A Guide to Writing a Winning Proposal On Upwork!

The proposal is one of the most critical parts of the freelance job process. The good news is that it's very easy to write a winning proposal—and the bad news is that you need to write it well.

In this post, I'll share with you everything you need to know about writing a proposal and how to ensure that you'll get noticed by the client.

Writing a Winning Proposal on Upwork

Your proposal serves as an introduction to you, your services, and your work. In other words, it's the first step toward showing prospective clients what you can do for them. It's a tool to let potential clients know you are the solution to their problems. 

In your Upwork proposal, don't try to get the client to hire you; capture their attention and get them to invite you to talk about the project. If you get an invite from a client, your proposal does what it's supposed to do. 

Characteristics of a poorly written proposal

Before I talk about a good proposal's characteristics, let me tell you the elements that make up a lousy proposal:

  • The proposal is too long for a quick read.
  • Has grammar, punctuation, and capitalization errors. 
  • No clear structure. 
  • No selling or marketing points.
  • No clear benefit to the client.
  • It is unclear what you will deliver.
  • Weak or no clear call to action at the end

While some clients read your proposals from start to finish, a vast majority skim through them, looking for one that stands out. 

So, how do you write a winning proposal?

A well-written proposal should be informative and engaging yet concise enough to convey the benefits of your service.

I will show you some cover letter samples, but first, let's talk about what you should include in your proposal.

1. A friendly greeting

Most freelancers overextend the friendly greeting by making it too long. A simple Hey, Hi, or Hello will do. 

2. Include the name of the client. 

If available, personalize your proposal by including the name of the client. You can find their name in the review section of their profile. Some freelancers would include the client's name when they leave a review (e.g., Anita is great to work with. I would love to work with her again.)

3. Tell them you've read the details of the job ad. 

A simple "I've read the details on the job ad and..." will suffice; this will allow you to highlight the points in the job ad. It shows you've done your homework and lets the clients know you've taken the time to read their ad and understand the job requirement. 

Alternatively, you can also say "I see that you're looking for a ____________ for your __________, I'm glad I found your job ad because I am _______________."

4. Tell them why you are the best fit for this job. 

This is the part where you talk about yourself. However, you have to have a structure here. Simply listing your skills, competencies, expertise, and experience is not enough.

Don't just leave the client to link 2 and 2 together; help them to pick you by relating your skills and experiences to what they are looking for. Essentially, you are telling the client that you are the most qualified of all the freelancers who submitted a proposal because of the skills and competencies you possess.

5. Call to Action

Most people like to be told what to do next, which makes a call to action very powerful. By prompting your client to take action, you help them decide what needs to be done, you reduce the chances of them moving away from your profile, and it can help convince clients to invite you for a meeting. 

There are many types of calls to action. However, the most successful CTAs are the ones that generate enthusiasm, emotion, or curiosity. So, saying "I hope to hear from you today" is bland compared to  "Let me help you with your business problem today!"

You can say:

  • Send me your questions to discuss the project with me today. 
  • Let's schedule a consultation or meeting today!
  • Message me now to discuss the details of the project and budget. 
  • If you have questions, send me a message today. 
  • I look forward to speaking with you today. 

I'm sure you've noticed that you are telling your client when to contact you besides the call to action—adding the words "now" or "today" gives a sense of urgency and persuades them to act immediately. 

6. Add a postscript

Most clients will skip the contents of your letter, but they are most likely to read the contents of your postscript or PS. I learned this technique from Lex Deville on Youtube

The postscript is a part of your proposal body found at the end; this is where you mention something extra about yourself, your proposal, or your skills. You can add many things here, such as links to your portfolio, your other proposals or case studies, or a testimonial about yourself.

You can add something like "PS Please keep my profile handy in case you need my services."

Here are some samples of an Upwork Cover Letter or proposal. 

WARNING: Copy-pasting anything is a mortal sin on Upwork and could get you banned. If you want to copy the below samples, COPY the IDEA, NOT the WORDS. 

Sample 1:

Hi Genevieve. 

I see you're looking for a virtual assistant who specializes in customer service and has a background in email support. You can stop looking now because you have already found one. 

