10 Simple Ways To Make Your Upwork Cover Letter Stand Out

Using Upwork can be a great way to do work that you love, on your own time, and from anywhere in the world. But getting started can be overwhelming. There’s a lot of competition for jobs, and you have to stand out.

You may have heard that the secret to getting hired is to write a kick-ass cover letter. And that’s true.

How to Write a Great Cover Letter (with Samples/Examples)
Writing an Upwork cover letter is crucial in winning proposals.
Tailor your cover letter to the specific needs of the client and highlight your relevant skills and experience.
Your Upwork cover letter should be concise, ideally between 100 to 200 words.
Demonstrate your enthusiasm for the project and include a call to action in your Upwork cover letter.
Focus on submitting high-quality proposals rather than quantity.

Table of Contents

My Experience

I’ve been freelancing full-time through Upwork for almost two years now, and I’ve worked on hundreds of projects with dozens of clients. Out of all those gigs, I think about 10% came from the submission of proposals (the vast majority came from repeat clients).

And I know what it’s like when you submit a proposal and then… radio silence. Or worse, when you accidentally mention something that makes you sound unprofessional or terrible at what you do.

Crafting a compelling Upwork cover letter is crucial for winning proposals. Don’t miss out on your dream job – read our guide on how to write a killer Upwork cover letter with real samples to land your next project.

What Is A Cover Letter

A cover letter is a short, but detailed introduction of yourself to potential employers. It is generally the first thing they will see from you, and you want to make sure it is user-friendly, concise and professional.

It should be written in a clear and friendly tone. Keep it simple, but informative. You don’t want to write a lot of unnecessary information or use confusing language that may make the reader stop reading your cover letter.

10 Things To Keep In Mind

Here are ten things to keep in mind when writing an Upwork cover letter that will help you land more jobs

1. Read The Entire Post Before You Start Writing

Don’t assume anything. Take nothing for granted. Even if it’s an hourly job and the client says only “I’m looking for a writer to write stuff,” read through the entire post carefully.

Before you start applying for jobs, it’s important that you read through each job post carefully. Clients will usually give specific instructions on what they want in their cover letter. Some clients might even provide a template for you to follow when creating your cover letter.

Example of Upwork Job Post

Upwork Job Sample

2. Identify What Skills They’re Looking

Upwork clients often have specific skills they’re looking for, but instead of calling it “skills,” they’ll use phrases like: “I’m looking for someone…” or “You must be able to…” or “Please include information about…” or “Please tell me about your experience with…”

Answering additional proposal questions on Upwork can be challenging, but it’s a critical step in winning new clients. Learn how to respond effectively by checking out our guide on how to answer additional 23 Upwork proposal questions today.

3. Make Sure Your Cover Letter Is Actually About Them, Not You

Remember: Your potential client doesn’t care about you. 

One way to ensure that your cover letter is responsive to the job opportunity is by using keywords from the job description in your cover letter. This will not only increase your chances of being selected for an interview.

4. Tailor Your Cover Letter To Each Job Posting

Never use a generic cover letter for all applications. While this might save time, it won’t get you anywhere. Each cover letter should be addressed to the client personally, with regards to the job title and description.

Upwork lets freelancers save cover letters so that they can be used again and again when bidding on jobs.

This is great – but don’t just use the same cover letter every time! It shows that you haven’t put any real effort into your proposal and most clients will notice this straight away.

Make sure that you customize each cover letter so that it fits with the job posting, even if it’s only small changes

 5. Write Simply And Clearly

Your client should be able to understand what you are saying in one reading of your proposal. If a client has to read through your proposal multiple times or decipher complicated sentences, they may simply move on to the next proposal instead.

6. Highlight A Unique Skill Or Experience That You Have

In order to demonstrate that you’re a good fit for the job, you need to show that you’ve done your research on both the company and the role. Be sure to show how your skills and experience match up with what they’re looking for in a candidate.

Be positive but never overconfident or arrogant about your skills and experience. You should be able to sell yourself without sounding like you are bragging about yourself or your skillsets.

Winning proposals on Upwork takes more than just luck – it requires a well-crafted cover letter and attention to detail. Get inspired by our top 5 winning proposals on Upwork and take your freelance career to the next level.

7. Personalize Your Greeting And Include A Thank-You Note At The End

Address the client by name. This is another way of showing that you actually took the time to read their project description, and will help you stand out from other proposals that are copied/pasted multiple times.

You can see the client’s name on Upwork by checking the client’s reviews. People who have worked with that client will surely mention the name in their review, so you’ll know exactly what it is.

Use bullet points to highlight 3-5 of your most relevant skills and accomplishments that match the job requirements. Bullet points are concise and help make it easy for clients to see why you are qualified for the job.

