3 tips for hiring a great copywriter

You’re neck deep in writing. You’ve never written so much in your life. Or you SHOULD be writing – but the days go by, and it’s just not getting done. You watch your “this needs to get written list” sit there. It doesn’t get shorter.

You tried to get your VA to do it.

It didn’t go so well. She’s great. Don’t get me wrong. That’s just not her wheelhouse.

So, you want to hire a copywriter. Smart thinking. Here at Stella Orange, we’ve got a stable of smart writers, crafting copy that wins friends and buyers. And I personally oversee every draft, giving a round of revision notes to my writing team BEFORE our clients even see it.

Lately, I’ve been talking with several of my colleagues and friends about what to look for in a quality copywriter. I’ve also found myself having a similar conversation with my clients who are copywriter. So I thought it would be helpful to share this with you, too.

1)   Start with a smaller investment. Pick a smaller project that you can “test out” the sales skills, work ethic, and fit of a copywriter. For a first time client, I like to keep proposals around $1,000.

This way, you can explore how well you work together — and you stand a better chance of making a return on your investment.

We were recently hired to write a simple 3 email campaign by a coach who had an already-successful group coaching program that she’d never tried selling to her list before. She made back more than 7 times what she invested in copywriting.

Now, that doesn’t happen all the time… sometimes campaigns don’t work, and limiting your investment also limits your risk.

2)   Use the asshole tax to your advantage. When I worked in an Italian bakery in Seattle, we occasionally charged people who were grumpy more. Life works like this, too.

As a copywriter, when I put together a proposal, I factor in how easy I think you’ll be to work with. I am willing to be more flexible on payment plans and extras — sometimes even price — when I sense that a client is a great partner and collaborator.

With that in mind, if you aren’t (ahem) eligible for this tax, you have some leeway. We regularly throw in extra writing work or phone consults for our clients, just to let them know that we think they’re nifty.

3)   Screen for thinking partners. When I get on the phone with a potential client, I am listening for the ripest opportunity that copywriting can harvest. If I don’t think I can make a client money on a certain project, I’ll tell them on the spot.

I’ve been told that not all copywriters work like this. They operate more like secretaries, and less like strategists.

But as a business owner myself, I can’t in good faith submit a proposal for a project that I don’t think will make money.

A few years ago, I had a client who wanted me to write a series of emails to promote a high level mastermind that cost more than a lot of people pay for their cars.

I told her I didn’t think it would work – she didn’t have a live event on the horizon. And she was trying to upsell people from a program that was less than $500. I suggested we focus on a project that stood a better chance of making her money.

I don’t believe in writing copy for writing’s sake. I believe in projects and campaigns that make money.

That said, you may have your strategy nailed, so this is less important. In that case, you just want to make sure you have a writer who “gets” you, and knows how to language your work in a way that is fresh and uncommon.

So there you have it – 3 tips to hiring a copywriter. Above all, I suggest looking for return on investment. I know that writing a newsletter and blog can be a pinch point for many business owners, but look for a project that is revenue-generating. What established offering could you promote with a simple 3 email sequence – that is ripe to bring to your mailing list? That’s often a great place to start.

Mighty thanks to sunshinecity flickr photostream for the ongoing list. To talk with Stella about Stella Orange writing copy for you, click here to set up a Project Consult.

What’s your experience been with copywriters? Share it the comments below.

Stella Orange is a copywriter who helps people put their work into words. For eight years, she wrote email campaigns that resulted in more than a million dollars in sales for her clients. In that time, Stella also taught popular marketing writing workshops to business owners on both sides of the Atlantic -- and a few in Australia and New Zealand. In 2017, Stella cofounded a creative and consulting shop offering a complete and slightly unorthodox line of business advising and marketing services. She continues to write copy and advise clients on customer delight, how to resonate with more sophisticated, discerning clientele in your marketing, and just who, exactly, your ideal clients are. Stella is the founder of Show Up And Write, a weekly writing group and writes a letter every two weeks or so (here’s the sign-up). She lives with the Philosopher and their two kiddos in Buffalo, New York, a fifteen-minute bike ride to the Canadian border.

4 Comments


  1. Lisa Manyon

    Brilliant as usual. I think the @$$hole tax is quite similar to the 100% markup for rush fees. 🙂

  2. Cathy Goodwin

    I definitely use the a**hole factor whether I’m working with a strategy client or a copywriting client. If I think you’re going to call me 5 times a day to ask, “Where’s my copy?” you’ll get a higher quote (and I may refer you to someone else altogether).

    I also agree to start small and see how you work together. If you’re nervous about hiring your copywriter and you ask a zillion questions, you won’t be a great client. Sadly you’ll end up with a copywriter who’s desperate and you’ll conclude that copywriters are worthless.

  3. Stella

    Lisa,

    I remember studying your stuff years ago, and noting that you did that. I love how you take a stand for how you intend to work, and yah, sure, we can hustle, but that’s a premium.

  4. online copywriting

    These are great tips and I would like to say that freelance copywriters as well as directors, editors etc. need help getting started. Marketing departments must answer two killer questions before looking to the creative industries to describe the solution.

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