Six Steps to Writing the Perfect Upwork Cover Letter

Six Steps to Writing the Perfect Upwork Cover Letter

By Rob | March 1st, 2016 | 20 Comments
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To succeed as an Upwork freelancer, a great cover letter isn’t optional. It’s crucial.

The moment a job is posted on Upwork, it becomes visible to thousands of people who do exactly what you do. And unlike your middle school gym class, you aren’t competing against 20 neighbors with similar abilities.

You’re applying to the same projects as skilled  $3/hr Filipino writers, $300/hr startup experts from Silicon Valley, and award winning Forbes contributors.

The only way you can land any of these projects is to set yourself apart. And one of the most effective ways to stand out from the competition is to create a killer Upwork cover letter.

Related content: Maximize your income with this free freelance rate calculator.

How to create an attention-grabbing Upwork cover letter

How to Create an Attention-Grabbing Cover Letter on UpworkAs an employer sorts through candidates to find the right fit, the first thing she sees is your cover letter. If it impresses her, you have a good chance of winning the contract. However, if the cover letter is poorly constructed or generically copied-and-pasted into the application, she will move on – and your profile won’t get a second glance.

I’ve won over 50 contracts on Upwork during the last couple of years – with many worth thousands of dollars. After a plethora of “trial and errors”, I’ve discovered how to win more clients than I can manage – for both myself and several other writers.

Here’s how I won over 50 Upwork contracts.

If you do quality work, but are still unable to find new clients, the issue probably has to do with your cover letter.

Add these six elements to your Upwork cover letter and watch the interviews roll in.

1. Start by sharing your qualifications

Why are you more qualified for this project than the other twenty applicants?

If the client doesn’t see a reason to keep you around right at the beginning, they will rapidly move on to the next candidate.

So establish yourself as a professional. Do you have a degree? State it here? Have you worked in the industry? Now’s the perfect time to state this.

But keep it short! If this goes on for more than two or three sentences, you’re going to lose it. The point isn’t to toot your own horn, but to show why you are the right fit for this position.

Here’s how I state my qualifications for a business blogging project:


Hi, my name is Rob and I have an MBA, experience in financial analytics, and have written content for over 50 highly satisfied clients here on Upwork – as you can see from the “Top Rated” freelancer badge on my profile. 


Although it’s a long and slightly wordy single sentence, it sums up who I am concisely.

Notice how I focus much of the attention on how I can benefit the client. I have business knowledge (MBA and work experience), keep my customers satisfied (beneficial for them), and am one of the Top Rated freelancers on Upwork (which means they will be getting the best).

I also leave a lot out. What you leave out of your cover letter is just as important as what you include. For a business client I don’t mention that I’ve traveled to five continents, am involved in my church, and love sailing the San Francisco Bay. Although I may mention those items for another project.

Ultimately, you want to tell the client why you are qualified for their project, but concisely enough to move on to the rest of your proposal.

2. Make it personal by asking a question

When possible, try to connect with the client – very briefly.

If they include a link to their website, this makes it easy. Otherwise, see if you can pull something from the job description itself.

I’ve noticed that asking a question works best.

Asking a question is essential – whether at this point or at the end of the application. Why? Because it encourages the client to contact you to respond to your question.

If someone contacts me on Upwork, I have a 50% chance of getting the job.

I seem to get about 50% of the jobs that I am contacted for. Once the client reaches out to me, I can learn more about what they need and present myself as the perfect candidate.

Therefore, encouraging that initial contact is essential. And because we all love talking about ourselves and what we do, asking a question to make it personal is a great way to start a conversation.

Following suit with the same application, I would make the cover letter personal by saying something like:


Your job description mentions your company is in New York. Are your customers exclusively from NY or do you work with clients nationally/internationally?


Although nothing profound, this simple question treats them like a person I am interested in getting to know – rather than just a client I am trying to land. It’s also a question that helps me learn more about their needs and how I might be of assistance. Finally, it encourages a response on their part.

And that’s the most important piece – so I’ll say it again:

Once you get a client to respond to your Upwork cover letter, your odds of winning the project increase exponentially.

3. Explain why you’re interested in this project

Most projects on Upwork come from clients who are passionate about what they do. Whether they’re entrepreneurs or project managers, they have a vested interest in the success of their project.

This means that they are in love with their project. Whether it’s a website idea, a new app concept, or simply a poster to promote their band – the client is excited about this project.

And you should be too.

By sharing with the client why you want to work on their project, you’ll set yourself apart from the plethora of freelancers on Upwork who are simply trying to land their next job.

As with the other elements, keep it short – but a well-worded sentence can make a world of difference.


As you can see from my own blog, MoneyNomad.com, I love writing about entrepreneurship and would thoroughly enjoy researching and developing blog posts for your website.


This simple sentence reveals that I am already an expert on this subject and will be just as excited about this venture as the client is.

4. Share examples of similar projects

This is HUGE! Although more and more freelancers on Upwork are showing links to their past work – there are still too many that don’t.

