3 Phases Of a Winning Flexible Talent Program

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This article was originally published in Connect, Upwork’s magazine about the modern way of working. See the digital magazine to get inspired.

In this age of agile, it’s common practice for businesses to contract freelancers and agencies for help with specialized and larger projects. But now, businesses are thinking bigger. They’re asking if a single team can scale productivity and extend capabilities with freelancer help, what’s possible if teams did the same company-wide?

That aha moment came for Josh Machiz, Associate Vice President, Partnerships at Nasdaq, after he contracted freelancers to build out the company’s social media arm. Adopting freelancers proved so successful that Nasdaq grew its social media following from 20K to over 3M, launched an Emmy-award winning show, and generated millions of impressions for each client per IPO. Machiz says:

“I think more companies shouldn’t just think of using freelancers for one-off projects. But to build long-term relationships with talent and think of freelancers as a strategic resource that can enhance their business.”

But scaling use takes more than asking everyone to contract more freelancers. Companies that scaled successfully, such as Microsoft, GE, and Airbnb, learned that doing so requires a flexible talent program.

By adopting a programmatic approach, they shortened ramp-up time for every employee and realized higher work quality, consistent employee satisfaction, and greater ROI than businesses that took an ad-hoc method.

The same businesses also learned that a winning talent program requires collaboration with key stakeholders, skillful communication throughout the company, and dedicated resources. 

Yes, it takes some work, but the returns are worth the effort. 

Rewarding results

When the head of global procurement at a multinational pharmaceutical company set out to build a talent program, they asked Upwork for help. The company wanted to drive cost savings and gain access to highly skilled talent in a manner that maintained compliance and reduced risks.

We aided them in designing a 3-month pilot where 41 internal users completed 88 projects. The 25 categories represented include graphic design, translation, and video production. The results:

  • Reduction in time to engage talent: 18%
  • Average time to engage talent: 7.7 days
  • Cost savings: 85-93%
  • Average project satisfaction score: 5 out of 5

After the fruitful pilot, the company hired two full-time program advocates. Their sole purpose is working with division heads worldwide to utilize more freelancers and agencies on Upwork.


There are many ways to build and expand a flexible talent program. Keep in mind that it’s not only about adopting but also implementing and socializing a process.

The framework Upwork uses involves a three-phase process. It was developed from years of analyzing best practices from existing clients that successfully scaled flexible talent.

Taking a phased approach enables your organization to work out details early on, which will help teams scale the program smoothly. And rolling it out in this way allows everyone to engage critical support at the right time and in a targeted way.

This process removes the guesswork around working with flexible talent and helps avoid common pitfalls that can occur with launching and growing a flexible talent program. It’s used by Fortune 500s, but the process applies to any company, whether your teams actively use freelancers now, or are considering it.

You can get a copy of the framework by downloading How to Build and Expand a Flexible Talent Program. The guide shows you how to efficiently build, measure, and scale a program to meet your business goals and optimize ROI. 

You can get a copy of the framework by downloading How to Build and Expand a Flexible Talent Program. The guide shows you how to efficiently build, measure, and scale a program to meet your business goals and optimize ROI.


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Samantha DeStefano


Samantha DeStefano is senior director of enterprise sales at Upwork, with a focus on large accounts. Prior to joining Upwork, she led regional sales teams… more