Building a Non-traditional Team – Gig Economy Freelance Future

Gig Economy Non-traditional Freelance Teams

Table of Contents

  • Jeff
  • October 17, 2019

In a day and age of seemingly limitless technology resources and a flourishing gig economy, many of us tend to be products of our environment. In early 2019, I found myself with some unanticipated turnover on my team that brought me to an impasse. At around the same time, I had received an invite from Upwork to attend their conference: #workwithoutlimits. It was at this conference that I learned about how other professionals were breaking conventional wisdom to build a virtual team of freelancers to facilitate all the demands of an in-house team. Some individuals on the panel took more of a hybrid approach, while others went all-in.

I realized that this otherwise disruptive situation for my team might just have created an incredible opportunity. Here are some of the things I’ve learned along the way when I created my hybrid team.

Ease of Use

The longer someone is in a role, the more nuanced and niche responsibilities they handle. Think about your role when you started, would the same job description work today? While you can repurpose some of the previous qualifications, in many ways, the role is unique and new. It needs a more specific individual. A purple squirrel. A unicorn. But let’s face it, that isn’t your concern! There’s not much easier than to coordinate with talent acquisition to publish the role, source these unicorns, and make yourself available to interview them.

Now let’s look at using freelance in a platform like Upwork. Like many things in life, lack of preparation leads to frustration. I started first by breaking apart the role into individual tasks to identify the skills and the types of freelancers I would need. Interestingly, I wasn’t looking for a unicorn anymore; I was looking for a few specialists that could perform a specific task. Sure it required a little more upfront effort, but the talent became very easy to source!

Time to Fill

I think it’s safe to say that we all experience similar time-to-hire windows. The less specialized, the faster the find. The more dynamic the skillset required, the longer it takes. Assuming you want to interview five candidates before making a decision, it’s likely that you’ll take up to 6-weeks to interview and make an offer. If your candidate accepts, they will likely give a 2-week notice to their current employer. That puts your time to place at roughly 8-weeks provided that everything has gone smooth.

When it comes to bringing on a freelancer, because process AND mindset are so different, everything flows much quicker. As a first-time user, managing the process myself, here’s my task list:

  • Break the role into tasks and associate tasks to niche roles
  • Craft job descriptions for each niche role with detailed expectations
  • Create an account and post job descriptions
  • Search freelance database to invite talent that could be a good fit
  • Review all applications and interview
  • Hire your team!

This entire process took me about 2-weeks. 2-weeks?! Yes, 2-weeks.

On-board and Output

Typically, when going through traditional internal hiring, I expect to have a person fully running in 4 to 6 months. By breaking apart the role into tasks and assigning those tasks to individuals, the ramp time was significantly expedited. It took 3 to 4 weeks to have the entire team up running and producing. Going into week 5, there were some additional adjustments that needed to be made. By the time we got to week 6, our output was better than it had ever been, and I was beginning to add more responsibilities to individual contributors.

Limitless Scalability

Breaking roles into tasks and not hiring someone for a full 40-hour workweek (yet), not only makes this much more affordable, but also scalable. Now that normal daily production was in a flow; I could start focusing more on special projects. This allowed me to develop a team of people that I hadn’t considered in the past. Researchers, writing specialists, editors, design support, and more were all added to my virtual team.

Similar to the process I mentioned earlier, spend time on those descriptions to be as specific as possible. The more detail you give, the higher the likelihood of success. Most of the skills and talent I need as a Director of Marketing can be found on Upwork.

The Necessary Tools

Lacking vital tools to facilitate project management, transparency, accountability, and communication will result in much frustration. Just like with any new employee, I followed an on-boarding process that would get them acquainted with the tools and technology we’d be using as a team. Your tech hub doesn’t need to be expensive or complicated; it just needs to work. Here are the tools that I’ve used so far to keep it all together.

  • Communication: it’s vital to have an accessible and straightforward software to collaborate. Since my company has Office 365, I have access to Microsoft Teams. Microsoft Teams behaves similarly to Slack. You can create teams and channels to limit distraction and silo communication.
  • Video Conference: much of this depends on who I’m connecting with and their internet connection. Microsoft Teams tends to work well, but can be spotty. Skype and Zoomare much more stable when trying to hold a conversation and facilitate a screen share.
  • Project management: there are TONS of project management tools in the marketplace. I’ve tried several. Asana seems to be the platform that people acclimate to the easiest. It’s intuitive, simple, and powerful. With a low paid subscription, we can customize fields to help organize our editorial calendar and special projects.
  • File sharing: again, depending on the access my freelancers have, we use OneDrive and Sharepoint from Office 365, and when there needs to be greater flexibility, we resort to Google Drive.

In the end, it’s my responsibility to keep projects moving and remove any friction my freelancers may be experiencing with technology. 

Standout as an Employer

How to be a rockstar in the eyes of your freelancers? Treat them like you would the new hire that would be sitting in your office. Invite them into planning meetings, ask for their opinions and perspectives on projects, and be supportive of their professional development. Learn about each freelancer, what motivated them to get into freelancing, and what their goals are in the future.

For those that are using freelancing for additional income, I ensure that not overloading them with projects. If they’re good at their job, I want to keep them happy. If there’s more work to be done, I can find another freelancer. For others, they’re using this relationship to learn more about marketing than they could in their local markets. When this is the case, I try to include them on projects that will grow their knowledge base to assist them.

My next challenge with my freelance team is to coordinate a VIRTUAL TEAM MEAL. While this will be a bit challenging having people from all over the world… I’m confident I can make it happen.

Remember, these are people that are in the pursuit of a healthy work-life balance that will sustain their lifestyle. They’re not body count to be consumed. They’re not a piece of software. They’re not going to stay if they don’t feel valued. If you treat them how you’d want to be treated, you’ll do just fine.

If you get the opportunity, I would HIGHLY recommend looking into creating a hybrid team using the freelance community. It’ll take your work to the next level.


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