How to hire freelancers and manage them at scale

By The ProcessKit Team

Here is a secret — most blog posts about hiring freelancers are written by people who have either never freelanced full-time or hired other freelancers. 

The tricky part isn’t hiring freelancers. It is hiring and managing great freelancers at scale especially if you are working with a half-dozen or more freelancers at any given time. 

Regardless of whether you are looking for PPC specialists, copywriters, social media marketers, graphic designers, or web developers, here is a guide for how to hire, vet, and manage freelancers efficiently AT SCALE without sacrificing quality or dropping any balls. 

• Get clear on the scope of the work

• How much does it cost to hire a freelancer?

  • When should I pay per hour vs. per project vs. a retainer?

• Freelancer vs. agency – which do you need?

• Freelancers vs. Employees

• What’s the best way to find and hire freelancers at scale?

  • Word of mouth referrals

  • Social media

  • Freelancer marketplaces & websites

• Interviewing and vetting freelancers

• Start with a test project

• How to manage freelancers at scale

  • Create your org chart

  • Turn repeatable tasks into processes

  • Standardize communication

  • Create reporting visibility

Get clear on the scope of the work 

Here is a quick refresher in case it has been a while since you hired a freelancer. 

If you want to streamline your hiring process, spend time doing the hard work up front, including:

• Figure out exactly what you need help with

• Write a detailed job ad that includes the full scope and sets proper expectations upfront

• Include Easter Eggs in your job ad to quickly filter out candidates that don’t follow instructions (For example, you might ask candidates to share their favorite movie at the beginning of their reply to question 4 in their application.) 
  

How much does it cost to hire a freelancer?

For most industries, you can find freelancers who charge $5 per hour or $500 per hour.
 

A good rule of thumb to follow when hiring freelancers is you get what you pay for. 

So, if you pay peanuts, you can expect to hire someone who has less experience and might need more training and micromanaging to perform the tasks you hired them to do. And, even then, the quality might still be lower than what you need. 

You should also be realistic about what your agency can afford. If you have Champagne tastes and want a best-in-class freelancer with decades of experience, but you have a Ramen Noodle budget, something is going to have to give.  

Things I learned (still learning) about hiring & delegating, from 3 phases of my career so far:

1. Freelance Delegate your own work.

2. Productized service Delegate your processes.

3. Early SaaS Delegate to collaborate & move fast.

A thread

— Brian Casel (@CasJam) March 12, 2021

Before you make any hires, you need to establish your budget. Do you have a proper Profit and Loss Statement (i.e. P&L) and know how much you can afford to spend on each project while ensuring it is profitable?

Besides establishing your budget, you should also figure out what type of freelancer you need:

• Are you looking for a strategist or consultant who can build out your strategy and/or design a process from the ground-up?

• Or someone to own a repeatable process that you or your team has already built.

• Or someone to do a one-off project with no established processes.

Depending on the type of project, this will have a big impact on who you hire, what your budget should be, pricing, etc. 

When should I pay per hour vs. per project vs. a retainer? 

Many established freelancers will have set pricing structures and processes on how they like to work with clients. 

However, it is still a good idea as the client to know your preferred processes for working with freelancers. 

For example, if you have recurring work, such as social media management, blog writing, or podcast editing, that won’t change in scope much, if at all, then a retainer agreement can work well. Many freelancers will even provide discounts in exchange for more predictable and steady work. 

Now, if you have a well-defined scope of work for something that isn’t repeatable, such as a website redesign, per project rates work better.

And, if the work is more task-based or administrative, such as a virtual assistant (VA), then paying per hour works best.  

Freelancer vs agency – which do you need?

Would it be beneficial to hire a freelancer or an agency? Or, does it even matter?

This is a thought experiment that’s worth thinking about, especially as your business scales.

Some of the advantages of working with a freelancer are:

• Cost
  When you hire a freelancer, you are hiring and paying for one person, not a team. This generally means it will be less expensive.

• Expertise
  Most established freelancers got into freelancing because they have a specialized skill that they are great at. As they work with more and more clients, this skill gets even better.

