One of the most persistent questions in the freelance-to-agency journey is whether clients prefer working with individual freelancers or established agencies. It’s a deceptively simple question with a surprisingly complex answer—one that impacts everything from your pricing strategy to how you structure your business.
Recently, Amy Bridges posed this exact question in the Milo Mastermind Facebook group: “Does anyone else feel like it’s easier to sell projects as a freelancer than as an agency?” Her question sparked a fascinating discussion that gets to the heart of how we position ourselves and attract the right clients.
Key Takeaways from this Episode:
– Sales success depends more on the individual doing the selling than the business structure itself—clients buy from people they trust
– Agencies typically have better client retention because teams can handle capacity issues that overwhelm solo freelancers
– Specialized, niche skills are often easier to sell as an individual, while general marketing services benefit from an agency structure
Individuals Sell, Teams Retain
Here’s the counterintuitive truth: it’s often easier to close deals as an individual, but it’s easier to keep clients as a team.
When you’re in a sales meeting, the client isn’t buying your agency structure—they’re buying the person in front of them. They’re responding to your expertise, your confidence, and the trust you build in that conversation. Clay shared his experience running an agency: “People bought because they loved me and they trusted me.”
The agency advantage shows up after the sale. When you have a team, you’re far less likely to let clients down due to capacity constraints. Solo freelancers face a common trap: they excel at sales, book multiple projects, then become overwhelmed with delivery. When that happens, quality suffers, deadlines slip, and clients drift away.
With a team behind you, work continues even when you’re sick, on vacation, or focused on other priorities. That reliability translates directly into long-term client relationships.
The Best of Both Worlds
The ideal approach? Sell as an individual while referencing your team’s capabilities.
This hybrid strategy gives you the personal connection that closes deals while building confidence that the work will be handled professionally. In your pitch, you can say something like: “I’ll personally oversee this project and ensure quality control, and my team will handle the execution.”
This approach works because it addresses both client concerns: they get the expertise and accountability of working with you directly, plus the capacity and reliability of a full team.
When Structure Actually Matters
While the individual typically drives the sale, your business structure does influence which types of clients you attract.
Some clients specifically want to work with agencies. Medium to large companies often have procurement processes designed for agency relationships. They want the infrastructure, the backup capacity, and the reduced risk that comes from working with an established firm.
Other clients prefer working one-on-one with a freelancer. They might want to avoid the red tape of vendor contracts, or they specifically value the direct relationship with a specialized expert. These clients often see agencies as unnecessarily expensive or bureaucratic.
Clay experienced this firsthand when he rebranded from operating under his personal name to an agency identity. Even though he was still essentially a freelancer, his conversion rates improved dramatically. The perception of being an agency opened doors to different types of clients.
Specialized Skills vs. General Services
Your service offering should guide your positioning decision.
Highly specialized skills often sell better under a personal brand. When you’re known as the absolute best at one specific thing—whether that’s custom animations, complex data management, or neurodivergent employee communications—clients come specifically for your expertise. In these scenarios, you hold the leverage. Your sales pitch can be refreshingly simple: “Here’s my fee.”
General marketing or design services typically benefit from an agency structure. When you offer a broad range of capabilities, clients feel more confident working with a team that can handle diverse needs and scale as projects grow.
The Premium Personal Option
What happens when clients specifically request you, even when you have a capable team?
This situation comes up frequently across all service industries. The solution is straightforward: offer a premium tier for clients who want your personal involvement.
When Clay consults with service providers—whether chiropractors or creative professionals—he recommends maintaining two pricing tiers. The standard rate covers work done by associate team members. The premium rate (significantly higher) guarantees your direct involvement.
This approach accomplishes several things. It protects your time by making personal involvement financially worthwhile. It gives clients choice and control. And it prevents you from becoming a bottleneck in your own business.
Business-to-Business Dynamics
If you work primarily with other businesses, especially agencies, the freelancer model often wins.
Agencies looking to outsource specialized work typically prefer working with individual contractors. The relationship is simpler, the pricing is more straightforward, and there’s less overhead involved in the partnership.
This B2B dynamic shifts the typical agency advantage. When your potential clients are themselves agencies, they’re not impressed by your team—they want access to specific expertise at a reasonable rate.
Making the Right Choice for Your Business
Rather than asking whether freelancer or agency positioning is universally “better,” ask which structure attracts your ideal clients.
Both models work. Both can be highly profitable. The key is alignment—matching your business structure to the types of clients you want to serve.
If you want to be known for deep expertise in a specialized area, lean into personal branding. Build your reputation as an individual expert. Focus relentlessly on your craft.
If you want to serve clients who need comprehensive solutions, build an agency. Develop systems, hire great people, and create a brand that represents quality beyond any single individual.
Whatever path you choose, remember this fundamental truth about sales: if you find yourself struggling to convince potential clients, you’re probably targeting the wrong audience. Great marketing isn’t about persuasion—it’s about finding people who already want what you’re offering and making it easy for them to say yes.
The freelancer-versus-agency question doesn’t have a one-size-fits-all answer. But by understanding how each structure influences client relationships, retention, and sales dynamics, you can make an informed choice that sets your business up for sustainable growth.
