Hiring on Upwork and the Significance of a Cover Letter

I wrote a previous article about the importance of cover letters directed towards freelancers and those applying for positions on Upwork. 

However, I believe its equally important to cover the importance of cover letters from the perspective of an employer/hiring party as well.

A quick way to do the first round of filtering

If you’re posting a job where the applicant pool is likely to reach past 50 (e.g., graphic design, web design, virtual admin, social media, project management, etc…), then you need a way to quickly filter out applicants. 

Of course, you may think the first way is to look at the Job Success percentage. However, that rate can be misleading and can be dragged down by various factors, including if they’ve had a job posting open too long without any sort of activity. 

So, move on to the cover letter first. 

For me, as an employer, a properly written cover letter should be able to explicitly/implicitly tell me:

  • They’ve read the full job posting and have researched my company if possible.

  • They’ve written the cover letter with original content, rather than Copy+Paste.

  • That they’re actually interested in the work they are applying for by directly addressing any pain points / problem areas identified in the posting.

  • That they’re confident.

Cover letters that make me press “Archive” right away

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One liners:

  • “Thank you for inviting me, looking forward to working with you”

  • “Let’s talk”

  • - - - (yup, a couple of dashes to meet the cover letter requirement and submit a proposal… it’s happened)

When I’ve actually invited them and they have my name and company:

  • “Dear Sir/Madam”

  • “To whom it may concern”


  • When it’s clear they have one cover letter for every job posting

  • When the cover letter doesn’t answer anything I’ve asked for

  • When the cover letter is so long, but doesn’t have anything to do with the job posting

What a good cover letter can substitute

For freelancers new on Upwork, it’s really hard to break the seal of being completely new and having absolutely no work experience on the platform. 

I know that many people hiring may automatically decline those without any experience, but take a second to think about the fact that they could have been freelancers outside of Upwork and probably have a breadth of experience that you’re not even considering. 

Especially for these folks, when I see a “good” cover letter come from them, it tells me that they’re ambitious and eager to get their foot in the door, and that they’ve not given up and resorted to mass applying with templated cover letters. 

Give these folks a shot, and have a conversation. You’ll be surprised at the talent you have to choose from and will wonder what other great gems you may have canned right away.

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Closing thoughts

A lot of people hiring on Upwork are not large corporations or in an HR-specific role. If you’re like me, you’re a company owner that is wearing a few hats, and I’ll tell you that the recruiting hat is not one that I find all that enjoyable to wear.

These are all things that I’ve learned over the last 4 years recruiting talent from Upwork, all tips from the mistakes I’ve made and the good talent I’ve accidentally passed over. 

What else do you think makes a cover letter good? Any other tips for the rest of us on how you’ve recruited more efficiently on these freelancer sites like Upwork? Let us know in the comment section below!