Congratulations! You’ve built a freelance career doing work you like for clients you enjoy working with. You’re not only paying your bills and breaking even, you’re turning a profit.

But now what? If you had a 9-to-5 job, you’d be focused on climbing the corporate ladder to grow your career. With freelance, you are your own boss – but that doesn’t mean you’ve hit a ceiling. Freelancing offers endless opportunities to build and grow a small, profitable business allowing you to pursue the type of projects or lifestyle you desire

Maybe you’ve hit your stride and see an opportunity for greater growth – more clients, more work, more money. Or you’ve built an excellent reputation in your field and potential clients are approaching you with work or seeking consultation. Perhaps people want to hire you for a specific skill you excel in, but it’s only one piece of the greater problem they need to solve.

To truly help these new clients, you need reinforcements. Of course, you don’t want to jump the gun – you’re not trying to build an agency here. Rather, you’re building a small business of highly-skilled freelancers. In this post, we’ll walk through when it’s time to make your first hire, how to find the right addition to your business and resources for your next step.

When it’s time to make your first hire  

When building a freelance business, you need to make sure you can pay yourself with a manageable amount of work before you hire anyone else. Meaning, if one of your clients was to leave, you’d still be financially stable as an individual freelancer. This financial independence is a great foundation to build your business off of. Of course, it’s even better if you can afford to pay yourself and someone else in that situation, but first things first.

There are several different scenarios that signal an opportunity to grow your business, the most common being:

  • You have more quality clients coming in the door than you can manage
  • You have one or two big clients taking up the majority of your time with other smaller clients waiting in the wings
  • You’ve been approached for consulting work or speaking opportunities but are too busy with the everyday client work to accept them
  • You’re too busy with client work to focus on your personal brand and don’t want it to fall to the wayside
  • Your clients are high-margin enough to afford to bring on help with tasks that aren’t your strong suit (the financial return for the amount of time spent is high)
  • You identified a market opportunity to expand the scope of your service offerings but need help meeting those needs

The two common themes in each of these scenarios are 1) you have or could have more work than you personally have time for, and 2) you need help in areas that you’re not an expert in or simply are not interested in working in. Keep these two themes in mind as we explore who your first hire should be.

Who your first hire should be

The first role you hire for is dependent on the type of work you do and what type of business you want to grow. We often see freelancers first and foremost wanting to outsource administrative tasks such as accounting, account management, billing, taxes, contracts, etc. This is entirely understandable, as those tasks can seem boring to a creative person and it’s fairly cost-effective to hire a virtual assistant to own these responsibilities. And in many cases, hiring a virtual assistant is a great place to start in growing your business. 

However, there are many tools available that automate these administrative tasks. With the right tools implemented, it should only take you a few hours each week to complete them. Or you can bring on a virtual assistant to manage those tasks and still afford to hire someone to help with your workload. 

Instead or in addition to hiring someone to do your billing, you could hire someone to execute on client work (social media management, writing, distribution, promotion, SEO, design, etc.), build your personal brand, generate new leads, manage specific projects – things that would take you much longer to complete. And time is money.  

power is pizza

So what should you hire for instead? Here are the questions to ask yourself when determining who your first hire should be:

  • How much budget do I have available to hire someone?
  • What type of commitment am I willing to make to them?
  • What work do I enjoy doing, what do I not enjoy?
  • What’s taking up most of my time?
  • What are the lowest-return activities for my hourly rate?
  • What would make a project or campaign even better?
  • What opportunities am I leaving on the table?

By answering these questions, who your first hire should be will be clear. Hire someone who can help with the tasks that are necessary, but are taking a lot of your time and showing little return. Hire someone with complementary skills – someone who’s good at the things you are not.

Why hire a fellow freelancer?

We’re willing to bet that you became a freelancer for the freedom and flexibility – no matter what the underlying reason was. Do you really want to add the extra commitment of payroll and a full-time employee to your flexible lifestyle? Likely not. Hiring another freelancer allows you to remain agile and ready to change with the tides.

Your freelancer is going to understand that their role may change and might be a short-term commitment, as long as you’ve communicated clearly and set clear expectations. They’re also more likely to understand how you work – and how to work with your clients. Working with a fellow freelance business owner builds mutual respect for each other’s time and work. Hiring freelancers also means that as you scale your business, you can hire people with different skill sets to meet different needs for yourself and your clients.

Before you know it, you could have a fully-functioning one-stop shop in whatever area you are serving. At this point, you’ve become a trusted resource for your clients and fellow freelancers. Plus, you’ve supported fellow business owners in finding freedom in flexibility.

How to make your first hire and where to find them

Ok, so you know what role you’re hiring for and what your budget is. Before you go out searching for your first freelancer, create a short job brief. To do this, start with outlining your bare minimum needs. It might look something like this, below.

Someone who:

  • Is dependable and trustworthy and has references or testimonials to prove it
  • Is experienced working with clients
  • Is comfortable working on a deadline with a short turnaround
  • Excels in [the role you’re hiring them for] and has work samples to prove it
  • An excellent communicator – verbally and written
  • Familiar with the tools required to get the job done
  • Has a personality that’s compatible with yours

Now that you know what characteristics you want the person to have, you need to outline what the role will actually consist of. The basics being:

  • Time commitment
  • Any specific hours or dates expected to be available
  • What the deliverables will be (what exactly you’re expecting from them)
  • How their work and success will be measured
  • Duration and timeline of the project or contract
  • What type of project(s) they’ll be working on (industry)
  • The structure of the engagement (how will you communicate, how will they turn in the work, who else will they be collaborating with, etc.)

Now you should have a nearly complete job brief. All you need to add are any fun facts or tidbits showcasing your personality so candidates can get a sense of who they’d be working with, and so that you attract someone with similar values and sensibilities.

As a freelancer, you know what you’re looking for in a candidate. Now that you’re ready, we suggest doing a search for a freelancer in the CloudPeeps platform based on the skills, availability and time zone you need.


From here, you can click on their profile to learn more about their expertise and experience, as well as read references and reviews and check out their portfolio. When you’re ready, you can set up your job on the platform.

Before finalizing the engagement, it’s great to hop on a phone or video call with them to talk through some specifics, answer any of their questions, as well as ask them a few additional questions to determine whether they’re the perfect fit or not.

Have questions about hiring a Peep to help grow your business? Leave them in the comments below!

Note: Whenever you decide to retain someone to work with you, it’s important to make sure you’re setting up the relationship appropriately and following all applicable laws when determining whether the person you are retaining is an employee or independent contractor. CloudPeeps always encourages clients and Peeps to consult with legal and tax counsel to ensure they are complying with all applicable laws. It’s up to you, not CloudPeeps, to make sure you’re compliant with all applicable laws.