Why Enterprises Struggle with Freelancers – Episode 17 with Rich Wilson

What’s really stopping enterprises from working with freelancers? Is it trust, process, or simply… vocabulary?

In a recent episode of The Independent Workforce, we sat down with Rich Wilson, CEO and Co-Founder of Gigged.AI, to talk about the past, present, and future of freelance collaboration — especially inside enterprise environments.

Rich is no stranger to the space. From his early days as a recruiter at Allegis Group to advising tech leaders at Gartner, he’s been in the trenches of hiring, contracting, and now, platform building.

What followed was one of the most raw, real, and practical conversations we’ve had about the shift towards independent work — and the mindset changes companies need to make if they want to thrive in this new world.

From Burnout to Blended Talent

Rich’s journey started in recruitment — “plugging in Windows XP machines,” as he laughed — and evolved into building enterprise-scale contractor programs. But after 12 years, burnout hit hard.

“I was really burned out. I hadn’t spent enough time with my family, and I realized I was running on empty. That’s when I stepped back, got curious about AI and data, and later, joined Gartner.”

It was there that the future became clear. While advising CIOs and tech leaders, every conversation — no matter the topic — eventually came back to one thing: talent.

That’s when the idea for Gigged.AI truly took shape: a platform designed to help companies fill skill gaps fast — using internal employees, freelancers, and even AI agents.

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The Real Barriers Aren’t What You Think

So, what’s stopping enterprises from hiring more freelancers?

You might think it’s trust. Or quality. Or maybe even budget. But according to Rich, the real reason is language.

“Freelancer, contractor, consultant — they all mean different things in enterprise. Not because the work is different, but because the budget categories are. The moment you say ‘freelancer,’ it triggers the wrong internal process — and that’s where things get stuck.”

In other words, it’s not that companies don’t want to work with independent talent. It’s that they don’t know how to classify it, which affects how quickly they can buy and move forward.

“If you want to get through procurement, you have to speak their language. Sometimes just changing one word — from freelancer to consultant — gets the deal moving.”

Don’t Compete with Agencies. Compete with Inefficiency.

Gigged.AI’s strategy has evolved over the years — moving away from chasing high-volume gigs to focusing on high-value, enterprise-scale projects.

“We’re not trying to be the next Fiverr or Upwork. We’re focused on quality, not quantity. Fewer gigs, but with real impact.”

This shift required not only a change in sales strategy but a repositioning of their competition. Gigged.AI doesn’t aim to replace recruiters. In fact, Rich believes recruiters are more important than ever — just not in the traditional sense.

“The recruiter role is evolving. It’s less about sourcing and more about managing relationships — becoming that trusted advisor who ensures everything runs smoothly.”

Instead of competing with platforms or agencies, Rich set his sights on a different target:

“We started competing with large consulting firms — the ones charging $2,000 a day for work that an independent expert can do just as well, if not better, for a third of the price.”

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Why Freelancers Still Get Overlooked

Despite the demand for skills, many highly experienced freelancers still get overlooked in enterprise hiring. Why? It comes down to trust and perception.

“The funny thing is, most of the time, those big-name consultants companies hire aren’t even full-time employees. They’re independent too — just hidden behind a brand.”

But when freelancers build their own brand? That changes everything.

“You’re not just a freelancer — you’re a business now. You need to talk about the value you bring, share your wins, and make it easy for companies to say yes.”

Building the “Blended” Workforce

So what’s the endgame?

Rich envisions a future where internal employees, external freelancers, and AI agents all sit within the same workflow — matched seamlessly to projects based on skills, not job titles.

“The tech exists. The blocker isn’t the software. It’s the change management. It’s helping people adopt a new way of working while they’re already running 100 miles an hour.”

That’s why Rich focuses on building small, focused pilots with departments like data or AI — places where skill gaps are clear and urgency is high. Once that proof of concept is successful, expansion comes naturally.

Final Advice from Rich

For companies:
“Be open to new models. You don’t need to choose between recruitment agencies or consultancies. There are new options out there — flexible, fast, and just as reliable.”

For freelancers:
“You can’t hide anymore. Build your brand. Post your project wins. Show people what you’ve done and how you can help. That’s how you get work now.”

Want to learn more or connect with Rich?
He’s most active on LinkedIn — drop him a message, he’ll reply (eventually).

Catch the full episode of The Independent Workforce with Rich Wilson on Spotify, YouTube, or wherever you get your podcasts. And if you enjoyed it, remember to subscribe and share!

The future of work isn’t coming — it’s already here. The real question is: Are you ready to work differently?