How to Write a Winning Upwork Cover Letter for Writing Jobs
By: Hannah Leigh
Tags: Freelancers, Upwork, Freelance Writing, Cover Letter

My first ‘digital nomad job’ was a freelancer writer. I applied for jobs on Upwork writing articles, books, product descriptions — just about anything you can imagine. And after several years of pitching clients and landing jobs, I perfected my cover letters. It sounds a little cocky, I know, to say I ‘perfected’ them but for the last two years that I worked through Upwork, every pitch I sent out resulted in me being hired.

So as my talent seems to lie in writing Upwork cover letters, I thought I’d write a post about it, for anyone else who wants to go freelance so that they travel while working. Plus, I no longer use Upwork, so I don’t mind sharing my secrets.

How to Write a Winning Upwork Cover Letter (for Writing Jobs)

If you want to succeed as an Upwork freelancer and land the higher-paying jobs, you’ll need to perfect your cover letter. There are thousands of freelancers out there, so whatever jobs you apply for, you can expect a fair amount of competition.

Cover letters are the first impression that potential clients are going to get of you, so you need to 1) sell yourself, and 2) stand out from the rest. Most of the time, clients don’t even bother looking at your profile, which is probably not what you want to hear if you’ve spent ages perfecting your profile (sorry). They skim your cover letter, check out your previous reviews and make a decision.

The only trouble is, if you’re new to the freelancing world, it can be hard to know exactly what clients are looking for and how to impress them. So here’s everything you need to know about writing job-winning cover letters.

Be Friendly and Conversational

Most clients are looking for writers who can write in a conversational style. They want to see that your friendly personality is going to shine through your writing. And the first piece of writing they’re going to see from you is your cover letter.

Don’t make the mistake of making your cover letter too formal. Generally freelance writing jobs are fairly casual, and clients want to skip past the normal formalities of hiring someone. Plus, if you can sell yourself in a conversational cover letter, you’re already proving that you can write in the style they’re looking for.

Check Your Cover Letter for Spelling and Grammar Mistakes

You’re applying for a writing job, so don’t let clients’ first impression of you be that your English writing skills aren’t quite up to scratch. Any proposals with spelling mistakes are probably going to be dismissed instantly.

How to Start Your Upwork Cover Letter

Knowing how to start a cover letter, and how to address the potential client is something that a lot of freelancers struggle with. The trouble with Upwork is that you don’t always have access to clients’ names. So how do you address them in your cover letter?

Every freelance writer has their own approach, but we’d suggest either a simple ‘Hi!’, ‘Hello!’ or if you want to be more formal, try ‘Dear Hiring Client’.

Using ‘Dear Hiring Client’ is a great way to let your potential clients know that you’re a professional, but at the same time, it’s a little distant and impersonal. When applying to any conventional job you’d definitely want to steer clear of starting your application with ‘hello’ but Upwork clients are looking for an informal working relationship. So if a simple ‘hello’ is more natural to your personality and style, then go for it.

Don’t Ramble: Keep Your Cover Letter Short and Sweet

If you’ve got quite a lot of writing experience, it’s easy to fall into the trap of rambling about all the different articles you’ve written. But your cover letter isn’t just for you to ramble on about how great you are (even if you are incredible). It needs to be more specific than that.

By all means mention your experience, but make it relevant. If you’re applying to write articles for a beauty or fashion blog, they probably don’t want to hear about your experience writing technology reviews.

Keep it short and sweet, this way your cover letter should be relevant, and won’t send the hiring client to sleep.

Be Honest: Lying or Exaggerating Your Abilities Will Lead to a Bad Review

More often than not, hiring clients are experts in their field, or at least, they know a lot. So if you don’t have all that much experience or knowledge of their field, be honest about it. If you pretend to be something you’re not just to get the job, they’ll soon realise, and that could result in a bad review.

So there’s no sense in lying in your cover letter. Even if you have no relevant experience, just be honest. As long as you seem keen to learn and get started, clients don’t always mind too much if you’re a little inexperienced.

Answer the Questions Clients Haven’t Asked Yet

Some clients ask specific questions that want you to answer in your proposal, but some clients don’t. And for these jobs, you should go above and beyond and answer the questions you know they’ll want answers to. This way, you’ll be showing that you’re organised, and that you’ve done this before.

So what questions does every hiring client want to know the answer to? Here are the staple questions that I always try and answer in my cover letter:

What relevant experience do I have?

What is my writing style like?

How long will it take me to complete the job?

What is my bid for this job?

Answer these questions, even if the hiring client hasn’t asked them yet. You’ll appear organised and professional. And if you’re applying for a job that involves writing longer pieces, maybe detail how you’d go about the project, how you’d structure it.

Don’t Use a Templated Cover Letter for Every Job

Hiring clients can spot generic cover letters from a mile away. And they hate them. You can tell straight away which cover letters have been copy and pasted, and which have been thought out in detail.

It might be easier to have a cover letter that you use to apply for every writing job, but you’re not going to land all that many jobs.

It’s fine to have a general template that you use, a structure to follow, but spending a couple of minutes making it personal is going to see much better results. Think about it, would you hire someone who hadn’t even made an effort to apply properly?

Attach or Include Links to Articles You’ve Written

If you provide potential clients with links to articles you’ve written, you’ll be making their life a whole lot easier, and they’ll thank you for it. No client wants to take the risk of hiring a writer without knowing what their style of writing is like. It’s just too much of a gamble.

So in your proposal, include a link or two, and you’ll massively increase your chances of being hired, especially if the clients are instantly sold on your writing style. If you don’t have any live articles you can link to, you can always attach Word documents to your proposal.

If you don’t have any writing examples yet, you really need to focus on building your writing portfolio. Start your own blog, even if it’s just a simple WordPress one, and write about something you’re passionate about. At least this way potential clients will be able to see your writing style at its best.

Or if you’d rather not start a blog, spend some time applying for and completing lower paid jobs. You may earn next to nothing, but you’ll have some experience under your belt.

So to Sum Up…

Writing cover letters doesn’t have to be difficult or stressful. You just have to know what hiring clients are looking for, and how to structure your proposal in a way that positions you as the answer to all of their problems.

Follow these tips, and you’ll start to find a cover letter style that works for you. Then the more cover letters you send off, the better you’ll get at writing them, and the more jobs you’ll start to land.