If you have previously published work – share links to it in your job posting. Even if the projects are on your own blog or developed under someone else’s name, it still shows a level of credibility and gives the user a feel for what they can expect from you.

If you don’t have any samples, then you probably shouldn’t be trying to sell yourself to someone else. Instead, focus on building up a portfolio of 1-3 items that you can share. Do this by offering your service inexpensively on Fiverr, starting your own blog, or writing a few articles on HubPages.

I have a wide enough collection of articles that I’ve written, that I can usually find some worthwhile samples. But if I can’t, then I’ll share related content with voice I think the client wants. And I’ll share ghost written content as well.


Here are some samples of articles I’ve written in the past:

http://www.happyfox.com/blog/gamification-employee-engagement/

http://www.huffingtonpost.com/entry/57e4746fe4b00267764fbcbe

http://moneynomad.com/6-ways-to-live-on-under-10000-a-year/


Because Upwork doesn’t allow you to add hyperlinks to your job proposals, you’ll need to add in the entire url. Also, include a space between each url so that it’s easy for the client to copy and paste into their browser if necessary.

5. Vaguely explain your rate

Sometimes I state my rate right upfront, but other times I provide a ballpark figure or don’t share it at all in the cover letter.

Ultimately, when it comes to stating your rate you want to keep two things in mind:

  1. Encourage the client to make contact (remember, I get 50% of contracts once a client interviews me).
  2. Prevent yourself from wasting time with clients looking for cheap work.

From a freelance writer’s prospective, there are ample projects that want a writer willing to develop articles for $10-25 a post. This is far too low for me – and I really don’t want to waste my time interacting with someone not willing to meet my rates.

However, if I state my rate at $0.30/word when someone else offers to do the same project for $0.15/word – they may not make contact with me, allowing me to negotiate a rate and level of quality that meets their needs.

Depending on the client, I will say something like this in the proposal:


I generally charge my B2B clients $0.30/word. However, because I enjoy writing about entrepreneurship and think your project would be a lot of fun, I may be able to reduce my rate slightly.


By stating the higher end for my blogging rates, and then mentioning that “I may be able to reduce my rate slightly”, the client will understand that I don’t write $10 articles, but he will recognize that he may not have to pay $150 for 500 words either.

If we ultimately agree upon $0.20-0.25/word, the client feels like he’s getting a steal. Win-win!

6. Offer something for free

If you’re confident in the service you offer, then offering an initial trial for free can help you make a lot of money.

Particularly when you are new to Upwork, and competing with freelancers with a large portfolio and high reviews, providing a free trail offer is a great way to get started.

If you’re a freelance writer, a 500 word article won’t take you more than 1-2 hours – so offering one for free is certainly worth the potential of ongoing work.

For one-off projects, like web-design, this could be a bit more difficult. But it’s not impossible. Rather than doing the entire site for free, offer to do an analysis of their current website, a review of their top competitors, or a 30 minute mock-up of what their website could look like.

Once you’re established, offering work 100% free isn’t necessary, but it can still help to offer a “freemium” version of your work. An example of how I do it:


Finally, I would like to offer you a trial article risk-free. If you like it, you can pay for it and use it. However, if it doesn’t meet your expectations, you are welcome to improve upon it and use it for free. What topic would you like me to write about for this first post?


Other times I simply offer to write the first article for free in exchange for recognition and a link back to my own website. Usually people would rather keep the content ghost written and focused on their website – so the end up paying anyway.

The book “Predictably Irrational” states that free is a powerful word. We all LOVE getting something for free. In fact, people are more likely to take a $0.10 Hershey’s kiss for free than they are to pay $0.01 for a $1 candy bar – even though the latter is actually a better deal!

Using this same psychology in your freelance work, and offering to do a free “mini-project”, is a great way to land your next client. On Upwork, or anywhere else for that matter.

The completed Upwork job proposal – Emulate this to land your next client

And here we have it! The completed Upwork cover letter – and one that has landed me tens of thousands of dollars worth of clients:


Hi, my name is Rob and I have an MBA, experience in financial analytics, and have written content for over 50 highly satisfied clients here on Upwork – as you can see from the “Top Rated” freelancer badge on my profile. 

Your job description mentions your company is in New York. Are your customers exclusively from NY or do you work with clients nationally/internationally?

As you can see from my own blog, MoneyNomad.com, I love writing about entrepreneurship and would thoroughly enjoy researching and developing blog posts for your website.

Here are some samples of articles I’ve written in the past:

http://www.happyfox.com/blog/gamification-employee-engagement/

http://bankvibe.com/how-saving-for-retirement-is-like-surfing/http://www.huffingtonpost.com/entry/57e4746fe4b00267764fbcbe

http://moneynomad.com/6-ways-to-live-on-under-10000-a-year/

I generally charge my B2B clients $0.30/word. However, because I enjoy writing about entrepreneurship and think your project would be a lot of fun, I may be able to reduce my rate slightly.

Finally, I would like to offer you a trial article risk-free. If you like it, you can pay for it and use it. However, if it doesn’t meet your expectations, you are welcome to improve upon it and use it for free. What topic would you like me to write about for this first post?