Creating a winning Upwork cover letter as a web developer requires a unique set of skills and experience. Check out our Upwork cover letter sample for web developer to get tips on how to tailor your cover letter to your next web development project.

9. Avoid Typos, Grammatical Mistakes And Other Errors

This should go without saying, but I’ve seen many applications with spelling mistakes in them. Always use spell-check before sending off an application – it only takes a few seconds but it can make such a big difference!

10. Research The Client And Their Business

Not all clients take the time to write detailed job descriptions and that’s not always a bad thing. But when they do, they’re giving you a lot of information about what they want — to use it! Read through everything they post carefully, including the About Us page on their website (if they have one).

You want to show the client that you’ve put thought into your application and that you’re not just sending out the same old generic message to everyone.

The most effective way to do this is by researching their business and explaining why you’re excited about working with them in particular.

The length of your Upwork cover letter can make a big difference in winning proposals. Find out how long your cover letter should be by reading our guide on how long should the Upwork cover letter be, and start writing proposals that stand out.

Final Thoughts

We have laid out an efficient and effective way to write a winning Upwork cover letter. The tips listed above should help you acquire the writing skills necessary to become a successful freelancer. Hopefully, you now feel more confident about the task at hand, and will be able to craft an amazing Upwork cover letter that will land you more jobs sooner!

Further Reading

Morgan Overholt: How to Write an Upwork Cover Letter (Samples Included): Check out this detailed guide with examples of winning Upwork cover letters and learn how to craft a cover letter that stands out.

eBiz Facts: How to Write a Killer Upwork Cover Letter (Tips & Examples): Find out how to write an Upwork cover letter that catches the attention of clients and increases your chances of winning proposals with this comprehensive guide.

Ink for All: Sample Cover Letter for Upwork Proposal: Get inspired by these sample cover letters for Upwork proposals and learn how to tailor your cover letter to your next project.


Q: How important is the Upwork cover letter?

A: The Upwork cover letter is critical in winning proposals as it’s the first impression you make on potential clients.

Q: What should I include in my Upwork cover letter?

A: Your Upwork cover letter should include an introduction, a brief summary of your skills and experience, your understanding of the client’s needs, and a call to action.

Q: How long should my Upwork cover letter be?

A: Your Upwork cover letter should be concise and to the point, ideally between 100 to 200 words.

Q: How can I make my Upwork cover letter stand out?

A: To make your Upwork cover letter stand out, tailor it to the client’s specific needs, highlight your relevant skills and experience, and demonstrate your enthusiasm for the project.

Q: How many proposals should I send on Upwork?

A: The number of proposals you should send on Upwork depends on your availability and the quality of the proposals you submit. Focus on submitting high-quality proposals rather than quantity.

Writing a Winning Upwork Cover Letter FAQs

Question: What is a cover letter?

Answer: Cover letters are where you can explain why you’re the right fit for the specific client and job. You can make sure your skills, experience, and personality shine through by using the same tone and style as your profile.

Question: How can I improve my cover letters?

Answer: Be direct: Clients may receive dozens of proposals, so yours needs to stand out quickly if it’s going to get noticed at all. If your profile has great feedback from previous clients, mention

Question: When hiring freelancers on Upwork, what are the most important things you look for in a cover letter?

Answer: What I look for varies depending on the job. For jobs that require technical skills, I want to see that the freelancer has done their research about the job and my company. If they can include a relevant example of their work and show that they’re up-to-date with the latest trends in our industry, all the better.

Question: What do you think are common mistakes freelance job seekers make when applying for jobs on Upwork?

Answer: Most people don’t take enough time with their cover letters or submit one at all. That tells me right away that the job seeker is either not serious about this particular opportunity or doesn’t care enough to invest time into it.

Question: How important is it to write a custom cover letter for each application?

Answer: Cover letters should be customized per project. It’s clear when someone has cut and pasted from a previous application because there are details that don’t.

Question: Do I need to write a cover letter if I apply for a job on Upwork?

Answer: Yes! Even if the client doesn’t request one, you should include a cover letter with every application.

Question: What should I put in my Upwork cover letter?

Answer: Include the following three elements in your cover letter:

Introduction – A brief description of who you are and why you’re applying (1-2 sentences)

Main Body – Tell the client why you’re the perfect candidate for the job (2-4 sentences)

Conclusion – Summarize your interest and qualifications and thank them for their time (1 sentence)

Question: How can I stand out from other freelancers?

Answer: Highlight your knowledge of the client’s a business and industry. Find opportunities to show that you understand what the client needs and explain how your past work has helped similar businesses. If possible, offer suggestions on how to achieve the client’s goal. This is your chance to stand out and show why you would be an asset.

Question. What’s the best way to start my cover letter?

Answer: In most cases, starting your cover letter with “Dear ” works best when addressing clients by name. It’s also okay to begin your cover letter with “Hi,” or “Hello,” if you prefer.

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