Trends in Freelancing in the Era of Digital Transformation

eWEEK DATA POINTS: In order for enterprises to stay at pace with the competition, they need to have a pulse on what the IT workforce looks like today and what their teams will need in 5-10 years to prepare and retain talent.


Digital transformation has been a buzzword and a reality among the enterprise community for several years, with many companies investing in cutting-edge technology to become more agile and efficient. With its potential benefits, digital transformation is not tomorrow’s strategy but is a real and critical need now. However, this transition requires specialized IT skills that are challenging to find in light of today’s tight labor market.

In order for enterprises to stay abreast of their competitors, they need to have a pulse on what the IT workforce looks like today and what their teams will need in five to 10 years to prepare and retain talent.

As an on-demand, online talent platform, Upwork has a bird’s-eye view of how the workforce is evolving. Tech is the largest category on the platform (everything from mobile development to information security and network admin), and executives are seeing a lot of demand driven by digital transformation initiatives.

In this eWEEK Data Points article, Upwork Vice President of Engineering and Product Mike Paylor offers five freelancing workforce trends to watch and what they reveal about the larger tech industry.

Data 1: Distributed Teams

At this critical moment in the talent war, “location” should not be an obstacle for hiring. According to Upwork’s Future Workforce Report, younger-generation managers are 28% more likely than their Baby Boomer counterparts to include remote workers on their teams. Additionally, with the current attempts to contain the spread of COVID-19, we are seeing early signs that this could accelerate businesses adjusting to allow for distributed work. Teams that put the right infrastructure and processes in place to be remote will not only have a competitive advantage for talent, but will be set up for success when it comes to longer term talent strategy. By not confining your business to a specific location, it opens the door to a larger and diverse talent pool, as well as unlocks more economic opportunities.

Data Point 2: Upskilling With Independent Professionals

With an evolving skills gap, enterprise companies are needing to look for unique ways to attract and retain the right talent. One way is to implement internal programs that provide current employees with education and new training to reskill. Another option is to hire external independent professionals who are equipped with the specific skills employers are looking for. Independent workers recognize that they are business owners and, as such, they are more inclined to refine and grow their skills to stay competitive. According to Upwork’s “Freelancing in America” survey, “independent professionals are twice as likely as employees to have done skills training in the previous 6 months.”

Data Point 3: An Increase in Cloud Experts

To understand what enterprises are prioritizing in terms of technology, just take a look at Upwork’s ranking of the 100 fastest-growing skills for freelancers. You’ll find that the current ranking shows that skills focused on the enterprise cloud are in high demand. This surge in demand indicates digital transformation is a real and strategic imperative for businesses. It also underscores that C-suite leaders are embracing cloud-based platforms as critical to the company. Ranking includes job listings with: Amazon Web Services (AWS) (#15), Microsoft Azure (#34) and Google Cloud Platform (#94).

Data Point 4: DevOps

Upwork’s ranking of the top 100 trending skills for independent professionals also proves the idea that in order for businesses to maintain a competitive edge, they should prioritize DevOps skills (#31) into their strategy. Today, enterprises undergoing an all-in digital transformation will need to fill this skill set and embrace the collaboration between software development and IT teams in order to produce products more efficiently and solve critical issues quicker. Ultimately, these skills pave the way for more automation and flexibility when it comes to internal business processes.

Data Point 5: Open Source

Those developers with skills in open source, .NET Core (#1) and Kubernetes (#22) are among the most sought after. This trend demonstrates that open source is being adopted by enterprises and businesses on a greater scale because many see the benefits of the technology as allowing teams to collaborate more efficiently and as a crucial tool for workflow innovation. We’re seeing open source take off even more today as people adjust work modes due to the COVID-19 pandemic. Because open-source technology is transparent in nature, it enables data to be easily accessed by workers—specifically researchers and health-care professionals to help them better understand and deal with the crisis.

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