• Flexibility
  Whether it is scheduling project calls to providing feedback, it is easier to do this with one person than with an entire team. Usually. 

• Rapport
  If you work with the same freelancers over and over again, you can build a better working relationship. 

Agencies are more expensive than working with freelancers. However, the biggest benefits of working with one are: 

• Well-oiled machine
  With an agency (a great one at least), you are getting an entire team working with you. They have their own processes and systems for everything from client onboarding to project management.  

• Scalability
  You aren’t dependent on a freelancer. If Dave, the lead developer at the agency, decides to go on a week-long camping trip with no WiFi access, an agency will likely have other developers that can fill in that week, so there aren’t any interruptions or delays with the project.

• Less oversight needed
  In theory, you shouldn’t have to manage an agency as much as a freelancer because an agency has great project management systems and processes figured out. 

In addition, it is worth noting that you can often get all of the benefits of working with an agency by hiring multiple freelancers at a fraction of the cost if you have the right systems and processes in place. 

Freelancers vs. Employees

A much more interesting thought experiment to consider is whether or not to hire a freelancer or a full-time employee. 

For a remote-first agency, scaling your team with contractors and freelancers on steady(ish) retainers can be smarter than hiring full-time employees or hiring freelancers for one-off projects (i.e, the revolving door of constantly having to hire and train folks for each new one-off projects.) 

Your cost structure is more variable. 

For example, when you win a big account, it is easier to hire and get specialized freelancers up and running than a full-time employee.

Then as your agency grows, you can promote a freelancer to a full-time employee position when you need it. Since you already have trust and rapport established, you’ll spend less time hiring and training. 

In addition, with the COVID-19 pandemic creating the biggest work-from-home environment yet, this trend of remote work, variable cost structures, and talent wanting more flexibility are likely to intensify.  
 

There are a lot more A-players who specifically want to ditch the 9-5 in-office environment for  freelance, steady(ish) retainers, including: 

• Parents with young kids who don’t want to give up their career 

• Caretakers or people with chronic illnesses who still want to work but can’t go into an office 5 days a week 

• People who want to move away from super expensive cities – like NYC and SF – to be closer to family or be able to buy a home

• Digital nomads 

As Rand Fishkin points out in this blog post, it is easier to default to hiring freelancers when your agency is still small.
 

For example, if you run a full-service marketing agency with 100 employees and you suddenly bring on 10 freelance copywriters, your full-time copywriters might start to feel insecure or fearful that they are going to be replaced and out of work. There is more thought, communication, and management that needs to go into this decision when you are a larger agency. This is different from an agency that has a culture of working with freelancers since the get-go.  
  

What’s the best way to find and hire freelancers at scale? 

Once you have well-defined roles and processes, you’ll want to build a hiring funnel to consistently fill these roles with the best possible people with the exact skill sets you need.

Here are three of the most common approaches to cast a wider net and amplify your freelance openings. 

Word of mouth referrals

This is your best bet, especially if you are well-connected and have a large network in your niche. 

Not to mention, as you hire and work with more freelancers, they can also help you find additional people, assuming you aren’t a nightmare to work with and treat them well. 

There is one caveat to this approach. While you might be tempted to hire your spouse, cousin, or your best friend since elementary school, hiring family members and close friends can be problematic if you have never worked together before and aren’t great at setting boundaries. If things don’t work out, you could lose a friendship, have some awkward family reunions, or even wind up going through a divorce.  

Social media

Social media platforms, such as Linkedin, Twitter, and niche Facebook groups, can be a goldmine for finding talented freelancers.  

For example, if you run a digital marketing agency in the travel industry and you are looking for a social media marketing freelancer, you can post in some of the niche Facebook groups for travel marketing professionals. 

Freelancer marketplaces & websites

Many agencies default to hiring on large freelance job boards and marketplaces, like Fiverr, Upwork, Guru, Indeed, or PeoplePerHour. 

While you’ll likely get a ton of resumes going this route, the quality tends to be lower. You’ll need to spend more time sifting through applications. 