I am Gino, a tenured virtual assistant veteran of the business process outsourcing industry.  I have over ten years of experience working as a Virtual Assistant, Client Support Specialist, Project Manager, and Customer Service Specialist.

As an experienced professional in Customer Service and Business Process Outsourcing, I understand the pain points and challenges you face in your business and have developed a clear strategy to help you succeed in your online business. I can provide excellent quality work that will exceed your expectations, bring value to your business, and make your life easier. 

I can start right away. Let's talk today and get things started!

PS I know your rate is 12 USD an hour, but I'm willing to start at 8 USD, and we can increase it back to 12 USD after a test run.



Sample 2:

Hello Hiring Manager. 

After reading your job advertisement on Upwork, I am convinced I can be your data entry specialist. Considering my extensive experience in typing, data processing, customer service, and my work-from-home setup, I believe I am the freelancer you seek. 

You can expect to receive high-quality work, punctuality, and accuracy if you hire me. In return, I expect you to pay me a fair and reasonable rate for my services.

Book a video call with me today to discuss the project. I am available to start immediately. 

PS I have a proven workflow that ensures 100% data accuracy. I can discuss this with you during our meeting. 

Best Regards,


Sample 3

Regarding social media marketing, most people are pretty poor at video editing and, even worse, at making videos. This can be frustrating, time-consuming, and expensive, especially if you're trying to build a brand. 

Hi, Michael. My name is Gino. I am a video editor extraordinaire. I specialize in creating fun, engaging, and original videos that help businesses tell their story, and I have been doing this job for nearly five years. 

Hiring my services means you no longer need to worry about these issues. I'll take care of the project's technical aspects so you can focus on your business. So what do I do?

I create professional, polished, creative videos from beginning to end. I work closely with you throughout the process and produce a high-quality final product. I ensure everything is properly optimized to rank high in search engines and ensure your message is received.

Here are some examples of projects I've completed over the years:

(insert portfolio link)

I'd love to hear more about your company and get started! Shall we discuss the details of your project today? Send me a message. 

PS: I just mastered a new editing technique that you might find beneficial for one of your programs. 


Sample No 4

Hi Jennifer. Today, I read your job ad about your struggle to find a social media manager. I couldn't stop myself from sending you a message because I'll admit, you were describing me with the details you added for the kind of social media manager you are looking for.

I am Gino, and I work as a full-time social media manager for various clients in different industries, whether their social media plan is new or existing. This is why you will benefit from my experience, as I know exactly how to deal with these issues.

In addition, I have experience with a range of other social media platforms, including Instagram, LinkedIn, Facebook, Twitter, etc. This would be an excellent fit for your business. I have several sample social media plans I could send you so you can see what I can do for you. You can check them out here (insert link). 

Do you have some time this afternoon? I want to talk about your social media efforts and see how I can best be of service to you and your business. 

Thanks, Jennifer. 

PS: I saw one of your company's posts on Facebook, and I can help you optimize that campaign for better engagement. 


Sample No 5

Hi James. I noticed that you posted this job ad three days ago. Still can't find a suitable content writer? 

My name is Gino. I've been a writer since the early 2000s. I've written content for dozens of clients all over the world. If you want quality blogs for your new website, look no further.

I have a unique social media marketing, blogging, and copywriting background. I've published dozens of articles on topics like SEO, web design, marketing, and content strategy. I also have extensive experience working with Fortune 500 companies. So if you're looking for someone who understands how to write content that will get results, I'm your guy.

Let's talk if you'd like me to look at your current content or maybe do a test run on some new material. I'm available for a video call anytime today. 

PS: If you have time, you can visit my blog to view samples of my work. Here is the link. 


Final Words

Writing a proposal or cover letter isn't that hard, but taking the time to do it right is crucial.

The real challenge is writing the one that converts.

Even if you believe your cover letter is the best cover letter of all time, many factors may affect your chances of getting the project.

The secret here is to keep trying, experimenting with your approach, and improving how you write your cover letters.

I hope you learned something from this article. What do you think is the most effective Upwork cover letter? Please feel free to leave your comment below.



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