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Should you hire a freelancer or a company?

Learn whether it makes more sense to hire a freelancer or a company for your specific web design project

Most businesses don’t keep full-time web designers and developers on staff. There simply isn’t enough work to justify the ongoing costs.

When there is a need for internal support, a web developer is always the first to be hired. Developers can provide a variety of technical support, which is required more frequently than web design updates. That makes them a smart full-time investment.

However, it’s rare that even large tech companies have an in-house web designer or UI/UX professional. That’s why we’ve had the pleasure of partnering with companies such as Bloomberg, Marriott International, and DHL.

Redesigns are inevitable, but don’t happen often enough to justify the cost of an in-house designer.

Even the greatest interface designs eventually become dated. Visual styles are no longer relevant, screen sizes and resolutions change, and features become deprecated as new technology emerges.

Even then, business goals shift and eventually a redesign becomes inevitableWe’ve put together a curated before and after gallery of our own redesign projects.

If you don’t have a web designer or developer on your team, you’ve probably had to ask the next logical question: should you hire a freelancer or a company?

Should you hire a freelancer or a company?

There’s no easy answer. Sometimes it’s difficult to discern what makes the most sense for your business and your specific project. So today I’ll share a few key insights that might help you make a decision.

When to Hire a Freelancer

You should hire a freelancer if your budget is top priority on a short-term, low-risk project that doesn’t require more than one person.

Most freelancers serve as a temporary extension of your team to help execute a project quickly without a major financial investment. You won’t have to hire them full-time, pay benefits, or worry about team culture.

However, most freelancers aren’t focused on helping you achieve your business goals. They’ll usually accept your diagnosis, provide an estimate, and execute the work. They won’t uncover the deeper problems your business might be facing or the problems you’re trying to solve.

When to Hire a Company

You should hire a company if your business goals are a top priority on a large, high-value project that might require more than one person.

Most companies are hired to be strategic partners on high-risk projects that are more complex. These often require a larger financial investment and need to be executed correctly the first time. High-risk projects typically include:

  • Redesigning a marketing website that currently has excellent SEO
  • Redesigning an internal tool that your company can’t operate without
  • Redesigning a web app to increase leads & sales
  • Bringing a new digital product to market

Pros & Cons

Here’s a quick summary of the benefits (and potential risks) of both partners:


  • More risky (sick days, availability, timeline, reputation, quality, etc)
  • Lower value, price, and capacity
  • Focused on hours and scope, not business goals and outcomes
  • Single expert
  • Usually unable to offer ongoing support and maintenance


  • Less risky (multiple team members, more experience, etc)
  • Higher value, price, and capacity
  • Focused on business goals and outcomes, not hours, pages, and features
  • Multiple experts
  • Usually able to offer ongoing support and maintenance

Ask the Right Questions

Have you ever a hired a freelancer or a company for an expensive web design project and failed to see tangible business results? It’s easy to conflate a successful project with a successful outcome. If so, it’s because no one ever asked the most important questions of all:

  • how will this project help your business make (or save) more money?
  • how will this project help make your team more efficient?
  • how will this project help save your users time and effort?

Before pages, features, timeline, and budget are discussed, these are the key questions that the right business partner will ask. These questions establish an objective foundation for any project and help keep everyone focused on the goals of the project.

For example, the goal of a website redesign project isn’t to execute a successful website redesign. The purpose of a redesign is to help the business meet specific goals such as acquiring more users, making tasks more efficient, or selling more products.

Alternative Options

If you have ongoing, long-term web design or development needs, it might be worth hiring a full-time employee (or two). You’ll likely save money over time and that person will become more valuable the longer you employ them to work on your website or product.

If you can’t afford to pay out salaries and benefits, you can keep a freelancer on a monthly retainer agreement. They get consistent, reliable income and you’ll get regular updates to your website or product.

Hire the Right Partner

The truth is, it doesn’t matter who you hire as long as they make your business goals a priority. No one can guarantee results, but if your chosen partner isn’t actually focused on helping your business grow, you’re making an extremely risky financial investment.

We take pride in making this a priority at Matthew’s Design Co. and consider it one of our greatest differentiators. You’ll get all the benefits of hiring a company without the risks of hiring a freelancer.

In fact, Matthew’s Design Co. has been ranked as one of the Top 10 Best Web Design Agencies in New York by DesignRush.

If you’re interested in working with us, we’d love to hear about your project. You can share the details here to start the conversation!

About Matt Olpinski
Matt is the President of Matthew’s Design Co. and teachers thousands of freelancers how to succeed through his personal blog and newsletter.