Becoming a Freelancer - Advice on Upwork Cover Letters

In this post, I’m going to go over the importance and significance of cover letters when applying to jobs on Upwork. Not only about having them, but in general what sort of effort you should be putting into them. 

I speak from having both freelancer and employer experience on Upwork and will break it down for you. To start, I’ll cover some tips for freelancers. 

For Freelancers

Are you new to Upwork, have you applied to 40+ job postings without having even a single interview?

The cover letter, whether you’re new or a seasoned Upworker, I would argue, is the most important piece of your application.

A large majority of companies hiring on Upwork are either small businesses or solopreneurs (with no such thing as a formal HR department or even a recruiter). Most business owners are wearing the HR hat, too, and most find it daunting. 


Okay, I got that out. Let’s move on…

Making Up for a Lack of Upwork History

If you have little or no prior Upwork history at all, the cover letter is extra important. 

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Here’s what you should cover right away:

  • A brief summary of why you are becoming a freelancer and where you are coming from.

  • If you have prior experience as a freelancer, be sure to include links to where they can see others’ reviews of your work.

  • Don’t get too detailed or fluff up your cover letter.

  • Include a simple call to action along the lines of, “I’m invested in seeing if we’re both a good fit to work with each other, so let’s schedule a time to talk and figure that out. When are a few dates and times that work for you to have a quick call?”

Show that You’ve Paid Attention

Remember rules 1-100? If you copy & paste and don’t read the full job description, you may have missed something that they are specifically looking for in the cover letter. 

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Some common scenarios:

  • The job poster will bury a random fact in the posting and then will ask you to include it at the top of your cover letter.

    • e.g., “My favorite color is blue. Make sure to begin your cover letter with BLUE.”

  • They may ask for a specific link to a particular type of previous work that you can miss.

If a posting has a tone of confusion or uncertainty from the poster, then you’ll want to make sure to take note of all of their concerns and address them in your cover letter.

Show That You’re Actually Interested

Oh, did you forget rules 1-100? I hope not. 

As a job poster, I will hit DECLINE at the first sight of anything that looks like a recycled cover letter with no more than the greeting tailored. 

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Some great ways to show you’re NOT interested:

  • When you’re invited to apply directly and your cover letter is something short like - “Thank you! I look forward to working with you!” -- This will most likely get your application ignored or rejected within seconds (unless you have a wildly in demand and probably somewhat rare technical skillset). 

  • “Dear Sir/Madam” “To whom it may concern” - 🤢 Okay, maybe this is another hiring quirk of mine, but I’ve seen this even after I directly invite someone to apply, which means they have my name in the invitation. This is such a clear 🚩that it’s a template.

  • “Let’s Chat” - this is a one line cover letter I’ve gotten. Hmm… let’s say we don’t? 

Okay, by now you should get the point...

First Impression

Your cover letter is the first impression that you are putting in front of a potential client. If you show a lack of attention to detail, a lack of interest, or come off unmemorable, what makes you think that you’re going to make it onto the shortlist and on to an interview?

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Sometimes job posters will get 50+ applicants, and if they are the owner wearing the HR hat, they’re bound to be overwhelmed.

What they’re going to do is take a swipe through and “archive” responses that:

  1. Have no experience and a lacking cover letter (or no cover letter)

  2. Have experience and a lacking cover letter (or no cover letter)

  3. Have a clearly templated and/or irrelevant cover letter to start

If you’re reading this article, I know you are tired of not hearing back from your applications. Perhaps you did put the effort into the first handful of cover letters you submitted but then got discouraged and began down the templated route. 

Keep writing custom cover letters; Your efforts will be noticed. Sometimes, I interview and even have hired applicants solely based on their cover letter -- often, if compelling enough, I won’t even feel it’s necessary to read too deeply into their resume or prior work experience.

So, put some time into your cover letter.

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