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Freelancers on the rise: adapting HR strategies for the new era

The rise of freelancing is reshaping how we think about the future of work. To dive deeper into this phenomenon, I sat down with Shannon Denton, co-founder of Wripple, for some eye-opening insights.

Alexandros Pantelakis
Alexandros Pantelakis

HR content specialist at Workable, delivering in-depth, data-driven articles to offer insights into industry and tech trends.


The statistics are clear: freelancing is on an upward trajectory. As HR professionals, you need to pay attention to these numbers. 

Shannon shared a striking finding from McKinsey’s American Opportunity Survey that finds that 36% of employed US workers identify as independent workers (up from 27% in 2016).

This surge isn’t just impressive – it’s a call to action for HR departments everywhere. You need to rethink your talent strategies and workforce planning.

But it’s not just independent studies highlighting this trend. Shannon’s own company, Wripple, has uncovered similar patterns. 

Wripple’s 2024 TeamUp report highlighted the strategic significance and growth trajectory of the freelance workforce in corporate America. Shannon comments:

“Many companies are seeking to modernize their workforce standards and practices and 92% of them indicated that they plan to increase their use of freelancers in 2024 and beyond.”

What does this mean for the HR pros? We’re looking at a future where flexible work arrangements are the norm, not the exception. It’s time to start preparing for this shift.

Economic uncertainty: The freelance catalyst

Economic downturns often spark workplace innovation. The recent uncertainties have accelerated the freelance trend. Shannon confirmed this observation:

“The increasing use of freelancers is a macro-trend that was certainly accelerated by recent economic uncertainty.”

As HR professionals, you are often tasked with balancing budget constraints and staffing needs. Freelancers offer a solution. Shannon explains:

“Engaging freelancers for short or medium-term work assignments gives companies the ultimate in financial flexibility. Companies only pay for the work they want and need to get done and no additional employee salaries are added to the books.”

Shannon has noticed that many consumer-driven sectors such as banking, travel and consumer electronics “recently turn to freelancing in lieu of hiring full-time employees.”

The appeal of freelancing: a two-way street

Understanding why professionals choose freelancing is key to your talent acquisition and retention strategies. Shannon identifies the primary draw:

“The primary driver to turn to freelancing is certainly career flexibility – being able to work (a) when you want to and (b) on the specific types of job assignments that are interesting or desirable to you.”

But freelancing isn’t for everyone. Shannon points out:

“To be a successful freelancer, you need to be an expert at something because companies want proven results and they are increasingly looking for specialists who can work efficiently.”

Shannon suggests that freelancers need to have “at least 5+ years of work experience and have mastered at least one craft or skill.  And freelancers often need financial security to feel comfortable with a non-salaried, sometimes unpredictable income.  Therefore, individuals in a dual-income family or those in the mid to late stages of their career are often the ones that turn to freelancing.”  

The freelance economy isn’t just changing how we hire – it’s changing how we think about careers altogether.

Adapting HR strategies for the freelance era

As HR professionals, you are at the forefront of this workplace revolution. Our strategies need to evolve quickly to keep pace. Shannon shared some insights on how companies are adapting:

“Companies are adapting their talent acquisition and management strategies in several key areas.”

He outlined four main areas of focus:

  • Focus on flexible hiring: Streamlining processes and using freelance platforms for quick on-boarding.
  • Creating talent pools: Building a network of go-to freelancers for recurring projects.
  • Adding tech: Using project management tools and AI for better freelancer-project matches.
  • Policy updates: Adapting payment terms and work policies to suit freelance contracts.

These changes aren’t just surface-level tweaks. They represent a fundamental shift in how we approach talent management.

But with change comes challenges. Shannon highlighted a crucial point:

“Ensuring the engagement of freelancers is handled with the same level of professionalism as full-time employees.”

This ‘professionalism gap’ is something we in HR need to address head-on. How do we ensure freelancers feel as valued and integrated as full-time staff? It’s a question that requires innovative solutions.

Other challenges he noticed are: 

  • Consistency: Ensuring quality and reliability from freelancers. Note:  freelance platforms can help with this
  • Cultural fit: Integrating freelancers into the company’s culture and brand

Technology: the freelance enabler

It’s a fact. We’ve seen technology transform this field time and again. The freelance economy is no exception. Shannon emphasized the role of emerging technologies:

“Certainly, emerging technologies are already having a tremendous impact on the world of freelance work.”

He pointed out three key areas:

  1. Freelance marketplaces and talent platforms. Advanced algorithms and AI help match freelancers with the most suitable projects based on skills, experience, and preferences.  They also offer resources, forums, and support services to help freelancers succeed and grow their businesses.
  2. Generative AI. AI is certainly impacting how freelancers work.  Increasingly, all freelancers must have a set of ‘go to’ AI tools that they utilize every single day to get their work down more efficiently with higher quality.   
  3. Virtual and Augmented Reality (VR/AR). VR/AR technologies offer immersive virtual meeting experiences, enabling more effective remote collaboration and interaction. VR/AR can create realistic training environments for freelancers, helping them acquire new skills and improve existing ones in a hands-on, engaging manner.

As HR professionals, you need to stay ahead of these technological curves. Shannon noted:

“Increasingly, all freelancers must have a set of ‘go to’ AI tools that they utilize every single day to get their work down more efficiently with higher quality.”

Shaping the future of work

Looking ahead, it’s clear that the freelance economy will continue to grow. As HR professionals, you’re not just observers of this trend – you’re active participants in shaping it.

Shannon’s insights have highlighted the opportunities and challenges ahead. But it’s up to us to turn these insights into action. We need to:

  1. Rethink our talent acquisition strategies
  2. Develop new approaches to workforce integration
  3. Update our policies to accommodate flexible work arrangements
  4. Embrace technology as a tool for managing a diverse workforce

The future of work is flexible, technology-driven, and increasingly freelance. As HR professionals, it’s your job to ensure that this future works for everyone – freelancers, full-time employees, and companies alike.

By staying informed, adaptable, and proactive, you can turn the freelance revolution into an opportunity for growth and innovation in your organizations.

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