Building a Scalable Freelance Program: My 2025 Playbook for Leaders

By Ray Grady, CEO at Worksuite

TL;DR

The freelance workforce is no longer a tactical side bet—it’s now a strategic lever. If you’re leading a growth-stage SaaS company or scaling global operations, you need more than a few vendor contracts and spreadsheets. You need an operating system for how external work gets done. That’s what this piece is about—my firsthand playbook for scaling freelance talent without losing control, speed, or compliance in 2025.

Why This Isn’t Just a Trend

Here’s the macro view: nearly half of the global workforce is now freelance. In the U.S., that’s 70 million people and counting. This isn’t fringe. This is how work works now.

When I talk to other CEOs, the sentiment is the same: we all want flexibility, speed, and domain-specific talent—but no one wants legal exposure, rogue systems, or a compliance firestorm. And yet, too many organizations still treat freelancer management like it’s an afterthought.

Let me be blunt: if you don’t operationalize freelance work now, you’re going to pay for it later—either in fines, churn, or growth that stalls out.

What’s Broken (And How We Fix It)

In my early CRO and COO days, I lived through the pain of scattered freelance operations. Contracts in inboxes. Payments delayed. Zero visibility into who was actually working where, on what, and under what terms.

Fast-forward to today: scaling without systems is a liability. That’s why, at Worksuite, we built a platform-first approach to freelance workforce management. It’s not theory. It’s execution. Here’s what I’ve learned—and what I recommend to every executive who wants to lead, not lag.

5 Moves Every Leader Needs to Make in 2025

1. Design Compliance Into the Workflow

If “we’ll accept the risk” is part of your vocabulary, I’ve got bad news—you’re already out of compliance. The DOL, IRS, EU regulators—they’re not waiting for your internal audit to catch up.

Bake compliance in:

• Classify freelancers properly on day one
• Automate tax form collection (W-9s, W-8BENs, etc.)
• Use an Agent of Record (AOR) when needed to shift misclassification risk

This isn’t legal theater. This is operational hygiene.

2. Automate What Doesn’t Need a Human

Your talent team shouldn’t be chasing e-signatures or formatting 1099s. Those are workflows, not jobs.

An FMS—like ours at Worksuite—automates:

• Freelancer onboarding (contracts, SoW’s, tax forms, NDAs)
• Payment approvals and global payouts
• Compliance documentation and audit trails

That’s hours back every week. And fewer things dropped on the floor.

3. Centralize Your Talent Pool

If your best freelancers live in Slack threads and someone’s memory, you don’t have a program. You have chaos.

You need:

• A searchable, filterable talent database
• Project history, feedback, and availability in one place
• A way to re-engage trusted talent at speed
• I’ve seen companies cut onboarding time by 80% just by centralizing this one layer.

4. Make It Seamless for Your Teams

Scaling freelance work shouldn’t mean asking your managers to learn six tools. Your FMS should integrate with what they already use—Slack, Asana, Google Drive, NetSuite. Whatever’s in the stack, meet them there.

Integration is what turns process into adoption.

5. Act Like the CEO of a Borderless Workforce

The biggest shift I’ve seen? Smart CEOs are building their workforce like a portfolio. Blended, distributed, and tech-powered. It’s not just full-time or freelance—it’s talent orchestration.

That mindset requires:

• System-level visibility (who’s working, where, for how much)
• Compliance guardrails without friction
• A cultural shift from vendor management to workforce strategy

This is what strategic workforce transformation actually looks like.

What This Means for Enterprise Leadership

If you’re leading a company with global ambition and growing complexity, here’s your real competitive advantage: your ability to scale work, not just headcount.

And that means:

• You need platforms, not patchwork.
• You need clarity, not chaos.
• You need to treat freelance operations with the same urgency you treat GTM or product.

Because in 2025, the question isn’t “Should we use freelancers?”

It’s: Can we do it at scale—without losing control or putting the business at risk?

If the answer isn’t a confident yes, now’s the time to fix that.

Let’s build better systems. Let’s move faster. Let’s treat external work as core work—because it is.