great tactic is to create a quick survey for VA’s to fill out. I use Typeform because it looks nice and you can create a great survey that also teaches. I include the company mission, some of our videos that explain what we do, and I also make sure to find out about their personal lives & families. You’ll also be wise to find out what types of skills they would like to learn on the job and what types of tasks they enjoy the most. When I created my web scraping course, the first thing I did was share it with the whole team and they were extremely grateful to learn the extra skills. Now they all know how to scrape websites as well, which means their effectiveness goes up and cost per lead goes way down. Win-win-win, Michael Scott.

Managing your team of VA’s

Once onboarded and the projects have started, it’s good to have a framework for how you’re going to work with your team. Because they are virtual and not chilling in your office, you’ll have to learn to effectively communicate and you’ll also have to reserve some patience through the process. Don’t expect to get it right out of the gate every time, there will be mistakes but you should know that already. Focus on iterating and making the process better all the time. If you over-engineer ahead of time, you’ll move slower and get less done.

Promote your leader

In the beginning of the post, I talked about finding a leader in the group. We’re going to make that leader into a player-coach, responsible for the entire team’s output and also a contributing member on the projects. What we’ve done is selected our leader, doubled their hourly rate, and detailed out the extra responsibilities for the job e.g. creating reports, grading the efforts of the other contractors, and being responsible for all project deadlines. I’ve gone as far as giving extra permissions in the account settings like work diary access so they can see how the others are working and offer help. I’ve also granted them recruiter status so that they can put out additional jobs posts for us when we need extra hands on deck. Lastly, you should have all the other VA’s run their questions and distribute your tasks through your team leader. This will prevent you from getting overwhelmed by questions and requests.

Use Start/Stop/Continue

Start/Stop/Continue is a deadly simple way to continue giving feedback on a weekly basis. It works like this. “Start doing these things…., Stop doing these other things…., and Continue doing these things…” It means that everyone is getting constructive criticism/feedback along with some praise every week. It doesn’t become a blow to morale when someone is asked to do better or eliminate something from their weekly activities.

Require consistent login times

Our team logs in together at the same time everyday. This obviously has big communication benefits but it also brings predictability to completion dates and is reassuring to the rest of your company. We ask our VA’s to login at 12 PM in San Francisco, and we’re not as worried about the end time because they all end up working their complete hours every week.


I do my best to keep the VA team integrated with our current toolset so I can maintain the same types of habits in working with them. Here’s a list of some of the helpful tools:

  • oDesk App – You can see whom on your team is online and you get to see their most recent screenshot. Rather than micromanaging, I like to use this tool to understand workflow. I’ve learned a lot by catching interesting new ways to be efficient in their screenshots.
  • Asana – We use Asana for tasks internally. I keep track of the work in progress for the VA’s and just assign them tasks through another project.
  • Quickcast – Beautiful and simple screen capturing software that constrains your video to under 3:00. I love this tool and it’s free.
  • Google Docs – Duh.
  • Hipchat – IM is oh so necessary for me. Hipchat makes it easy to shoot the shit and to answer any questions about the tasks. This is our main communication method.


In all honesty, there’s so much more to cover than what’s been said above but this should help answer some of the basic questions you might have about setting up a team. Please ask questions below if something is unclear or even if you have a question about something I haven’t covered in this post. Other than that, all I can say is that the experience of hiring an entirely remote VA team has been an extremely positive one for us. I’m a believer and will continue to use oDesk to power our outsourced teams.

This post is a part of Startup Edition #31 – How do you work effectively with remote teams?