How to Hire a Copywriting Team: Options, Tactics, and Pitfalls

Founder Jean Tang outlines the three options available for companies seeking copywriters, including the strengths and weaknesses of each approach—and why an agency like MarketSmiths is your best bet.

image of swimming pool representing the different lanes you can take when you need copywriting

In these times, when easily 97% of your qualified customers are online, the web presence and content marketing efforts of nearly every company can be powerful drivers of rich, ready-to-engage leads for strong YoY growth. 

If you are with us in accepting this new paradigm, then you’ll probably also agree that the benefits derived from great copywriting can turbo-charge your results. (If you’re skeptical, read ways to make any old website an online sales engine.) 

Of course, for many companies, the next question is a tricky one. Say you don’t have an on-staff copywriting team—or you do, and they can’t meet every internal demand. 

How will your marketing team resource this need? Do you hire (more) in-house W2 copywriters? Do you find one or two good (1099) freelancers? Do you leverage your own marketers—and somehow make it all work? 

Let’s look at each of these options in turn. 

Option 1: Hire one/several in-house copywriters (W2s)

Once you get approval for headcount, in-house copywriters are an attractive option. Yes, it’ll take time for them to ramp up. But once they do, they can align with your priorities: managing marketing assets, creating new ones, developing key internal relationships, continuing to grow their knowledge base, and building a consistent voice and tone for your brand. All of this solves a host of pressing issues.  

The very first thing is to ensure that your expectations of an in-house copywriter or content marketer are realistic. You can probably think up an amazing, robust job description for this role. Yet with shifting on-the-job dynamics, things may not get done in the tidy, productive way you’re anticipating. It’s common to have misconceptions about what can be achieved. 

  • Say you’d like your new copywriters to strategize and write your email campaigns, generate topics for and write blog posts, and manage your social channels. Sound attainable? Maybe. In reality, your in-house talent will likely find themselves dealing with multiple competing priorities, leaving deliverables to take a back seat. Long-forgotten blog posts. Sporadic social posting. Back-burnered marketing strategies: take your pick. There are going to be limits to how much your new in-house copywriters can produce, write, and scale.  This is why outside copywriters or a copywriting agency like MarketSmiths can be helpful in augmenting output—and ensuring that it stays timely and consistent
  • Every in-house marketer was once an outsider. After a few months, in-house talent risks flying too close to your company—and thereby losing that all-important arm’s length perspective. As a result, it’s easy to forget how to speak to the real outsiders: your prospective clients. Copy iterations run together. Jargon crops its ugly head. Internal copywriters grow long-winded, throwing in every last detail (along with the appropriate highlights). This is also a place where copywriting agencies have a unique advantage. Evaluating your company from a distance, agencies retain arm’s length perspective—and stick to powerful, client-centric value propositions that open minds and close sales.

Let’s say hiring an in-house copywriter is still your best tactic. There are some hurdles you’ll need to jump before you get there. 


The first hurdle? Recruitment. You’ll write and post the job ad, socialize your need, and either onboard a recruiter—or go through perhaps thousands of resumes yourself. Even with a recruiter, you’ll green light and conduct interviews, make decisions, and sell both the job and your management. 

Compile a list of wants

As a profession, copywriting isn’t typically guided by boards, or governed by industry educational or licensing qualifications. So it’s important to spell your specific requirements out clearly. 

Basic requirements include:

  • Level: Would your new copywriters be senior, junior, mid-level, or a mix? 
  • Industry: Should they be familiar with a certain industry? 
  • Format: What will they be writing on a day to day basis? Will they be focusing on a certain type of content writing, like video scripts, or web pages? 
  • Other responsibilities: Outside of writing, what will their responsibilities be? This could include performing campaign analytics, managing assets, managing external vendors (like copywriters, web designers, and SEM vendors), and more? 
  • Success: How will you measure success? 

