How To Quickly Develop Your Workforce and Overcome AI Skills Gaps
Freelancers are key to overcoming AI skills gaps and getting ahead of your competitors—learn how to hire for skills like the most innovative companies.

If you’re feeling that your company is falling behind the competition in its adoption of artificial intelligence (AI), you aren’t alone. Recent data from The Upwork Research Institute shows that nearly half of the 1,500 global business leaders surveyed feel that most of their workers aren’t ready to work with AI. These leaders report that a mere 25.3% of their workforce is ready to operate alongside AI technology, and that even fewer workers can proactively apply AI solutions.
At the same time, 85% of business leaders are already requiring or encouraging their workers to use AI on the job—but aren’t realizing the expected boost in efficiency. The good news? The reasons (and solutions) are manageable.
Understanding the AI skills shortage
The problem is twofold. First, adding AI into an inefficient process can exacerbate problems, not make them better. Second, upskilling a workforce to use AI effectively as part of a complete digital transformation is easier said than done.
Most businesses can’t stop work for the weeks it would take to complete an AI training program. And when organizations do institute AI-related skills development initiatives, already-busy workers can be left feeling more exhausted than ever. Burnout is rampant among workers who are struggling to adopt new technology while meeting increased productivity targets.
But the pace of AI development isn’t slowing down—so a slightly late adopter to AI tech can suddenly find themselves on the wrong side of a massive knowledge gap, scrambling to reskill while keeping pace with competitors
It’s only going to get more intense, too. I expect that the way people discuss AI is going to be different six months from now. Instead of discussing the best ways to leverage out-of-the box generative AI tools for productivity, we’ll be figuring out how to deploy customized AI agents alongside human workers. The list of new skills a team needs to master keeps getting longer.
There is a solution, though—one that our research shows the most innovative companies already know.
How work innovators overcome AI skills gaps
The companies that have seen the most success in AI adoption are true work innovators. These companies aren’t facing fewer challenges, or a different set of challenges, than other businesses. They’re still facing the rapid evolution of technology, economic factors, fluctuations in the hiring market, and more.
But work innovators take a different mindset to these challenges than many other companies. Rather than focusing all their energy on external solutions to challenges, they look inward.
First, they identify what must change internally to achieve certain goals or overcome new barriers. Then, these innovators address what’s needed to make that happen: from increasing hiring to investing in technical skills training or combining two departments for better collaboration.
As a result, work innovators are flexible and open to adjusting the way they currently operate. We repeatedly see that the most innovative companies:
- Are open to distributed, remote work if it allows them to build the best team of AI talent
- Continually work toward breaking down silos across their organizations
- Make continuous learning part of their culture with ongoing programs to train employees
- Adopt a cycle of innovation that continually pushes them out of experimentation phases and into adoption of emerging technologies
But there’s another common factor among work innovators that’s most critical of all: freelance talent. The most innovative companies are using freelancers strategically in ways that help them adopt AI faster and more effectively than their competitors.
Why freelancers are key to closing skills gaps
When you hire a freelancer who specializes in AI, you’re hiring someone whose business it is to stay on top of the latest machine learning technology. You can find skilled freelancers with AI skills in all industries, from broad AI consultants to pros with experience using a specific AI tool you want to integrate into your systems.
Want to learn how to use AI agents to help your customer service team handle emails faster than ever? Interested in adopting an AI editing tool in your marketing workflow? Curious how natural language processing could help your company improve output during peak seasons? There are freelancers who help with all of these things—and more.
You don’t even have to know exactly what you want out of AI when you hire a freelancer for the first time, either. Working with a freelance consultant is a great way to understand how AI can best help your company, where you need to make process changes, and what the implementation process will look like in terms of both time and money.
Engaging the help of freelancers with specialized skill sets has lasting effects, too. You may think you’re hiring a pro to help you build a custom AI chatbot—and you are. But this decision also:
- Helps your organization identify what’s next on the AI horizon in your industry and adopt it faster than key competitors
- Allows you to move more quickly out of the experimentation phase of AI adoption and formalize its use as central to your organization
- Creates space for your team to engage in continuous learning and upskilling as well, without falling behind in your market
- Lets you continually bring in new talent who can provide additional insights and support as your projects evolve
You don’t need to reinvent your entire hiring strategy to see the benefits of working with freelance professionals who are AI specialists, either—you just need the right partner in finding great talent.
Hire freelancers like a work innovator
Managed services allow companies to find and hire specific freelance talent quickly, while minimizing time spent on administrative HR work.
Previously, finding a freelancer may have meant running several ads, scouring your networks, and reviewing countless resumes and portfolios. But today, the existence of managed services solutions (including those that leverage the power of AI!) makes it easy to hire for specific skills—all while a trusted partner handles the task of finding freelancers and helps you scope out a project.
Close your AI skills gaps with help from Upwork
Sign up to connect with freelancers you find in our AI Services hub, or get in touch with a member of the Upwork Enterprise team to discuss managed services options for your business. Because whether you’re ready to close your biggest AI skills gap right now or want help finding the right freelancers for your projects, you don’t need to go at it alone.











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