Al Anany

A Killer Upwork Cover Letter

Photo by Patrick Fore on Unsplash
Photo by Patrick Fore on Unsplash 


This Upwork cover letter landed me a $4,620 one-week job.

There are good Upwork cover letters and bad ones. Then there are the ones that do the job.

I freelanced on Upwork for almost 3 years. I’ve made over $100k working there. Say what you want to say, Upwork has shown me a huge variety of clients from all over the world. Although I currently have my problems with Upwork, that doesn’t change the fact that I’ve met numerous talented clients and entrepreneurs.

A pizza cook learns how to improve his pizza over time. A doctor learns how to heal more efficiently. Similarly, A freelancer learns more every day about client psychology. Your wallet is connected to them, thereby, you’ll need to ace your understanding of how they think.

For Upwork, your initial first contact is one of the things that matter the most – the cover letter.

You can read tons of articles online about how to write the perfect cover and how to present yourself in the best possible way.

Here are two things you need to always remember.

  1. You need the client.
  2. The client needs you as much.

If you believe the market is saturated with freelancers like you, then you should know that the market is saturated with clients as well.

“The Global Freelance Platforms market size is projected to reach US$ 9.19 billion by 2026, from US$ 3.39 billion in 2019.”Reference

Simply, that indicates that the wallets are increasing in number and size.

That’s the first and most important hindering factor to keep in consideration as a freelancer. Value yourself, you’re on the same boat as the client. You’re not entering the lottery and wishing for a win. You’re checking whether both of you are a match. If not, there are others.

One of my recent cover letters was with a client that I knew I was perfect for what he needed.

Client’s Job Post: Top-rated pitch deck expert needed. Can you help us crack the Saudi Arabian investment market?

Here’s what you should know:

  1. In my line of work, pitch decks are works of art. I love doing pitch decks compared to business plans. Pitch decks make your mind think of the investor in the best possible way. In order for the deck to be successful, you need to understand the investor. Hence, that’s one of my highest interests.
  2. I’ve lived in Saudi Arabia for around 18 years, so yes, I am sure I can help them crack the market there.

Emotionally, I was pushed to apply to this. That’s dangerous. Because one should not apply to an Upwork job post with any emotion. It should be pretty logical. (Think of Star Trek’s Spock, he would be the highest-earning freelancer of all time.)

I took my time, then constructed and sent the following:

Upwork Cover


Here’s what I did:
  1. I sent the client to my website. My website showcases the quality he’ll be expecting more than anything.
  2. I made it very brief and to the point. It clearly shows that I know something about the gulf investment market. When the client sees this, the question will present itself, “What does he know about the gulf market?” – and that’s the direction I want the conversation to be directed to.

That was more than enough. We scheduled a call and worked on the deck. The actual work on this deck was a pure one week of extensive work. Yet, as any freelancer would know, the timeline is usually stretched in such jobs to work on the design and minor modifications. (This one extended to about 5 months. Yet, it doesn’t matter, because why would I want to end a relationship with a good client?)

Upwork Cover

The work, as expected, was a great product. Mainly because of my interest in the market, and the industry. Therefore, It was a correct match.

You’ll have to feel the room when it comes to each client. However, what is guaranteed, is that the more time you spend in the freelancing industry, the more clients you get, the more you learn about client psychology.

The recipe of the perfect Upwork cover letter is similar to the recipe of the best potatoes. Some like them mashed, others like them baked. As much as possible, don’t give a french fries lover, a mashed potato dish.

How would you be able to perfectly predict that?

Careful observation, and time.

I’m Al, a business consultant in Zurich, Switzerland. I believe in providing readers with value. Hence, I created Learn, a section on my website purely dedicated to guides and articles providing value in the fields of Freelancing, and Entrepreneurship. Alternatively, you could visit my journal for all my articles, or my Medium profile.