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Field Notes

Field Notes #52: How to Grow Your Content Team: Freelancer vs. Agency vs. In-House

how to grow your content team: freelancer vs. agency vs. in-house

In a perfect world, your employee roster consists of dedicated in-house team members committed to bringing your vision seamlessly to life. But in the real world, you need to constantly juggle what can and should be outsourced—and to who. (I recommend Who Not How by Dan Sullivan and Dr. Benjamin Hardy for more on this.)

For the purpose of this newsletter, I’m defining freelancer, agency, and in-house employee as follows:

  • A freelancer is a single person who works outside of your company. They are hired on a contract basis as part of a per-project or retainer relationship. They are taxed as a 1099 independent contractor.
  • An agency is a pre-assembled group of people who you hire as a vendor. Typically, there is one point of contact at the agency who is assigned to work with you and coordinates a network of employees and/or freelancers to accomplish the tasks agreed upon.
  • An in-house employee is a single person who works directly for your company under a W2 arrangement.

When considering who to hire, there is no one-size-fits-all approach. Individual company needs vary widely. While some things can never be outsourced efficiently, other things can be farmed out with ease.

Ultimately, you want to select the right person or solution who will help supercharge your content and get the results that you need.

Hiring Freelancers

As a former freelance writer, I know the perspective of an independent contractor firsthand. Now, as seasoned agency owners and professionals, we’ve hired our fair share of freelance contributors.

If you’re considering whether or not to hire freelancers yourself, here are some things we’ve learned.

1. Freelancers thrive on concrete assignments, not strategy

Most freelancers are typically far removed from an intimate understanding of a company and its products, goals, and target audience. They may be best suited to projects with clear, finite instructions.

In my opinion, freelance writers are the boots-on-the-ground execution. Sure, there are freelance individuals that will develop strategy in addition to executing that strategy, but my experience has shown me that most freelance writers do their best work with a very detailed brief.

Want high-level strategy? Seek out an agency or a freelance professional focused on strategy or other niche services.

2. Outsource complex and time-consuming tasks

Certain tasks, like link-building or “digital PR,” are well-suited to expert freelancers who are embedded in existing professional networks. 

The stuff you want to outsource is the stuff that you can’t do very well, would take a long time to learn, is expensive, or that you simply don’t want to do.

3. Vet freelancers thoroughly

Just because a freelancer isn’t an in-house employee doesn’t mean you can’t vet them the same way. Even if a freelancer comes recommended or has an impressive portfolio of work, you want to see how they perform for your company in a real-world scenario.

Have a screening call with them, ask them to share their electronic business cards to check their work portfolio, do a test project, and pay them for it. The key is to see what you’re going to get before you commit to a long-term relationship.

This helps you get a true feel for a potential freelancer’s skills and personality before agreeing to a hefty commitment. You can of course “fire” or discontinue working with a freelancer at any time, but it’s more productive to put in an effort upfront.

Tip: I wrote a comprehensive guide to finding, vetting, and onboarding freelancers. Check it out.

Hiring agencies

Are you ready for an agency? (Hello 👋🏻)

The answer may be yes—if you have significant funds to spend and have your positioning secured.

1. Dial in your core strategy

Organic content marketing builds on the fundamentals; it can’t come before your audience or core messaging work. If you don’t have your core business strategy in place, go back to the drawing board. I’m talking about:

  • What you’re selling
  • Why
  • Who you’re talking to, and 
  • What you have to say

Tip: If you need help sorting out the last bullet, check out my brand POV exercise here and here.

But if you’re early stage and don’t have any blog posts written, haven’t figured out your positioning, or are constantly changing your value proposition on your homepage, you shouldn’t hire an agency.

In the off chance we get prospects like this that slip through our initial lead qualification stage, we don’t pull any punches. Instead of selling them on services that wouldn’t move the needle, we let them know which building blocks are missing and recommend them to our partners—and, of course, encourage them to come back when ready.

2. Find your perfect agency match

Once you’re ready to commit to an agency, don’t let potential agency partners rush the matchmaking process. Just like with any relationship, go into an agency relationship fully informed and on your own terms.

If you really want to vet an agency, they’ll be OK if you slow it down and take it at your own pace. Just let them know, “Hey, we want to make sure you’re the right fit for us, and we’re the right fit for you.”

Don’t follow their sales process. You direct how you want to vet them (or us 😀).

Feel free to request that the agency contact meet with multiple members of your team, and get them to chat through more than just a blanket promise that everything will be smooth sailing once you sign. 

The right agency partner will appreciate your thoroughness as it makes their jobs easier in the long run—trust us.

Any agency that sells on simplicity is probably brushing over a lot of the details. We wouldn’t tell any client that the work we do together is going to be easy. There’s going to be some bumps in the road, and we’re going to figure it out together.

That’s why we call them agency partners.

3. Give your agency a decent runway

If you work with an agency, give them an appropriate amount of time for their strategy to take shape and the relationship to blossom.

Few people want to sign a year-long commitment to an agency they don’t know. But, you could start with three to six months to better understand how they work; then you could decide. 

