How to Write a Winning Upwork Cover Letter (+Sample)

How to write an effective Upwork proposal cover letter

Crafting an Upwork cover letter that wins you the job is one of the two things that drive new Upworkers crazy (the other being how to get approved on Upwork).

That drove me crazy too when I started out. In fact, I must have spent 10+ hours and sent more than 20 proposals before I started getting replies.

I almost purchased a $300 course just to get access to their community’s Upwork proposal vault.

If you’re in a similar position, you have come to the right place.

In this article, let’s discuss how to write an effective Upwork proposal cover letter that will win you the job.

Let’s get this started!

From zero to hero

When I started using Upwork, it was a while until I was able to land a contract.

After I landed my first contract, I thought I had cracked the code and all I had to do was submit the same cover letter again and again.

Here’s what that (cringy and embarrassing) cover letter looks like:

Canned cover letter I used in the early days

(Good thing it happened before Upwork started banning accounts who submit way too many proposals without getting an offer.)

Using that stinky cover letter above, I still receive a few replies.

But that’s it — no new offers or whatsoever.

Two realizations hit me:

  1. I knew then that I didn’t crack the code.
  2. Canned, word for word cover letters don’t work.

After three years, here’s my marketing effectiveness:

The graph shows I was hired more often than my interview rate.

Stick until the end and I will show you an example of an Upwork cover letter I used to land a premium deal with a client.

Now, here’s how to make your cover letters better:

Answer the additional questions first

Many job postings will require you to answer additional questions besides submitting a cover letter.

Here’s a good example:

An Upwork job post with additional questions

As you can see, the cover letter comes first followed by the additional questions you have to answer.

Naturally, you may spend most of your energy trying to make that cover letter flawless and then, answer the additional questions with a one-line sentence only, like an afterthought.

What you may not know is that when the client reviews your proposal, he will see the additional questions first.

I discovered this when I posted a job on Upwork.

A sample Upwork job post looking for a writer

Here’s one of the answers I got:

An Upwork proposal with one-liner answers

Clearly, the guy didn’t get the job.

In a way, additional questions are more important than the cover letter itself.

Takeaway: When submitting a proposal for a job that has additional questions, focus on the additional questions and answer them comprehensively.

Address the client by name

Whether it’s an Upwork cover letter, a cold email, or a private message on Facebook, addressing the client by name has a great impact.

After all, names are the sweetest and most important sound in any language according to Dale Carnegie’s How to Win Friends and Influence People book.

But does it really increase the effectiveness of your Upwork proposal?

Well, calling the client by name is just the first part of making your cover letter more personal.

It shows him that you have done your research and most likely, the content of your cover letter isn’t canned.

As an example, let’s say that you’re the client and you need someone to write new articles on your website.

One of the proposals you received is this:

A canned cover without any personalization

Would you hire him? Exactly!

The question is, where will you get the name of the client?

How to find the client’s name

It’s easy enough when the job post has the client’s name.

Like this:

A job post with the client’s name

Unfortunately, only around 1 of 10 posts has the client’s name.

If this is the case, scroll down to the client’s recent history and find reviews from past contractors that mentioned the client’s name.

For example, this job post doesn’t contain any clue about who the client is.

An Upwork job post without the client’s name

But on the client’s recent history, you will find two mentions of his name there.

Finding the client’s name on his recent history

Sometimes, you may find different names on the client’s history. Some may address the client as Darren, Karen, or John.

To make matters easier, use the name mentioned in a review from a freelancer with similar services as you.

Let’s say that you’re a content writer. A past content writer left a review and addressed the client as John. In this case, use John in your cover letter.

Takeaway: Address the client by name to show that you have done your research and that you’re not using a canned cover letter. See the client’s recent history to find clues about the client’s name.

Show interest

By that, I don’t mean writing a line that says “I’m interested in your job post.”

There are usually two ways to do this:

  • Make a suggestion
  • Or ask a question

Let’s use this job post I found about a client looking for a content writer for his travel website:

A client looking for a content writer for his travel website.

Just because the job description was short, it doesn’t mean you have to put in the same effort and make your cover letter short.

This is often a mistake I see new freelancers do.

But how will you add value to a post as short as this?

If I were to submit a cover letter to do this job post, here’s what I would do:

  • Explain to the client what an excellent about us page is and what it contains. (If you’re not aware, the about us page, in addition to telling your story, is an excellent waypoint to different pages or content on your website.)
  • Include links to show him what I mean.
  • Suggest how I can do the same.
  • Ask him for a link to his website.

Takeaway: Clients love it when you show interest in helping them achieve their business goals. Do so by making a suggestion or asking a question.

The rate matters

This part isn’t much about the cover letter itself but on what job post you submit your cover letter to.

One of the things I have learned over the years is that there could be a mismatch between your rate and how much your client can afford or is willing to spend.

For example, no matter how good your cover letter is, it’s impossible for you to ask a high rate for this project.

