What Should I Look for in Hiring a Copywriter?

March 12, 2019


Join me on Instagram

It's great to have you here! As a seasoned business coach, consultant, mentor, and motivational speaker with over 20 years of experience, I'm excited to share my personal and professional insights to help you on your entrepreneurial journey. Let's get started!

Hi, I'm Jennifer!

Want to find a great copywriter to help sell your service or product to your ideal customer? Are you wondering where to find a copywriter for your business? And what to ask the potential hire?

If you need someone to write your website copy, craft killer email newsletters, or dream up engaging social media posts, you’re in the right place.

This post is your guide to finding the right copywriter.

So, what are you looking for?

In my opinion, the perfect writer for your business is:

  • Skilled in his or her craft
  • Confident writing about your service (and maybe even has prior experience writing on similar topics)
  • Comfortable with the kinds of writing you require, like attention-grabbing Facebook posts, an engaging email marketing series or long, well-researched blog articles
  • Someone you enjoy interacting with, who also “gets” your voice

Here’s how to make sure your new copywriter is all of those things:

Do they have the writing chops?

There are two main ways to evaluate this:

  • writing samples;
  • and a test project

Ask for writing samples of the kind of work you need to have done. 

If you’ve written your own copy that you need to have edited, ask for before and after edits that the copywriter has completed for other clients.

Need an email marketing campaign, landing page, website copy, blog, or social media post content?  Ask them to send you one from their portfolio and also ask that they include samples that are in a similar tone to the voice you’re looking for (corporate and high-brow or casual and funny), or with similar subject matter (fitness, finance, fashion, coaching, beauty, etc.) 

You may also choose to give your potential hire a quick, paid test project with a deadline. Offer some compensation (for example, half of the writer’s hourly rate) to complete a short paragraph rewrite for you. The paid bit lets the copywriter know you’re a serious prospective client and value their time. Plus, you’ll get to test out how the copywriter handles deadlines. You’ll also feel whether communication between you feels smooth and clear or strained and off.

And as you can probably tell from the ideas above, part of this interview process should be you asking the copywriter how experienced and comfortable they are with the kinds of writing you require.

Voice Fit / Subject Matter Comfort Level

The copywriter who’s most comfortable creating bubbly lifestyle articles for teenaged girls likely won’t be the best fit for a car-detailing service going after muscle car owners.

From the copywriter’s samples or writing test, (and heck, even from their emails), you’ll determine if their writing style can match the voice you’re looking for with your projects.

And be sure to communicate the tone of voice you’re going for, who your ideal client is, and other sites/businesses whose website copy resonates with you.

Here are a few other things that are easy to overlook, yet critical that you communicate:

  • How Often Do You Need Copy and What’s the Turnaround Time? Do you need daily posts on social media? Monthly email marketing newsletters? New website copy up in time for the event that’ll bring lots of traffic to your site? Make sure to let the copywriter know. And how far in advance would you like those things delivered?
  • How Many Rounds of Revision Are Allowed? A great copywriter will help you tweak what they’ve written until it feels just right. But more rounds of revision means more billable time on their end. If you’ve worked out a “flat fee” per blog post payment arrangement, for example, ask how many rounds of revisions are allowed for that price.
  • How Will Payment Work? Is your writer on a monthly retainer to complete all of the work you require, whenever you need it? Do you have a one-time website copy overhaul job where you’ll pay half of a flat fee as a deposit and the rest upon completion? Will your writer bill you hourly? And when is payment due?
  • What’s the Objective? A good writer will ask what outcome you’re looking for from the copy they deliver. Maybe it’s people getting onto your email marketing list. Perhaps you want your business’ Instagram followers to book a particular service this week. Maybe you’re looking to hook a potential customer and get them to book your service for the first time. Knowing your objective will help your writer deliver copy you love.

How to Hire a Copywriter through Upwork

Finally, if you’re looking to hire a copywriter, I recommend looking on Upwork. (I’m not an affiliate, by the way – just a fan!) Never heard of it? “Upwork, formerly Elance-oDesk, is a global freelancing platform where businesses and independent professionals connect and collaborate remotely. Upwork analyzes your needs. Our search functionality uses data science to highlight freelancers based on their skills, helping you find talent that’s a good match.”

  • Its escrow system of payment protects both the companies who hire out jobs and the freelancers who use it to find work.
  • Your (free) job posting will be instantly find-able by top quality writers, and writers at every price point, from all over the world. And if you’d like, you can choose a writer who’s in your neck of the woods.
  • You can compare the price quotes, writing samples, and even past client reviews of everyone who’s applied to your copywriting job. Those previous client reviews are a big deal, by the way. Super helpful.
  • You can create a contract (with milestones if you’d like), communicate with your writer, send files back and forth, and handle payment all on the site.

You can also work with the Dear Jenny Creative Studio team for your copywriting projects. Click here to schedule a complimentary Dear Jenny Creative Studio consultation.

+ show Comments

- Hide Comments

Add a Comment

Leave a Reply

Your email address will not be published. Required fields are marked *

More Faves 


Get the right people to listen and start taking action. The Brand Clarity Workbook is designed to help you create a strong definition of your brand, attract more customers, and build a loyal audience who will buy from you again and again.

Marketing Made Easy

Get the WoRKBOOK


As a business coach, consultant, boutique marketing and branding studio owner, mentor, and motivational speaker with over 20 years of experience, I've worked with Fortune 500s, SMBs, and startups in cities like Houston, San Francisco, Los Angeles, Seattle, and London.

With my help, businesses deliver greater value to their customers and increase profits while becoming respected leaders in their industries. The lessons I've learned (and the wisdom they bring) have allowed me to give entrepreneurs like you the problem-solving skills needed to realize your business vision. I am committed to providing the guidance and support you need to achieve your business goals. 

Meet Jennifer Taormina,  Business Coach & Marketing Leader Committed to Your Success

Subscribe Today!

Subscribe to the Home Office Monthly Memo and gain access to a wealth of expert advice, practical solutions, and inspiring stories every month. Delve into proven strategies for goal-setting, habit-building, and taking meaningful action, all designed to boost your profits and enhance your work-life harmony. Don't miss out on your monthly dose of business insights and motivation – join me on this journey toward greater success and personal fulfillment..

Introducing the Home Office Monthly Memo: Unlock Your Business Growth and Success