Within a year of starting on Upwork, I successfully earned over USD$30K and achieved Top-Rated Plus freelancer status. I honestly believe that my cover letter played a significant role in this accomplishment.
The importance of a well-crafted cover letter cannot be overstated; it is a crucial factor in securing the jobs for which you apply. I have been selected for positions that attracted over 30 other applicants, which reinforces my confidence in the effectiveness of my approach.
After writing well over 100 cover letters on Upwork, I have learned a few key lessons by experimenting with different styles. In this blog, I would like to share 3 tips on how you can create the most effective version of a winning Upwork cover letter, along with some samples, regardless of the type of work you do.
Tip #1 on Upwork Cover Letter: Customize for Each Client By Addressing Their Needs
If you were expecting a one-size-fits-all Upwork cover letter template that magically works for every project, I’m sorry to say that it doesn’t exist. In fact, if you’re using such a template, I suggest you throw it out the window IMMEDIATELY.
As you know, there are many different types of jobs with a wide range of budgets, project lengths, and skill levels. Adjusting the style of your cover letter to align with your client’s expectations is a highly effective way to increase your chances of being selected for the project.
Let me elaborate with a few examples.
Example 1: Low-Budget, Urgent, Quick-and-Easy Projects
This would be a typical job that a beginner like yourself should apply for to build your reputation and earn 5-star ratings on Upwork.
If a job posting includes the word “URGENT” and is a one-off small project for a fixed price of $20, the client is likely looking for a relatively simple task to be completed ASAP, probably on the same day by someone who appears trustworthy and possesses the necessary skills.
In this case, you shouldn’t write a lengthy cover letter. The client is in a rush and VERY likely won’t read it if you do—let alone take the time to read your profile page (Would you spend time reading a long cover letter for an easy $20 job?).
The important key here is to address the client’s needs directly like this:
Hi, I am available to start immediately and can complete the task within one hour of receiving the official job offer. My skills and experience, as demonstrated in my portfolio, make me well-suited for this position. I will be online for the next 4 hours to ensure a prompt response when you reach out to me.
Thank you
<Your Name>
Yes, that’s it—short and sweet in just 3 sentences. This urgent type of job posting suggests that the client wants to know whether you can start right away when you can complete the task, if you have the skills to do the job, and whether you will be available when they reply to you (It’s frustrating for clients when freelancers don’t respond promptly, especially when they’ve made it clear that the project is urgent). It makes sense, right?
Pro-Tip:
After sending a proposal for an urgent project like this, make sure to keep your Upwork status set to “Available” to increase your chances of being contacted by the client. The green dot should appear next to your profile photo.
One way to do this is to keep the Upwork tab open in your browser and periodically interact with it—such as scrolling or clicking every 5 to 10 min—while you focus on another task.
If your client does reach out to you, drop everything you are doing and just type “Hi!” within a few seconds to let them know you are ready to start the chat RIGHT AWAY. Don’t waste any seconds by typing anything else which you can do later.
If you sent a proposal like this and didn’t get a job, don’t get upset – Unfortunately, if someone else with better ratings/experiences/qualifications than yours also submitted a cover letter as good as this one, your client doesn’t have a logical reason to hire you instead. You should just move on and keep applying because the more you submit, the better chance you get 🙂
Example 2: A Long-Term Project with a Reasonable Hourly Rate Seeking Highly Specific Skill Set/Experience
I recommend not applying for this type of job until you have 5-star ratings (with positive feedback) from at least three different clients and a 100% Job Success Rate. The status badge “Rising Talent” or higher would also be a plus. Since this type of job is very popular, you will be competing with many experienced freelancers who have better ratings and status than yours, which puts you at a disadvantage in this competition, even if you have a fantastic cover letter.
That being said, let’s move on to the second scenario.
Let’s say there is a job posting for a 3-month project with an hourly rate of $15-$30, requiring up to 40 hours a week and needing a very specific skill set and experience. The job description includes many technical details as well as a long list of required qualifications.
