A man sits at a wooden desk holding a pen while working at a laptop, representing freelancers.
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Hiring freelancers: What employers need to know

12 Aug 2021

Five9’s Scott Kolman discusses the blossoming gig economy and what companies need to think about when hiring freelancers.

The so-called gig economy has been growing for years but the Covid-19 pandemic may have accelerated this rise even further.

Remote working is familiar territory for many freelancers and as the workforce becomes more decentralised, hiring these freelancers could prove to be more beneficial than ever.

Scott Kolman, senior vice-president of marketing at US cloud contact centre Five9, said the pivot to freelance is here to stay for many workers and will continue to grow over time.

“Technology is continuously evolving to elevate the degree of collaboration between companies and their employees on a local, national and global scale. This helps foster the gig economy at-large because it makes it easier for freelancers to find more work opportunities and scale their services,” he said.

“People are looking for ways to work at their own pace while also having the flexibility to cater to other facets of their lives. Freelance work gives them the opportunity to do just that.”

While there are many benefits from an employee point of view when it comes to entering the gig economy, employers can be slightly more hesitant about hiring freelancers. However, Kolman said there are many benefits to hiring freelancers, especially as remote and hybrid working continues to grow.

“Freelancers can essentially work from anywhere. These workers can be dispersed throughout local regions, where customers actually live. This is beneficial for enabling companies to build relationships with their customers, and establish repeat business,” he said.

“Employing freelancers also allows for more diversity of talent. Some individuals may not be able to commit to a full-time job, but they still provide value to a company through their diverse perspectives, whether that is based on geography or life experiences.”

How companies can prepare for freelancers

While there are many benefits to hiring freelancers such as tapping into specialised skillsets, a wider talent pool and regional talent, there are also unique challenges that companies need to be aware of when hiring.

One of the biggest areas companies need to streamline according to Kolman is communication with freelancers.

“When the pandemic first started, everyone was pushed to a remote lifestyle, which made some people anxious. For some freelancers, remote work has always been a norm; but for others just starting out as a result of the current work-from-home landscape, they require more assurance and clarification on the tasks for which they are responsible,” he said.

“Just like with consumers, employees want to be heard and often prefer to connect with a real human. The human interaction that people crave isn’t going away anytime soon, so it is important to utilise technology to keep connected.”

Another area companies and freelancers alike might think about is the emergence of intelligent virtual agents, or IVAs, which is something that Five9 works with. These are are conversational bots capable of assisting humans in a variety of tasks from the IT helpdesk to HR and finance. However, unlike traditional chatbots they are not limited by a set script.

While the technology has been used by consumers through virtual assistants such as Alexa or Siri for some time, Kolman said these capabilities are now being deployed in workplace settings, which could be important not just for freelancers but for employers and full-time employees as well.

“IVAs can address many of the common questions and issues currently handled by live agents by delivering intuitive answers to frequent questions. Employees will need to understand how to this technology will impact their job such as allowing them to focus on more complex issues or areas where empathy is required.”

Advice for hiring freelancers

When companies are looking to hire freelancers, it’s important to remember the skills they need – and that goes beyond the skills required for the job itself.

Kolman said the nature of how freelancers will work with the employer mean they will need to have a combination of technical and interpersonal skills suited to the role.

“Freelancers do not always experience a traditional onboarding process like full-time employees, so they need to be able to learn and adapt quickly, communicate effectively and bring an already existing skillset to the table. Being flexible and open to work hours that may change as well as strong time management skills is also important,” he said.

“On the internal side, recruitment teams should also be upfront about payment processes and expectations when interviewing freelancers. Freelance workers aren’t typically included in traditional payroll cycles and are usually paid once their work is completed.

“Additionally, some freelancers have a personal rate of their own, so recruitment teams need to have flexible conversations with potential freelancers to determine what is most cost-effective for both the freelancer and company.”

Finally, he added that having the proper technologies and tools in place will be essential for any company looking to hire freelancers.

“Using the cloud is a smart way for businesses to ensure both full-time and gig workers are fully supported. Through a cloud solution, freelancers can log in remotely and the browser can be a starting point for delivering services while providing freelancers with an efficient way to interface with their employees and customers.”

Additional reporting by Lisa Ardill

Jenny Darmody
By Jenny Darmody

Jenny Darmody became the editor of Silicon Republic in 2023, having worked as the deputy editor since February 2020. When she’s not writing about the science and tech industry, she’s writing short stories and attempting novels. She continuously buys more books than she can read in a lifetime and pretty stationery is her kryptonite. She also believes seagulls to be the root of all evil and her baking is the stuff of legends.

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