Avoid committing to month-to-month. Coming from an agency perspective, it doesn’t give us the peace of mind that you’re committed to doing something long-term—and we need you involved, too. Even a few months of commitment is a better demonstration of commitment than just one, and it gives your agency team time to get in the weeds.

In order to build a truly effective partnership, consider the long game. An organic content strategy can take months or years to develop, so you can’t look for a silver bullet solution. Give your agency team adequate time for discovery and implementation.

Hiring in-house

Let’s talk about when to bring a bonafide team member on board in the form of a new W2 hire.

At Omniscient, we believe the long game often means using outsourcing options as a stepping stone until you have the time, workload, and resources to justify a new in-house staff member.

1. Technical products deserve in-house expertise 

The more complex your industry is, the better off you’ll be when it comes to nurturing in-house talent.

The differentiator between in-house and outsourcing comes down to the complexity of your industry and product. Super technical products deserve a long-term relationship with content strategists. 

As a freelancer or managing an agency—I’ve been both—it’s hard to have a short-term (like six weeks) window to come in, get to know the product really well, and develop a whole content strategy or team.

If you have a highly technical product or service, you have a few options:

  • Identify a specialized contractor who can sink their teeth into the complexities of your company and stick around for a while
  • Convert a trusted contractor or freelancer to an in-house role over time
  • Commit to a long-term (12+ months) agency relationship before you can invest in an in-house hire
  • Seek in-house help from the get-go

2. Consider moving from agency to in-house

Some of our own clients have even transitioned to hiring a full-time role because they thought that was the best long-term play. I agree—depending on the complexity of your product, this can be the best use of your budget and energy.

Sometimes a progression from one type of assistance to another makes the most logical sense. Startups can benefit greatly from hiring an agency that solidifies the strategy, then slowly hand over the reins over time.

Let’s say your company is trying to get SEO-optimized content off the ground. They already have a marketing team focused on demand generation, but they don’t have a team focused on creating new, original content. They don’t have the budget (yet).

In this case, it makes sense to hire an agency and hand that off to a team you trust. Then, over time, you can start shifting some of that responsibility in-house, where you might establish some bandwidth with an employee or get the budget for a new head count—say, with the new revenue you drive from content.

Eventually, an in-house employee might start to own the strategy creation piece, hire a couple of freelancers directly, or even bring on in-house writers to create content under their direction—ultimately replacing the agency relationship.

This is the best long-term solution and the most cost-effective. In fact, this is probably the best way for us as an agency to seamlessly off-board a client and set them up for long-term success.

3. In-house is the end goal

As the above examples and advice allude, thinking about moving work in-house is a valuable end goal in many cases.

A valid question to ask in every hiring scenario therefore becomes: Why can’t we do this in-house?

Depending on the answer, you can hire accordingly and make a plan of attack for the future.

Some of our prospects have said they don’t have time to manage the team, or they don’t have the budget to hire someone full-time to write that much content. But, if you have the money but not the bandwidth or headcount, hire an agency.

Ultimately, if an agency or freelancers can help as stepping stones on the way to success, that’s great. A good agency will understand that businesses evolve and that a company gaining the ability to hire in-house is a mark of success that should be celebrated.

Investing in the best

No matter where you look for talent or what kind it consists of, the best rule is to properly vet all candidates so that you set up your relationship to thrive.

Hard work is hard to come by

Work ethic isn’t something that only freelancers or in-house employees have. There’s no guarantee that any one individual will show up with their A-game each day.

In my experience, in-house writers can get complacent, given the output demand is less than their driven freelance counterparts.

Freelancing is like hunting—you’re “eating what you kill,” meaning that you’re always on the hunt for new clients, and that’s often through word-of-mouth. With that ethos, every freelance piece has to be the very best.

Cultivate a long-game relationship

The ultimate goal is hiring people who become skilled and self-sufficient over time, requiring little oversight or hand-holding.

Perhaps that means filtering down to your top freelancers through an ongoing series of official or unofficial test assignments. Maybe it means setting an extremely high bar for hiring criteria.

Aiming to work with people long-term prevents you from initiating substandard working relationships.

You never know when you’ll cross paths or collaborate with former hires and colleagues. When you approach hiring strategically, each and every hire becomes a part of your network, remains in your professional orbit, and contributes to the growth of your business.

Recommended Reads

  1. Who Not How by Dan Sullivan and Dr. Benjamin Hardy – This book helped us ask “Who can help us do X?” instead of “What’s the quickest way to learn how to do X ourselves?” We highly recommend it.
  2. Stop Overcomplicating It: The Simple Guidebook to Upping Your Management Game – First Round Review is always good. This piece helped me stop overthinking as a manager, and the tactics discussed apply to managing freelancers and agencies, too.
  3. Our Guide to Finding, Vetting, and Hiring Freelance Writers – “If you think hiring good writers is expensive, wait until you hire cheap ones.” Our freelance writers at Omniscient are phenomenal. This guide walks through every step we take to bring them on board.

Allie Decker

Allie is co-founder and Head of Client Success at Omniscient Digital. She previously led content initiatives at HubSpot and Shopify.