Deepen the list—and target copywriters

We recommend you don’t stop there. Think closely about your company culture, desirable personality traits, and skills specific to this job. Sure, everyone wants a motivated self-starter that fits into their culture. But here are a few questions you might not have thought about: 

  • Pace: Is the pace of your marketing—and your company culture—quick and productive (requiring fast work and precise deadline orientation), strategic and thoughtful (requiring productive ideas and careful execution), or somewhere in between?  
  • Strategy vs. execution: Do you need creators or executors? Another way to ask this: if you had to choose only one, would you prefer that your new copywriters create strategies—or make them happen? If you had to choose one, is it more important that they contribute to your big-picture strategies, or be painstakingly attentive to details (such as your brand style guide)? 
  • Creativity vs. logic: If you had to choose only one, would you want your copywriters to be brilliant at creative right-brain concepts (think ads and taglines) or logical left-brain narratives (think blog posts and ebooks)? 
  • Reporting: Can it be tough to pin down time with your thought leaders and subject matter experts—and extract information from them? If so, you may need a particularly gifted and inquisitive reporter to chase them down and draw them out.  
  • Industry foundation: How necessary is it that they bring industry chops to the table? (This is not a trick question!) 

Consider weaknesses, too

If you already manage people, then you know what we mean by weaknesses. No one—no matter how talented—is perfect. No one can possibly meet every expectation. 

In the writing realm particularly, there tends to be an assumption that a writer is a writer (is a writer). But that’s a myth. Even the best copywriters are not endowed with a 100% comprehensive range of skills and strengths—or a 100% absence of weaknesses. Here are some examples: 

  • A certain consumer-facing copywriter is fantastic. But their knowledge base does not translate across formats and industries. When it comes to writing (say) pitch decks or sales collateral or more complex material, they can get stuck. 
  • You speak to a solid journalist. But she has no experience writing copy. (This is largely because copywriting is a whole different skill set than journalism.) 
  • You interview a strategist whose ideas make a lot of sense. Later, you find that he is not at all strong on execution. 
  • A candidate has stellar writing samples, but shows signs of being tough to work with. 
  • Another candidate seems easy to work with. But their writing samples show they’re not great at following guidelines (or the rules of grammar or spelling). 
  • Some candidates excel at the creative…but have no idea how to write more linear pieces like an ebook or PowerPoint deck. 
  • Other writers possess inexhaustible logic. But their writing is tedious to read: there’s no flash of light or life. 
  • Some writers don’t communicate (at all). Others have a case of TMI. Pick your poison.
  • Some writers are generally strong, but may be slow…which could cause a bottleneck for campaigns. 

We recommend spending some time strategizing which weaknesses you can live with, and which are flat-out deal breakers. 

Try a test

It’s often helpful to administer a small assignment to test the waters. Think carefully about how to do this: 

  • Which content format (blog posts, a web page, etc.) should you test? 
  • Will you administer the test in-person (if so, why) or remotely—and why? 
  • How will you brief them—how much should they know in advance? 
  • Who will score the test? How do you score it to be helpful but unbiased? 
  • Will you compensate them for the test? Think carefully about this one—especially if you are testing freelance writers. What kinds of candidates do you want to attract? 

Take your time. The process can be successful, but refrain from rushing: it could take you months to find the right person. 

Best of luck. If you need advice on any of this, hit us up at


Congratulations on finding and hiring great new copywriters! Now for the next hurdle: providing a thorough onboarding experience. Here are some potential activities: 

  • Listening tour: Send your new writers on a listening tour with key stakeholders in marketing, sales, and business leaders at your company. 
  • Industry primer: Give them a primer of the industry landscape—and have them do some branding homework. 
  • Inventory: Let them riffle through past and present branding guidelines, competitor audits, user surveys, and other assets that have been created over the years. You might give them a side project—to catalog past and current assets, and note pieces that require updating (or tossing!). 
  • Deliverables: Give them live assignments—what better way to get them acclimated and move forward with initiatives!

Once they’re onboarded, it’s important to take stock of management skills specific to copywriters:

1. Growth: Beyond clear communication, constructive feedback, and regular one-on-ones, it’s best if you can give your copywriters structured and unstructured ways to expand their craft. If you are not yourself a copywriter, this can be challenging to do…and you might want to seek outside help.

2. Editing: Because every good copywriter learns well through osmosis, you’ll want to apply the work of an editor that can improve on each writer’s work product, effectively reword things, and give powerful tips and tactics for improvement. Again, if you’re not yourself a copywriter, you might bring in an outside set of eyes to assist.

