The Secret to Finding Rockstar Freelancers on Upwork

When I first started hiring for 5Four Digital, I didn’t have a massive budget or a full-blown HR department. What I did have was Upwork—a platform with a worldwide pool of talent. Over time, I cracked the code on how to consistently find freelancers who are not just skilled but also aligned with my agency’s vision. Today, I want to share the exact process I’ve used to build a borderless team of rockstars who elevate every project.

Here’s how to find and hire your dream team on Upwork:

1. Write a Job Listing That Speaks to Top Talent

A strong job listing does more than just describe the role—it sets expectations and filters out less-qualified candidates. Start with a clear, attention-grabbing title. For instance, instead of “Looking for a Designer,” try “Experienced UX Designer with E-Commerce Expertise.”

Break your listing into these key sections:

• Introduction: Outline the role and goals in 2-3 sentences.
• Key Responsibilities: List the specific tasks they’ll handle.
• Qualifications: Focus on relevant skills, tools, and experience. Forget traditional degrees—real-world results matter more.
• Software Expertise: Mention preferred tools (e.g., Figma, Webflow) but note if they’re “recommended, not required.”

End with a call to action, like: “Please include 1-3 examples of your work and describe your role in each project.” This ensures you’re getting tailored applications right from the start.

2. Budget for Quality

Freelancers know their worth, and the best ones won’t take lowball offers. While hiring globally allows for cost savings, paying slightly above the market average for their region is a game-changer. It demonstrates respect for their expertise and builds trust from the beginning.

Pro Tip: Use tools like Glassdoor or salary benchmarks to determine fair rates, then add 20% to show you’re serious about hiring top-tier talent.

3. Use Upwork’s Metrics to Your Advantage

One of Upwork’s greatest strengths is its review system, which helps you separate the exceptional from the average. Here’s what to look for:

• $500+ in earnings: Indicates they’ve completed enough projects to prove reliability.
• Three or more reviews: Ensure there’s feedback on their work.
• 90%+ job success rate: A solid track record of client satisfaction.

When reviewing portfolios, focus on the details. Are their deliverables polished? Do their skills align with your needs? Dig into reviews to see what clients say about their communication and timeliness—two crucial factors for remote work success.

4. The Interview: More Than Just a Chat

Once you’ve shortlisted a few candidates, schedule short interviews to get a better sense of their working style. This is your chance to evaluate not just their skills but their personality and problem-solving approach.

Here are a few questions I always ask:

• “Tell me about a challenging project you worked on. How did you navigate it?”
• “How do you handle tight deadlines or unexpected changes?”
• “What tools or processes do you use to stay organized?”

The goal is to gauge their communication skills, resourcefulness, and ability to fit seamlessly into your workflow.

5. Start Small with a Test Project

A test project is your best friend when hiring freelancers. It’s a low-risk way to evaluate their skills, attention to detail, and ability to meet deadlines.

For example, when I needed a new web designer, I assigned a small, paid task to create a landing page. This allowed me to assess not only their technical skills but also their responsiveness and willingness to accept feedback. Once they nailed the test, I felt confident assigning bigger projects.

Why Upwork Works for Scaling

The beauty of Upwork lies in its global reach. With the right strategy, you can tap into a diverse talent pool, build a 24/7 workflow by leveraging different time zones, and deliver high-quality results consistently. The best part? You’re not just hiring freelancers—you’re building a network of collaborators who can grow alongside your business.

Take your hiring strategy to the next level!

P.S. Want more insights? Check out my book, Borderless, for an in-depth guide to sourcing, onboarding, and scaling with global talent.