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CEO Mark Ross recently needed to create a presentation about the organization’s products. But his firm, Dragin.io, doesn't have an internal marketing team, and he didn’t have time to create it himself. So, he hired a freelancer.
“I drew what I envisioned this deck would look like with all the words that are important and general ideas of what images I wanted,” he said. Then, Ross hired someone from the freelance marketplace Fiverr to create the presentation for a couple of thousand dollars.
“The result was excellent,” he said. “She communicated really well with me back and forth, and in a matter of a week, I had an excellent-looking, fully animated PowerPoint deck.”
Ross, who also uses freelancers to create logos, videos and other marketing materials, isn’t alone in integrating more freelancers into his organization.
In a 2024 survey of 214 organizations by freelancing platform Wripple, 92% said they plan to increase their engagements with freelancers over the next two years, compared to 42% in 2023.
More than a third of US workers identify themselves as independent workers. This includes freelancers who create their schedules, find their clients and work on their own terms.
Freelance workers can bring many benefits to organizations. However, there are some caveats to bringing them on board to ensure the experience is successful for everyone.
The Benefits and Challenges of Hiring Freelancers
Companies usually hire freelancers to access specialized skills in a more flexible, cost-effective way than hiring full-time employees, said Shannon Denton, co-founder of Wripple. For instance, a company may need specific skills or extra help for a project but doesn’t have enough work to justify hiring someone permanently.
“It’s the ultimate combination of financial flexibility and agility,” Denton said. “You don’t have fixed-cost employees; you don’t have a long-term commitment. But you get specialized talent.”
Working with freelancers also lets companies tap into expertise outside their core services and scale up and down quickly to adapt to business demands, said Jeffrey Burnett, CEO of industrial staffing company Labor Finders, which has increased its use of freelancers over the past year, particularly for shorter-term projects such as content writing and social media.
“We fill those gaps in our own business to not have fixed costs and to be more flexible and nimble, so we can manage our costs better during this economic cycle,” said Burnett, adding that many companies he works with are also hiring more freelancers.
Despite the evident benefits, companies sometimes face challenges when working with freelancers, one of them being a potential disconnect between the organization and the freelancer.
“We call it the professionalism gap,” Denton said. “Making sure that both sides have a very clear understanding of the scope [of the job], what’s expected and the deliverables is something that’s important but still not quite there in a lot of cases.”
Many companies also struggle with the independent nature of these workers and sometimes try to impose the same scheduling restrictions and management approach on freelancers as they would full-time employees, he said.
Because of their independent status, some organizations worry about being compliant with tax and labor laws, Denton says. “Even though freelancing is more common, I still hear some say, ‘We’re not sure we want to use freelancers. Isn’t that complicated with employment law?’”
Related Article: How Gig and Freelance Workers Can Support Your Workforce Strategy
How to Successfully Work With Freelancers
If you’re new to working with freelancers, Denton suggests starting with one specific area where you need extra help, such as content creation or website design.
"It’s a huge opportunity for businesses and freelance workers,” he said. But there are some steps to ensure that the relationship is mutually beneficial.
Understand How Freelancers Work
Freelance workers aren’t employees; they choose to be independent, and it’s important for companies that hire them to understand and respect that distinction.
Freelancers decide who they want to work with, set their schedules, typically work with multiple clients, use their own equipment and determine how and when they get their work done. They may be paid hourly, by project or via a retainer.
The Internal Revenue Service defines these workers as independent contractors when the company they’re working with has “the right to control or direct only the result of the work and not what will be done and how it will be done.” Freelancers receive a 1099 instead of a W-2.
Organizations must recognize these caveats when working with freelancers and not set parameters that interfere with their independent contractor status, Denton said, adding that complying with independent contractor rules is a common concern for companies.
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Earlier this year, the U.S. Department of Labor issued a new worker classification rule to help companies avoid misclassification.
Related Article: More Companies Are Hiring Fractional Executives. Here’s Why.
Set Clear Goals and Expectations
A thorough project description is the top factor for freelancers when choosing which projects to take on, according to Wripple’s report.
“If you’re using a freelancer, my advice is don’t skimp on details,” Ross said.
When working with freelancers, Ross spends time mapping out exactly what he wants, including examples. “The more time you put into preparing that information upfront, you'll just be so much happier [with the result],” he said.
While companies can’t direct how freelancers work on a project, Denton said they should offer clear descriptions of tasks and deliverables — and make sure the freelancer has access to any data, reports or other information they need to complete the project.
Make Them Feel Like They're Part of the Team
Even though they’re independent, freelancers still want to feel connected to who they’re working with to some degree, Denton said. Give them a point of contact within the organization, introduce them to other team members and invite them to meetings when it’s necessary for the project.
Being available to answer questions is also crucial for a successful freelancer relationship, Burnett said. Communicate any changes about a project that come up along the way.
“If people internally in the organization aren’t communicating regularly with you and setting clear expectations and goals, well, guess what? There's going to be problems,” he said.
Regularly checking in with freelancer workers and providing feedback is also important for building a successful relationship, Denton said.
In some instances, a company might provide a freelancer with log-ins to a shared drive or messaging tool, like Slack, which he said can help these workers feel connected. Organizations may choose different permission or security levels to grant them access to what they need while protecting other company information.
The bottom line, Burnett said, is that companies must respect a freelancer’s independence and flexibility. When you do, “They’ll take care of you,” he said.
