Upwork Proposal Tutorial for Beginners: The COMPLETE Upwork Cover Letter Guide (+ examples)

Sirarpi
4 min readApr 27, 2024

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Now that I am not only a freelancer but also a client on UpWork, I can see how those “Cover letter template tips” hurt you.

That’s why, we are talking about it. I want you to stop sending templated cover letters on UpWork. Save your energy, money and time.

Here’s what you should do instead.

I know this thumbnail is cringey for Medium. But works magic on YouTube.

Ok, we are avoiding templates.

What should we do instead?

Firstly, before we talk about what to do, let’s talk about some common mistakes we need to avoid when writing a cover letter on Upwork.

Mistake #1

Firstly, it’s essential to understand that not all jobs are right for you. Too many freelancers apply to jobs in a shotgun approach, hoping that the more they apply, the higher their chances of landing a job. But this is a flawed strategy.

Why, you ask?

Because every job is different, every client has unique needs, and every project requires a different skill set.

So, take the time to read the job description thoroughly.

Understand what the client needs and reflect on whether you have the necessary skills and the time to complete the job.

Mistake #2

The second mistake I see often is using the same cover letter for every job.

If you were a client, would you hire someone who sends you a copy-pasted, generic letter?

Or would you be more inclined to consider someone who has taken the time to personalize their cover letter, addressing your specific needs and expectations? I bet it’s the latter.

So, make it a point to personalize each cover letter.

Take cues from the job description and incorporate those phrases in your cover letter.

This will not only demonstrate that you’ve read the description carefully but also show your enthusiasm for the project.

Mistake #3

A mistake that is often overlooked by freelancers is not checking the client’s details.

Understanding the client’s location can provide insights into their time zone and whether your working hours align.

It’s also important to consider the hiring rate and the average amount they’ve paid to other freelancers.

This will give you an idea of their budget and whether it aligns with your rate.

Mistake #4

An extremely valuable but often neglected area is the feedback section.

This little goldmine can reveal critical information about your potential client.

You might even find the client’s name here — a key detail that can help you personalize your cover letter.

Additionally, reviewing the feedback can help you understand the client’s work history, how they interact with freelancers, and what you can expect when working with them.

Mistake #5

Finally, the skills section. If the job doesn’t match your skills, it might not be the right job for you.

This seems obvious, but you’d be surprised by how many people ignore this. Your skills should align with the job requirements.

This increases your chances of getting the job and also helps Upwork’s algorithm match you with similar jobs in the future.

Now that you know what to avoid, you are ready to know how to write a winning cover letter.

Photo by Ewan Robertson on Unsplash

HOW TO WRITE A WINNING COVER LETTER

Tip #1

Start by addressing the client by their name if you’ve managed to find it. It adds a personal touch and shows that you’ve taken the time to understand them. If not, a simple ‘Hi’ works. But make sure to keep it professional.

Tip #2

Your first sentence should grab the client’s attention. Address the most important aspect of the job post first.

For example, if the client has stated, ‘I want it done today’, you can start your cover letter by saying ‘I can deliver the work to you by today’.

This shows the client that you’ve read their requirement and you’re ready to meet their expectations.

Don’t waste your time writing long and boring introductions. It will do you no good.

Tip #3

You can also share relevant experiences and how your skills can bring value to the client and the project.

Make sure it’s short, to the point, and impactful.

Remember, less is more. Nobody wants to read a long cover letter.

Tip #4

Another good idea is to personalize wherever possible.

For example, unstead of saying “this project” say something from the job pots “company logo” or something else the client is looking for.

Tip #5

Finally, there is no need to end with a strong closing sentence.

And a pro tip — double-check your cover letter for spelling, grammar, or punctuation errors.

They can leave a bad impression.

As a takeaway, here are 2 different examples of cover letters that won the job in no time.

The examples are based on my videos as I asked my friend to test my advice of NOT using cover letter templates. Those are some of the results.

Here, you can see that the freelancer read the job description carefully and addressed the clients’ questions

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Sirarpi
Sirarpi

Written by Sirarpi

Digital marketing manager & freelancer with 6 years' experience. I share only proven advice on remote work and freelancing.

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