A job post with a low rate

How did I know this? Looking at the client’s recent history, he paid someone a measly $25 for an educational blog.

Recent job history of a low rate project

From the client’s recent history, you can be certain that he’s only looking for freelancers with (super) low rates.

One more thing: Avoid low-ballers.

These clients will not pay you for what you’re worth. You will only be wasting six connects which you could have used to submit a proposal to a premium project.

Takeaway: Before you submit a proposal, check if your rate and the client’s budget match. No matter how good your cover letter is, it will only be a waste. Look for job posts that fit your rate.

Mention your experience

I have read numerous posts from “freelance gurus” that you don’t need experience to land premium contracts.

Although there’s truth to it, it’s not the whole truth.

As a client myself, I would like to make sure that the freelancer has the capability to do the tasks and that he’s willing to learn if he doesn’t have the skills yet.

However, freelancers who have previous similar experience and can prove it will most likely win the contract.

Why? Because it’s more certain that they will be able to do the job better and quicker, which is a win for clients who go into hourly contracts with freelancers.

In addition to experience, include samples of related work or outcome which you know the client would love.

For example, after including relevant samples of my work, this client has responded well to my cover letter and we ended up working together.

How the client responded to my samples in the cover letter

If you don’t have any relevant samples, just create one, and show it to the client.

Takeaway: The lesson here is to show, don’t tell. Experiences and samples will always weigh more than words alone.

Include one call to action

At the end of your cover letter, invite the client to do something. It’s proven that they will likely do something if you tell them exactly what to do.

It’s tempting to say “Hope to hear from you soon” or “Hoping for your kind consideration”. But it doesn’t really invite the client to do something.

Here are good examples of effective CTA (call to action):

  • Hit that reply button over there to continue our conversation. (Favorite)
  • How about we hop on a five-minute call to discuss your business needs?
  • If you want to collaborate, let’s discuss it more over the chat.

I have been working with different combinations and so far, the first one has worked best for me. However, I don’t think there’s much difference as long as you keep your call to action, clear, specific, and easy to commit to.

Takeaway: In your cover letter, include one call to action at the end. So far, I found “Hit that reply button over there to continue our conversation.” works best for me.

Keep a swipe file of Upwork cover letters

If you’re not familiar with what a swipe file is, it’s basically a folder where you keep all awesome ideas, copies, content, and ideas you have encountered.

In this case, keep a swipe file of Upwork cover letters that worked. Then, reverse engineer them and see why they work.

This is actually how I started improving my cover letter. I found and saved the winning cover letters I found online and try to understand why they worked.

I usually have three places where I store them:

  • OneNote (favorite)
  • Google drive
  • Local drive

A piece of advice: save your cover letters that worked.

Here’s mine:

A collection of my own Upwork cover letters that worked.

Since I have a record of what works and what doesn’t, I regularly update and optimize my cover letter to reflect what I recently learned.

That’s how I knew which call to action I thought worked best.

Takeaway: Save all Upwork cover letters you think are impressive. Create a collection of all your winning cover letters so you would know what works and why they worked.

Example of a winning Upwork cover letter

As promised, here is a cover letter I used to land a premium deal with a client.

Note that you can use the pattern I set but make sure you don’t use exact words. This cover letter was designed solely for the certain job post this cover letter was submitted to.

A cover letter I used to land a premium deal with a client.

In a gist, here’s how I did it:

Hey [name],

I’m sure you’ve got a lot of pitches to deal with so I’ll keep this short.

I help [your target industry] [the outcome your client would like to get from your service].

In the past, I helped [a previous client you worked with] [the outcome you helped your previous client achieved – should be similar to the outcome the client would like to get].

Here are links to some of my work:
– [link 1]
– [link 2]
– [link 3]

[Ask a question or suggest something]

Simply hit that “Reply” button over there so we could continue our conversation.

[Your name]

Feel free to use this template.

Win premium clients with a personalized cover letter

Writing a winning cover letter is easier than you think. But it will need a lot of practice and trial and error to finally get it right.

As I said, it took me so much time and proposals before I got a reply. From there, I continued optimizing it and see what works for my target clients and industry.

I’m definitely positive that as you practice and write more proposal cover letters, you will get better and win jobs.

And if you get lost, try the template I provided above.

Now it’s your turn. Here’s what to do now:

  • Go back to Upwork and apply what you have learned from this article.
  • Use the template and check my sample for inspiration.
  • Get back here and let us know how it went.

And as always, let me know your thoughts by sharing your comment down below.

About Alan

Alan helps different companies generate more qualified leads and increase their sales by educating their readers with strategic content and writing blogs. He's also the founder of Work Pajama.

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Genera V
Genera V
19 days ago

Hi Allan!

I am new and wanted to have virtual work ASAP. Thank you for this blog, will surely help me with my application. Wish me luck!

Stay safe always.


Genera V.