How To Build Your Bench Of Freelancers – Episode 35 With Maari Casey

Listen now on:

The companies getting the most value from freelancers aren’t hiring faster – they’re planning better.

In this conversation with Maari Casey, you’ll learn why building a freelance bench beats scrambling for talent, how freelancers actually protect your full-time team, why AI should support (not replace) human hiring decisions, and what separates companies that use freelancers strategically from those constantly stuck in hiring mode.

Maari Casey is the Founder and CEO of Uncompany, where she’s spent the last 15 years helping businesses build smarter, more flexible teams through freelancers, contractors, and independent experts long before the future of work became a trend.

Key takeaways

• Build a freelance bench before you need one. Companies that prepare trusted talent pools move faster than those hiring reactively.

• Freelancers are a growth strategy, not an emergency solution. Use them to scale expertise, not just fill temporary gaps.

• AI should streamline hiring, not replace human judgment. The best matches still come from understanding people, not keywords.

• Flexible talent protects your full-time team. It reduces burnout, supports business peaks, and avoids unnecessary hiring and layoffs.

• Treat freelancers like business partners. Great onboarding, clear communication, and long-term relationships consistently outperform transactional hiring.

👉 Browse 70,000+ freelancers on freelancermap — find your next expert in days, not months

Deep dive

For years, companies have treated freelancers like the fire extinguisher hanging on the wall.

Something breaks.
Someone quits.
A deadline suddenly becomes impossible.

“Quick – find a freelancer!”

Maari Casey has spent the last 15 years proving that’s exactly backwards.

Instead of reacting, the best companies prepare. Instead of hiring freelancers only when they’re desperate, they build relationships before the work even exists.

That’s the idea behind what Maari calls a Freelance Bench.

Stop hiring in panic mode

One of the most interesting ideas from our conversation wasn’t about freelancers at all. It was about timing.

Most freelance hiring begins with stress.

A client leaves.
A product launch moves forward.
A designer resigns.

Now everyone is rushing.

As Maari puts it, hiring independent talent has traditionally been reactive.

Instead, she encourages companies to identify the expertise they’ll likely need months from now, build a trusted pool of specialists, onboard them once, and make future collaboration almost frictionless.

When projects arrive, the hard work has already been done. That’s a completely different way of thinking about hiring.

Freelancers don’t replace employees – they protect them

Many leaders worry that bringing in freelancers somehow threatens full-time staff. Maari sees the opposite.

She argues that flexible talent actually protects permanent employees. When business spikes, freelancers absorb the extra workload. When demand falls, companies don’t immediately face painful layoffs.

That flexibility allows organizations to scale without putting constant pressure on their internal teams.

It’s a subtle shift in thinking. Freelancers aren’t an alternative workforce. They’re part of the workforce.

AI shouldn’t replace human judgment

Of course we talked about AI. Everyone is trying to automate hiring.

Companies generate job descriptions with AI.
Freelancers generate proposals with AI.
Platforms promise AI matching.

Maari believes AI absolutely belongs in the hiring process but not where many companies place it.

AI is excellent at turning messy project ideas into structured briefs. It’s great at narrowing down potential matches. But hiring still requires understanding the nuances that never appear in a résumé.

Can this freelancer handle ambiguity?
Do they communicate proactively?
Will they fit this team’s way of working?

That’s where humans still matter. As Maari put it, AI can get you close. People make the final decision.

👉 Sign up and post a project on freelancermap to start receiving proposals from IT experts and specialists

Great freelancers communicate like businesses

One insight stood out throughout the conversation.

The best freelancers don’t simply deliver great work.

They reduce uncertainty.
They ask thoughtful questions.
They explain how they work.
They define expectations early.
They make collaboration easy.

Companies often evaluate freelancers by portfolios alone. Maari pays just as much attention to professionalism and communication. Because projects rarely fail because someone lacked technical skills. They fail because expectations were never aligned.

The workforce isn’t becoming freelance

It’s becoming blended.

Perhaps the biggest takeaway from our conversation is that the future isn’t employees versus freelancers. It’s employees plus contractors plus freelancers plus AI.

Each solves a different problem:

• Employees preserve institutional knowledge.
• Contractors provide longer-term flexibility.
• Freelancers deliver specialized expertise exactly when it’s needed.
• AI accelerates the work behind all of them.

The companies embracing this model today won’t simply hire faster tomorrow. They’ll adapt faster. And in today’s market, adaptability might be the biggest competitive advantage of all.

Tips for success

• Build your freelance bench before you need it. Identify 5–10 specialists you’d happily work with again and keep those relationships warm.

• Use freelancers to protect your team. Bring them in during peak demand instead of overloading employees or rushing into permanent hires.

• Let AI prepare the work, not make the hiring decision. Use it for briefs and shortlists, then rely on human conversations to make the final choice.