3. Workload: Marketing can often be feast or famine. Keep an eye on bandwidth and utilization, and help your writers to pace their workflow so it’s balanced and achievable at all times. 

4. Limits: There will be times your copywriters are too busy to handle new initiatives that pop up. You might need to manage your stakeholders to understand this, or shift priorities as they crop up. 

Whether as an alternative to hiring or a way to augment your team, it’s imperative to have a trusted copywriting agency on your speed dial to help you meet workflow demands. An agency that focuses on quality can fill gaps in your staffing needs, and scale when your initiatives come fast and furiously. 

Option 2: Hire Freelance Copywriters (1099s)

Say you don’t have headcount, or know you won’t have sufficient work to justify a full-time salaried copywriter. You can bring a 1099 copywriter on board on an as-needed basis—for a few hours, for six months, for a particular project. (There are legal limits for using 1099s—and of course labor laws governing whether or not they can be on-site.)


To narrow down freelance writers, ask yourself: 

  • Can your writers be remote or do they need to be on-site (and why)? 
  • How experienced do your writers need to be—and why? 
  • What do you need these writers to deliver—and how much of it? Will they be focusing on a certain content format, like white papers or infographics? 
  • Will you compensate them by the hour, day, week, piece, or word? (We’d suggest thinking carefully about your internal processes—and cutting out any steps that aren’t needed. The most efficient writers can charge by the piece or by time—and in doing so, perform only what’s needed to get the job done.) 
  • Should they be familiar with a certain industry? (Again, this is not a trick question. Consider the possibility that the best writer for the job can get up to speed quickly.)
  • How—and when—will you measure success? 

While freelancers offer critical arm’s length perspective, they can lack consistency. When your favorite 1099 sojourns in the South of France—and deadlines continue to creep up—you may find yourself craving the reliability of a well-staffed copywriting agency partner.

Option 3: Leverage Internal Marketers and Other Existing Staff

In a line, we wouldn’t recommend doing this. 

A copywriting agency is the best of both the freelance and in-house worlds. The agency option offers:

  • An on-demand, always available service—with no overhead and no need to recruit.
  • Writers at all levels to meet all your needs. 
  • The practiced ability to get up to speed on your company and your industry—quickly.
  • Versatility between mediums and styles.
  • Volume. 

Option 4: Outsource Work to a Copywriting Agency—and Reduce Friction

This might be news to you: there are copywriting agencies armed with writers at all times, ready to dive into the complexities of your business, uncover resonant value propositions, and turn them into effective, lead-generating copy. For projects with a tight turnaround time, the preparedness of an agency makes them an excellent choice.

As a premium copywriting agency, MarketSmiths offers the following benefits: 

  • Excellence across a range of formats—converting web copy, narrative-driven blog posts, punchy ebooks, crisp sales collateral
  • Confidence amidst complex industries and topics. (Basically, it comes down to asking the right questions, which enable us to harvest the right insights. And yes, we always insist on a kickoff conversation—that’s where 90% of the work is done!)
  • Quality. Our content strategists act as you—applying powerful strategies and flawless quality control, making your part in this process easy and seamless. 
  • Speed. We can kick your project off within a day—and we never miss deadlines. 
  • Effectiveness. Ask for examples of our ROI and other metrics. You’ll be impressed!
  • Scale. Need copy for 20 campaigns at once? We’re on it. We have the size to scale your team—and deliver what you need, when you need it. 

No more hiring headaches. At MarketSmiths, we’re committed to delivering only the words that work—and doing it repeatedly: at scale. Ready to fuel your marketing efforts with consistent, high-converting copy and content? Get in touch today.

Jean Tang

Jean Tang

A champion of high-end content, Jean is a living tribute to copywriting for humans. In 2012, at a TEDx talk, she declared her now widely viewed “War Against Bland.” The visionary founder of MarketSmiths, Jean leads her growing team to captivate, inspire, and motivate readers. She has helped thousands of global clients generate revenue from words (up to 12,000% ROI), and transformed the writing of hundreds of seminar attendees at the SXSW Interactive Festival (2014 and 2015), SXSW V2V (2014), the Small Business Summit (2014, NYC), and other venues.

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