My Top 5 Winning Proposals On Upwork And The Earnings I Made For Each One

Upwork is one of the most popular freelancing platforms that connect clients with freelancers. It gives you an opportunity to work from anywhere in the world. But it’s not easy to get a job on Upwork. You need to be creative, smart, and persistent to get a job interview and win a project.

It’s a big world out there in Upwork. And it’s a crowded one

When you are bidding for projects on this platform, your proposal is everything that separates you from the competition.

TOP 5 Upwork Proposal Tips from an $847243 Freelancer
Crafting an effective proposal on Upwork requires personalizing it to the specific project and client.
Providing clear and concise explanations of how you can help the client with their project is crucial.
Highlighting your relevant experience and skills can make your proposal stand out.
Including samples of past work that demonstrate your abilities can help clients make a decision.
Following up on an Upwork proposal after a few days can show your interest and professionalism.

UpWork Cover Letter Mistakes 

And yet, so many freelancers make the mistake of copy-pasting the same proposal over and over again to every job posting they see. If you are desperately looking for jobs on Upwork, but have little to no success there, then you are probably making one or more of these common mistakes:

You don’t bother to write your own proposal; You use a generic proposal that looks like everyone else’s; You fail to tailor your proposal to a particular job posting; You fail to demonstrate how well you can solve the problem of your potential client; Your grammar sucks and your spelling is atrocious.

There are several other possible reasons why your proposals do not get any interview requests. But this post is about something else — about how you can create winning Upwork proposals that get interviews and clients.

The most important part of your success on Upwork is your proposal: how you write it, what you include in it and how you make it look nice.

If you want to succeed as a freelancer, it’s crucial to learn how to write an effective cover letter. Take a look at our real-life samples for writing a killer Upwork cover letter and improve your chances of landing the job of your dreams.

Real Upwork Cover

These are my 5 really good samples of Upwork proposals that won jobs and made money for their writers.

Theme: Transcription

Earned: $6,000 

Hi there! Iam excited to see you are looking for a Project Manager to recruit freelancers for recruiting at least 100 freelancers who have a standard native accent, training freelancers to be qualified data collectors and check the status of the collection, and coordinating the team to act accordingly.

I am a Swahili native speaker from Tanzania and I am capable to recruit more than 100 Tanzania freelancers with standard native accents to complete your project.

I am looking forward to having an interview with you to discuss more your project.

Best regards,


Extra Questions 

Would you prefer to work as PM (Project Management)to recruit freelancers or only work as a freelancer?

I would prefer to work as Project Manager

How many freelancers could you recruit?

I can recruit up to 200 freelancers

What is your expected salary for each qualified freelancer? (Successfully record 1000 sentences with a qualified rate of more than 95%)

I can work for a $15 salary for each qualified freelancer and the expected $3 commission as project manager.

Theme: Blog Writer

Earned: $3,680 – Ongoing (Full-Time)

 Hi Ramon,

I am ready to do the task of reviewing and writing SEO-friendly blog posts for and other related tasks that inspire and educate small business owners to start and grow successful businesses.

I’m a detail-driven writer who turns ideas into valuable blog content. I enjoy writing for various topics including business, lifestyle, travel, and personal blogs. My experience has given me a deep understanding of SEO writing and strong digital marketing strategies to help grab readers’ attention and drive traffic to your posts.

My current turnaround time for 1000-word articles is two days. If my work aligns with what you need, can we set up a time to discuss your goals for this project?

I have attached a sample of my recent blog posts.

Best regards,


Extra Question

Are you familiar with small businesses?

Yes, I am very familiar with small businesses and in fact, I’m running a small business that uses black soldier flies to turn food waste into alternative feed proteins. Here it is

What does being a content manager mean to you?

As a content manager, my responsibility is to oversee the creation and distribution of marketing content like blog posts, email, and social media pages. This role usually involves knowledge of tools, software, and methods to help execute my job functions.

What part of this project most appeals to you?

I would love to be a part of writing SEO content that can drive traffic to your website. If you are thinking about creating content for your website, I am the one you should be looking for!

Do you have suggestions to make this project run successfully?

I will be assisting you in developing a process flow for, your project requires SEO content because it can increase your brand awareness in the long run as well as drive traffic to your site to improve leads as well as revenue.

What past project or job have you had that is most like this one and why?

Ever since I have started working for AgriLife I have learned and experienced how the existence of social media affects SEO content from a business perspective. I am currently responsible for the online marketing for my business and I do it because I believe through online marketing and SEO content I can easily generate leads for my business.

Becoming a freelance web developer can be a daunting task, but with the right guidance, it’s achievable. Our step-by-step guide can help you start your journey towards freelancing and financial independence.

Theme: IGame Writer 

Earned: $412 – On Going (Full-Time)

I’ve never written about gambling before, I’m happy to add this to my portfolio.

Hi Barbaros!

I’m well-versed in English and have a background in writing, editing, and marketing. I would be interested in becoming a contributor to your website as I could help you write unique English iGaming content.

Let’s work together! I would love the opportunity to write engaging English content for your website. I can help you write fresh content geared towards your audience, so you can keep your visitors entertained and informed.

My work can be found on where I have been a contributor for the past months.

My rate for 1K words is $40 and my turnaround for 1000 words is 2 days.

I hope my work aligns with what you need, let’s set up a time to discuss your goals for this project?



