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Rich Parker’s father worked for the same company for 35 years. That was the expectation. Stability was the social contract, and most people honoured it without question.
One generation later, Rich himself worked across four companies. The generation after him entered the workforce during a financial crisis and hit their career peak during a pandemic. And Gen Z? They’re optimising for lifestyle and flexibility from the start — not as a rebellion, but as a rational response to the world they inherited.
Now companies are waking up to a talent market that looks nothing like the one they built their hiring processes around. For Rich Parker, CEO of Plannernet, the shift is real, it’s not reversing, and the companies that treat it like a problem to manage rather than a model to embrace are already falling behind.
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Key Takeaways
- Freelancers are small businesses, not a workforce category — and companies that treat them that way make faster, smarter hiring decisions.
- The biggest internal blocker isn’t compliance or cost — it’s that nobody owns the freelance program. HR, procurement, and operations all need a seat at the table.
- Replacing a freelancer who isn’t a fit takes 48 hours. Replacing a bad full-time hire takes nine months or more.
- Companies that try to build a freelance program without end-to-end support (technology + talent pool + customer service) will struggle. Piecemeal doesn’t work.
- Freelancers entering the market need to treat it like a real business launch, not a passive waiting game.
Stop calling them freelancers. Start thinking small businesses.
There’s a word problem at the heart of the independent talent market.
“Gig economy” makes people think of Uber and Instacart. “Freelancer” carries a vague sense of someone just winging it. Neither captures what Rich Parker sees every day at Plannernet: highly experienced professionals who have made a deliberate choice to run their own business.
“Small businesses run the world,” Rich said.
“These are people who have made the choice to be a small business, not an employee.”
That framing matters more than it sounds. When companies see a freelancer as a small business: with insurance, regulatory requirements, and a professional reputation to protect, they start engaging with them properly. Clear statements of work. Defined outcomes. Mutual accountability.
When companies see freelancers as “extra hands” or temporary fill-ins, the relationship tends to go sideways fast.
The label shapes the relationship. And right now, too many companies are working with the wrong label.
The real cost of avoiding freelancers
Every company that says “we don’t use freelancers” is already paying the alternative.
Rich has a direct take on this: the cost of hiring and firing employees is significant. Finding them is expensive. Onboarding takes months. Exiting them (especially for senior roles) is a long, costly process. And there’s no guarantee the next hire will perform better.
Freelancers change the math entirely. You can bring someone in, assess the quality of work against a defined scope, and move on if it’s not the right fit. No pip. No severance. No nine-month gap in a critical role.
Rich’s company delivers a replacement within 48 hours when a match doesn’t work out. That’s not a rounding error compared to full-time hiring timelines — it’s a different paradigm.
“Why would you not look at somebody that says they have the skills, bring them in, and if they don’t work for you, you just get rid of them?”
The hesitation isn’t really about risk. It’s about unfamiliarity. And unfamiliarity is a much easier problem to solve.
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Why nobody owns the freelance program (and why that’s a problem)
Here’s a question most companies can’t answer cleanly: Who actually owns the freelancer relationship?
Is it HR, because it’s labour?
Procurement, because freelancers are technically suppliers?
Operations, because they’re the ones using the talent?
Legal, because compliance is involved?
Rich’s answer: it should be a committee — and most companies don’t have one.
“I think there’s really gotta start to be a team that works together on what your program’s gonna be. Common employees are decreasing quickly and you’d better get this team together.”
He recommends using a RACI framework (Responsible, Accountable, Consulted, Informed) to map out who owns what. It’s not a new concept — companies use it for every major business decision. But when it comes to independent talent, many organisations skip straight to blanket policies or, worse, informal arrangements that create compliance exposure.
Rich tracks over 400 compliance requirements across federal, state, and local levels in the US alone. One badly managed freelancer engagement can become a misclassification lawsuit. Most companies don’t realise how much risk lies in the grey area between “using” and “employing.”
Getting organised on the inside is what makes working with freelancers smooth on the outside.
How to Vet Freelancers Without Getting It Wrong
Planner Net has spent 35 years building a network of 3,500+ vetted professionals across 70+ countries. Rich breaks down their core vetting approach without overcomplicating it.
Experience comes first. Most of their freelancers have worked in-house at companies before going independent — they’ve been directors of meetings and events, they’ve managed real budgets, they know what a professional deliverable looks like.
Context fit matters just as much. Rich uses a vivid example: you can’t take someone used to working in Manhattan and assume they’ll slot seamlessly into a different market environment. Skills travel. Culture and work style don’t always.
And then there’s the match layer — understanding the specific client environment, the type of work being requested, and whether the freelancer’s profile actually fits what’s needed. That’s the part most marketplaces skip.
“Anybody can put out a system. But if you don’t have customer service, you’ve gotta go figure it out on your own.”
The 48-hour turnaround Rich mentioned earlier isn’t magic — it’s the product of a deep talent pool, a proprietary matching system, and a customer service team sitting in between the two sides. Remove any one of those, and the clock starts running much slower.
Generational shift: Why the freelance market isn’t going backwards
Rich has watched the freelance workforce grow from around 20 million in the US to 70 million-plus. He’s not surprised. He sees a generational logic to it.
His father worked one job for 35 years. Rich himself has had four. The generation below him entered the workforce during the 2008 financial crisis and hit their mid-career years during COVID — not exactly conditions that build loyalty to a single employer. Gen Z, Rich notes, is optimising for lifestyle and flexibility in a way that makes traditional employment feel like a constraint rather than a default.
“It’s going. It’s not gonna stop.”
His prediction: part-time employment and freelancing will continue to converge. Companies will build leaner internal teams and fill capability gaps with independent experts. The question isn’t whether to use freelancers. It’s how to do it properly before the talent you need starts treating your company as an afterthought.
The blended workforce is already here. The companies building the right infrastructure for it now will move faster than those still debating the concept in meetings.
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Tips for Success
- Treat freelancers like you treat suppliers. You switch vendors when the product doesn’t meet the standard. Apply the same logic here. Define what you need, test the fit, and iterate quickly. The cost of switching is low. The cost of inaction is not.
- Build a cross-functional team before you scale. Before you go broad with freelance usage, get HR, legal, procurement, and operations aligned on ownership, compliance requirements, and process. One bad engagement at scale costs more than setting it up right from the start.
- If you’re a freelancer, treat the launch seriously. Rich’s advice is direct: entering the freelance market is starting a business. Work that comes at you passively won’t be enough. The professionals thriving in this market are the ones who have invested in their profile, understand their niche, and show up as a business, not as someone between jobs.
