How to Build an Army of Virtual Sales Assistants to Help Grow Your Business

Ever since the 4-Hour Workweek where Tim Ferriss wrote about using virtual assistants (VAs) as a way to outsource your inbox – hiring virtual sales assistants has hit the mainstream.

What is a Virtual Sales Assistant?

A Virtual Sales Assistant is a remote contractor that you hire as a means of outsourcing a specific task or set of tasks in order to build a more efficient sales process.

A virtual sales assistant can also refer to a contractor located overseas. Part of the allure of VAs is they are typically more cost effective than hiring another employee locally. When integrated correctly, virtual sales assistants can become a hugely valuable asset to your SMB company.

In this article, I’m going to give an overview of how to hire, ramp, and manage a team of virtual sales assistants to help grow your business.

How To Hire Your First Virtual Sales Assistant

There are several different sites and services you can use to find VAs, but I’m only going to cover Upwork because that’s what I know best. Just do a Google search if you’re interested in testing out other services.

On Upwork, there’s essentially two 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.

Option 1: Create a Job Description and Post a Job

Your job description should be simple and to the point. Have clear tasks that outline exactly what you’re looking for.

Here’s an example:

<Sales Prospecting Coordinator Role>

Company X is seeking a virtual sales assistant with knowledge of list building and prospecting to complete tasks that are anticipated to require around 25 hours per week for an on-going duration.

The work will include the following tasks:

  • Researching target accounts and key players.
  • Using tools like LeadIQ to scrape their email addresses.
  • Using tools like BuzzSumo to build influencer lists.
  • Using tools like Google Docs & Spreadsheets to organize information.
  • Using tools like Outreach to execute outreach and manage responses.

The following skills are a must:

  • Experience with business software suites like Google and Microsoft Office.
  • Great communication skills via email, and chat.
  • Basic knowledge of project management skills; being organized is a must.
  • Some knowledge B2B sales / SaaS industry would be ideal.
  • Experience with social media a plus.

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.

Pro Tip:

A couple lines into the job post, give some instructions on how they should apply. I require VAs to use the line “Bluh, bluh, bluh, shots fired!” in 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.

Option 2: Direct Outreach to Specific 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 VAs, 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.

Pro Tip: 

Think long term. If you want evergreen value from your team of virtual sales assistants, be committed to them and they will be committed to you.

Option 3: Hire Multiple Virtual Sales Assistants at Once and See Who Rises to the Top

I would strongly suggest breaking your project up into pieces and hiring at least 3 VAs 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, spend time looking for leaders by evaluating these criteria:

  • Do they communicate effectively and follow directions?
  • If I give them feedback, do they implement it?
  • Are they eager to work on the project>
  • Do they initiate?
  • Are they attentive to details?

Option 4: Hire VAs From The Same Geographic Area

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 meetups when the team in U.S. 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!

Ramping Up Your Army of Virtual Sales Assistants

Straight up – 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.

As a side note – there’s an incredible glossary of sales terms available that you can share to get them up to speed on jargon and terminology.

Step 1: Treat Your VAs Like Every Other Team Member

Somewhere within the combination of cheap labor, English as a second language, and a lot of times never seeing the VA in-person, people think it’s acceptable to treat them differently than any other employee. It’s NOT.

It’s almost like people think they are hiring robots sometimes. This is unfortunately a sad state of affairs for outsourcing.

Treat your VAs like everyone else. 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.

Take care of them, but also realize that you’re giving them a great opportunity.

Step 2: Teach Them About Your Company’s Intricacies

Context is something that everyone wants when they are working on a new 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.

Better yet, build company documentation that you can share with them so they can refer back to it if they need to.

Step 3: Learn About Your VAs

Another great tactic is to create a quick survey for VAs to fill out. I use Typeform because it looks nice and you can create a great survey that also teaches. You can use this to learn a lot about them.

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.

How To Manage Your Army of Virtual Sales Assistants

Once fully on-boarded 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 remote 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.

Step 1: Promote your leader

Once you identify your leader, make that leader into a player-coach, responsible for the entire team’s output and also a contributing member on the projects.

You should promote that leader, double their hourly rate, and detail the extra responsibilities for the job.

Those additional responsibilities could be:

  • Creating reports
  • Grading the efforts of the other contractors.
  • 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 VAs run their questions and distribute your tasks through your team leader. This will prevent you from getting overwhelmed by questions and requests.

Step 2: Use Start, Stop, Continue

Start/Stop/Continue is a super simple way to continue giving feedback on a weekly basis. It works like this:

  • Start doing these things.
  • Stop doing these other things.
  • 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.

Step 3: Require Consistent Work Hours

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 VAs 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.

Additional Tools

I do my best to keep the VA team integrated with our current tool set so I can maintain the same types of habits in working with them.

Here’s a massive list of available tools from Sales Hacker.

Here’s a list of some of the helpful tools I personally use:

Upwork – 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 VAs and just assign them tasks through another project.

Vidyard GoVideo – Beautiful and simple screen capturing software that allows you to record videos while you share your screen and build a process.

Slack – Instant Message is super necessary for me. Slack makes it easy to shoot the shit and to answer any questions about the tasks. This is our main communication method.

Matt Ellsworth is former VP of Growth at Storefront, the Airbnb for Retail Spaces. Matt is currently Distro Partner at 500 Startups and Founder at Ellsworthy.

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