Theme: Blog Writer 

Earned:$1600 – Ongoing 

Dear Stefan,

I am excited and ready to help you with writing SEO articles of web forms such as lead generation forms, business forms, registration forms that will increase your online rank and visibility.

I’m a detail-driven writer who turns ideas into valuable website content. I enjoy writing for various topics including business, lifestyle, travel, and personal blogs. You can find examples of my past writing work at and

My experience has given me a deep understanding of SEO writing and strong digital marketing strategies to help drive traffic to your web forms. I excel in writing all types of content such as blogs, press releases, product descriptions, and more.

I would prefer the fixed price.

Best regards,


Working with a freelance web developer can be a great way to grow your business, but it’s important to know when it’s time to move on. Learn about the 8 signs that it may be time to find a new developer for your project.

Theme: Land Page And Blog

Earned: $1,004 – Ongoing 

Hi Polina,

Yes, I understand that you need an SEO article writer who can create unique and 100% plagiarism-free human-readable content for your site. Likewise, one who can effectively follow the guide directions in producing the formatted article by employing all of the keywords supplied.

I am a friendly SEO writer with 2 years of experience in writing engaging, informative and properly formatted content for people and search engines. I work hard to make sure you are 100% satisfied.

I am really keen to discuss with you in-depth about your platform and find out more information about App Builder.



Tips To Craft A winning Cover Letter 

When applying for jobs on the gig economy platform, writing a cover letter is often more important than creating a resume.

Cover letters are not only important in applications for freelance clients, but they are also important in other fields of work.

If you have been applying to jobs on Upwork and haven’t been getting any responses, then it is time to step up your game. Here are ten tips on how to craft a winning cover letter:

1. Address the client by name

This will let the client know that you took some time to learn about them and their company. It also helps reduce your chances of sounding like a template or form letter.

Including a client’s name in the first line shows that you took the time to personalize your cover letter. This is important because it shows that you care about their project, which will help them gain confidence in hiring you. Also, by mentioning their name or company, they will know that you’re not just sending out generic proposals to everyone.

Starting a freelance graphic design business is an exciting venture, but it’s important to have a plan in place. Our guide on how to launch a freelance graphic design business outlines 15 essential steps to help you get started.

2. Read the Job Posting Carefully

The first step to writing an effective cover letter is to read the job posting carefully. You need to understand what skills are required for the job, how much time will be required, and how much money is being offered for it. You can then formulate your cover letter according to these requirements.

3. Do not copy-paste your previous cover letters

Do not send a template or generic cover letter to multiple clients and expect to get hired. Each client has different needs; therefore, each one deserves a personalized cover letter.

4. Keep it short (less than 300 words)

Try to keep your cover letter short and direct to the point. If it is too long, clients lose interest in reading it at all. Try to fit everything in less than 300 words so that they can easily scan all

5. Use Keywords

Using keywords from the original job post helps UpWork match freelancers with appropriate jobs based on skills and availability. If a job post mentions social media marketing then use that phrase

6. Demonstrate why you’re qualified for the position

Your cover letter should showcase your past experience and provide concrete examples of work that relates to what the client is seeking. If this is your first time working with Upwork, be sure to share why you think you’d make a great freelancer for this particular project.

7. Include Relevant Links

While research is important, don’t just tell the client about your experience — show them! Include links (or attach files) of past work that is relevant to the job listing so that they can see samples of your work.

8. Proofread before sending

It seems obvious, but many freelancers still submit a proposal with common grammar mistakes or typos. Your Upwork profile contains information about your education and experience, so you want to show that you can write correctly. Always proofread your cover letter.

Freelancing as a web developer can be a rewarding career, but it’s not without its challenges. Our article on 9 lessons learned from a freelance web developer provides valuable insights and tips for navigating the ups and downs of freelancing.

Final Thoughts

Finally, Make sure your cover letter is clear, concise, and relevant to the job you’re applying for. Mention previous work experience, refer the client to your portfolio, and make a good impression by ending on a positive note. Follow these tips and you too can write winning Upwork cover letters. We wish you the best of luck in landing on a client that’s just right for you and your business.

Further Reading

How to Write a Proposal on Upwork That Actually Gets You Hired: A comprehensive guide on crafting an effective proposal on Upwork that stands out from the competition and wins clients.

Upwork Proposal Rules You Need to Know to Win More Jobs: A useful resource outlining the most important rules to follow when writing proposals on Upwork to increase your chances of winning more jobs.

10 Upwork Proposal Tips To Win You More Jobs: A list of actionable tips to help you improve your Upwork proposals and stand out to potential clients.


What should I include in an Upwork proposal?

Your Upwork proposal should include a brief introduction, a clear explanation of how you can help the client with their project, relevant experience or past work examples, and a clear call-to-action.

How can I make my Upwork proposal stand out?

To make your Upwork proposal stand out, personalize it to the specific project and client, highlight your relevant experience and skills, provide clear and concise explanations, and include samples of past work that demonstrate your abilities.

How long should my Upwork proposal be?

Your Upwork proposal should be long enough to convey your relevant skills and experience, but not so long that it becomes overwhelming or difficult to read. Aim for around 200-300 words.

How many proposals should I send on Upwork?

There is no set number of proposals you should send on Upwork, but it’s generally recommended to apply to projects that are a good fit for your skills and experience, and to focus on quality over quantity.

When should I follow up on an Upwork proposal?

It’s a good idea to follow up on an Upwork proposal after a few days if you haven’t heard back from the client. You can send a polite message asking if they have any questions or if there’s anything else you can provide to help them make a decision.

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