In general, you’ll get better results if you stick to sites and marketplaces that cater to your industry or the skills you need. 

For example, if you are looking for freelance designers, you might post on 99Designs. Or, if you need writers, you might post on ProBlogger. And, if you need a developer, you might turn to TopTal. 

Interviewing and vetting freelancers

Then, build processes for screening and narrowing down top candidates from the initial application review to the interview and the final hiring decision.  

Here are some red flags to look out for (and save you a ton of time and hassle) when interviewing freelancers:

• No processes or can’t articulate them

• No questions asked

• No work samples

• Late to the call or takes forever to respond to your messages (i.e. think not hearing anything for a week or longer)

• Makes big promises that they can’t keep, such as rank number one on Google for a competitive keyword in 30 days

• Super low rate (i.e. you get what you pay for)

• Many grammar and spelling errors

Start with a test project

Test projects are another way to reduce risks and ensure that both you and your freelancers work well together.  

This can either be framed as a one-off project, or you can turn the first milestone of a larger project into a test project. 

For example, if you are redesigning your agency’s website, you could have a designer build a lo-fi wireframe for your about page or a developer just code the about page as the test portion of the project.

This is a hedge to make sure you both work well together, and you aren’t out a bunch of money if the project doesn’t go smoothly, or the freelancer goes MIA. 

Ultimately, scaling your team works the same as any other process in your operation.  You as the founder don’t need to be involved in every step of that hiring process, as long as you’ve built a predictable process for others to manage it.

How to manage freelancers at scale 

Did you know that only 8% of companies that hire freelancers have established processes in place to manage them?

Once you have a few freelancers working with your agency, your focus should be on building out processes and workflows, so you don’t have to micromanage them or worry about the quality of work going downhill.

Create your org chart 

This might sound like overkill if you have less than 10 people working in your agency. 

However, even if you have people currently filling multiple roles or positions where you are not ready to fill yet, it is helpful for building a roadmap for the agency that you want to grow into. Not to mention, you can identify gaps early on around key positions and processes.  

Here is an example of what an org chart might look like for a content marketing agency. 
 

Pro Tip: When you are ready to bring on another full-time employee, here is a guide for how to automate the most tedious portions of the hiring process.

Turn repeatable tasks into processes  

All repeatable tasks should have processes and/or workflows that you can plug freelancers into in your agency. 

Going back to our content marketing agency example above, if you hire and manage a lot of freelance writers, it is more efficient to build a workflow with clear processes that all freelancers follow than having to create new instructions for each writer every single time you give them a new assignment.

An added advantage is that the quality of work and the likelihood of balls being dropped go way down since all of your writers know exactly what’s expected of them. 

Pro Tip: Here is how to create and automate this process using ProcessKit. 

Standardize communication 

We don’t need to explain why communicating regularly with your freelancers that you hired to complete projects or tasks is vital.

Building out processes for who is responsible for what, when to communicate, and how often can save time and minimize dropped balls, missed deadlines, or a freelancer going MIA.  

A golden rule – the more clarity you can offer around your expectations – both in terms of the level of quality and expected deadlines – the more likely a freelancer will rise to the occasion and meet or even exceed them. 

However, your communication shouldn’t stop when the project is complete – even if you don’t have any more work for them right now. 

If you keep the conversation lines open, you’ll be able to grow your freelance talent pipeline for when you do need help again. This makes it faster and easier to hire freelancers in the future. 

Create reporting visibility 

The final piece is reporting. As the owner of the agency, you should be able to see exactly where anything stands within a few minutes of logging into your project management software. 

This comes in the form of standardized workflows, reports, and dashboards covering everything from project deliverables and quality to deadlines and overall agency profitability. 

In general, this can be as simple as having key team members send you a standardized report and update once a week. For example, you might have your project manager send you an update on what was delivered for all clients this week, what will be delivered next week, and any issues that came up. 

In sum, hiring a freelancer for your agency is quite simple. 

The real work is how to hire and manage freelancers at scale. This boils down to standardizing your processes and communication.