As you can see, it says a lot while still being relatively short. Additionally, it attempts to connect with the client and keep them engaged – from beginning to end.

Try this format the next time you write an Upwork proposal and let me know how it works! Finally, if you have additional suggestions for dominating Upwork, I would love to hear about them in the comments.

About Author Rob

Rob blogs at Money Nomad - where he shares strategies and tips for becoming a remote entrepreneur. When not working on his own projects, Rob writes articles for businesses and thought leaders. You can find him on Twitter @rlerich.

20 thoughts on “Six Steps to Writing the Perfect Upwork Cover Letter

  1. Why do you use “Filipinos” to compare? Idk, but it feels like you’re somewhat degrading us and you would like to discourage clients to stop hiring a filipino. Although your blog is good, I would really like to ask why.

    1. Hi Maria!

      Thank you so much for commenting. And I apologize if this article came across as degrading – that is not my purpose at all! The point I was trying to make is the diversity of competition that ALL freelancers have (regardless of where they are from). We are all competing with educated and skilled individuals willing to work for $3/hr – and freelancer celebrities who charge a premium, but have name recognition.

      My desire is for Money Nomad to be a website where online entrepreneurs and freelancers from ANYWHERE can come to learn and grow. Thank you for pointing this out. I included the word “skilled” in the sentence – and I hope that helps emphasize the true point I was trying to make.

      Thanks for reading and I look forward to seeing more of your comments in the future!

  2. Website mock-ups are called “spec work” and frownded up in web development community. Also, you won’t get away with using your website URL in the proposal for too long since it’s against Upwork’s TOS.

    1. Thanks for your response Ivan.

      Since I deal with writing, I am not fully familiar with an appropriate comparison in web design. Perhaps an alternative would be offering a 10 minute analysis of their current website – or providing a 30 minute brainstorming session regarding the design of their website. Ultimately, it’s about finding a way to provide value and begin developing that relationship. I’m actually going to write an article in the near future “praising” spec work from a designer – so be ready to come harp on that post in a couple of weeks. 🙂

      Regarding links in proposals – you are correct that, if you linked back to your design website, that would be against the TOS. However, linking to previous clients or samples is completely acceptable. Trying to prove that you were an exceptional designer, without providing links to your past projects, would be a very hard sell to make.

      Thanks for stopping by and best of luck with your future freelancing.

  3. Hey Rob, thanks for the tips. In my case, I’ve gotten some job offers and unto interviews but seems like the client goes MIA suddenly for a long period. Does it have something to do with my letter as well?

    1. Great question Denny! There are two possible things going on here.

      First, if you check the job posting you can tell how many interviews/hires there have been for the job. There is a chance that they interviewed multiple people and hired someone else.

      Second, check out my article How to Know Which Jobs to Apply to on Upwork – it may be that you are applying to jobs for clients who aren’t established. A lot of people post “maybe” projects on Upwork and never follow through.

      Thanks for your comment and let me know how I can help in the future.

    1. I am very honored Hersham! Thank you for joining. I will definitely make an effort to continue to impress. 🙂 And feel free to reach out if you ever have questions or thoughts for topics that you would enjoy. Now that you’ve signed up, my goal is to make it worth your time!

  4. I appreciate these tips for Upwork. I just landed my first contract there, I just enrolled last week. It has been a small learning curve trying to figure which clients are legit or phony, and I had to enter an interview with two of them to find some red flags like doing work outside the platform.
    Josh recently posted…April 2016 Blogging Weigh-InMy Profile

    1. I’m glad they’ve helped out a bit! But you’re right, there are certainly clients on Upwork that you have to filter through due to free work, outside of Upwork work, or simply low-paying requests. But there are definitely some good projects out there as well.

      Best of luck!

    1. Hi Waheed! It will certainly depend on your personal skills and the focus of the job. If you just copy and paste what I write, you probably won’t receive much luck. However, following that format can certainly be beneficial! Good luck and feel free to run a specific scenario by me if needed.

  5. Hi Rob!

    Thanks for the helpful article. What’s your advise for a newbie? Someone who has lots of experience in a traditional work but no freelancing experience. Do you have a published article on this topic?

    Thanks!

    Aff

  6. Hi, Alexandra here. You are not supposed to offer things for free on Upwork. It’s in the rules. That aside, I plan to use the rest of your tips to land my first job on Upwork. I plan to send in 5 proposals in the next two days!

    1. Thanks Alexandra! You’re absolutely right — you should do free work through Upwork. However, offering a risk-free trial project (that you could use/resell if the client didn’t like it) can help you land a lot more clients. Remember, this is a high risk for the client — what happens if your work is terrible and they’ve already agreed to pay you $2,000 for it? They’ve just lost $2,000. Therefore, if you are able to say that your first article/design/etc will only be paid for if they like it (with you keeping the rights to use it elsewhere otherwise), you’ll be able to reduce their hesitancy to buy. Thanks for the comment!

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