For this type of work, a cover letter from Example 1 obviously won’t suffice. Why? Because this client will be much more selective about whom they hire, so you need to convincingly demonstrate in your cover letter that you are qualified and meet their expectations.
The client will likely review the proposals from all candidates, ensuring they select the best of the best for whom they will invest a significant portion of their budget for three months.
Given the situation, a more appropriate cover letter would look like this:
Hi there,
This is <Your Name> from <Your City, Country>. I’m a <Your Job Title> specializing in <Whatever is closely related to the project> for the past <Number> years, with a background in <Whatever your experience/education is that is required for the project>, including <Example list that would really impress your client>.
I believe I’m fully capable of excelling in your project because:
* <Detailed information on how you meet ALL the qualifications listed in the job posting>
* <An explanation of how deeply experienced you are in the field>
* <A success story of a relevant project in the past and how impressive the outcome was>
I look forward to hearing from you!
Best wishes,
<Your Name>
This cover letter should address the client’s needs by determining whether you have the relevant qualifications and experience, what time zone you are in, the likelihood of you excelling in the job, and finally, whether you appear to be trustworthy.
Now, the important key factor here is to make this letter totally tailored to this specific project and you can’t mention anything irrelevant to this project (clients can often tell if you are just copying and pasting some cover letter template).
Pro-Tip
If the job posting contains a link to your client’s company homepage or an attachment for reference, be sure to review it closely. Then, casually mention something you found in that resource in your cover letter to demonstrate how much you care about this project without directly stating it to your client. This method leads me to win many jobs including a $20K+ project, so it is a proven method!
From the 2 examples above, I hope they gave you an idea of how you could adjust the style in your cover letter for the type of job posting you’d like to apply for. It’s not free to apply for projects on Upwork (you need Connect points), so make each one count by really taking the time to perfect your cover letter to increase the chance of getting the job!
Tip #2 on Upwork Cover Letter: Give Value First
When clients read cover letters, they all have one thing in mind: “What benefit do I get by hiring you?”
If you’re a beginner, what can you offer that sets you apart from experienced freelancers? Since you’re likely less busy than those juggling multiple projects, you could provide lower rates, prompt responses, and a flexible schedule. But have you considered this effective strategy? Offering a high-quality FREE sample!
If you don’t have enough ratings, feedback, Job Success Rate, or experience on Upwork yet, you should definitely offer a free sample—something you can complete in about an hour, just to prove to your client that you actually have the skills you claim in your profile and cover letter.
You can say something along the lines of:
To demonstrate my ability to excel in this project, I would like to offer you a FREE sample of my work, which includes <detailed information on the sample you can provide>.
Please feel free to assign me a small project of your choice, and I will respond within <number> hours of receiving the sample project.
If the client likes your offer and accepts it, make sure to deliver the highest quality of your work so that your client would be eager to hire you!
Tip #3 on Upwork Cover Letter: Use AI to Proofread/Edit
This may seem obvious, but your cover letter must be free of typing and grammar errors. Clients are often exhausted and stressed from reviewing numerous submissions. If your cover letter contains errors, it becomes difficult to read, adding unnecessary stress for your potential client. Additionally, such mistakes can undermine your professionalism and trustworthiness, making it essential to avoid them.
Fortunately, we have access to AI technology, which we should leverage to its fullest potential. I use ChatGPT to proofread all my cover letters and request edits as needed to ensure they sound professional. This approach not only corrects typing and grammar errors but also enhances the overall flow of your sentences in a professional manner.
Pro-Tip:
When you copy and paste the sentences produced by an AI, ensure that you only copy the refined version of the cover letter and nothing else, such as a message from the AI that says, “Let me know if you need any further adjustments!”
Summary
Thank you very much for taking the time to read my blog, and I hope you learned something new.
It may take some time to write a cover letter in the beginning, but you’ll get a hang of it pretty quick and eventually you’ll be a master of creating your cover letter!
If you are interested in how I made my $30K on Upwork in less than a year, please read my blog page below:
Related Articles:
My Upwork Success Story: $30K in Year One with Minimal Experience
I hope you’ll have a successful journey with Upwork, good luck to you!
