How to write a winning proposal on Upwork and land more jobs

A Step-by-Step Guide to Writing a Winning Upwork Proposal

My blogger friend Amanda Cross, the voice behind The Happy Arkansan and reached out to me with this terrific guest post on writing a winning Upwork proposal.

She’s an Upwork pro, and after talking with her one-on-one in my recent podcast episode, I have been dying to learn more about her Upwork secrets. I consider myself a pretty experience freelancer, but I still haven’t tamed the beast that is Upwork. Today, she’s sharing her step-by-step guide to writing an Upwork proposal that lands you the gig. 

Want to listen to the podcast? Here ya go! It’s full of even more tips.

When it comes to freelance job hunting websites, Upwork seems to get a less than stellar reputation. Upwork’s reputation precedes them despite the myriad of reputable companies and entrepreneurs who use the platform to hire freelancers from around the world.

If you are struggling with writing a winning Upwork proposal, I hope that today’s article will teach you the ropes. I have been using this platform for nearly two years now, and I want to help you start seeing some traction on the site.

1. Find the Best Jobs on Upwork

The first step to writing a winning Upwork proposal is to find a job that makes you excited to apply. You can’t expect to win many Upwork jobs if you don’t start with that simple step.

Here is what I usually do to find jobs I want to apply to. First, visit the site at least twice per day, Upwork has many employers, so the site changes rapidly, even on the weekends.

Once I am on the site, I deploy my usual filters:

  • Category: Article & Blog Writing
  • Client Info: Payment Verified
  • Client Location: United States (sometimes Canada)

From there, I usually browse until I find something that’s worth my time. Over my time using the Upwork platform I have grown an extremely thick skin. I know what I am looking for, what I want to accept, and I ignore the rest. That’s why I only view certain client countries, and I narrow my search to look at clients who have verified their payment methods.

Overall, you need to know that there will be low-paying clients. Many clients won’t want to pay you a decent wage, and that’s just something you need to accept. Low paying clients is not an Upwork problem; this is a work culture problem (especially in America.) Most people have been taught to value lower prices, even if it cuts down their quality substantially.

Just because you accept that there will be low-paying clients on the platform, doesn’t mean you agree to that payment for yourself. There’s a time and a place for clients who don’t pay much. What they charge won’t affect your worth or what you can charge.

There are plenty of clients who don’t mind paying a bit extra, you just need to dig to find those people. Look for clients who are ready to pay intermediate or expert prices, and you can usually find a client who is prepared to spend more money. You can also scroll down on a job description to see the client’s recent history so you can get a better idea of the rates they pay freelancers.

Writing a winning upwork proposal

2. Read & Understand Upwork Job Descriptions

After you find a job that looks promising, it’s time to do your research. You need to understand what they’re looking for and how you can help them achieve their goals.

Don’t spend all day doing this research, a bit of sleuthing will do. For example, if I want to apply to write a blog post on “how to become a better boss,” I am going to do my research to make sure I can write an article like that, especially one that’s better than competitor blog posts.

So, if you find an online job that you want, dig deeper. Understand how you can help them before you jump into your regular spiel. I have a few statements that I rotate through when writing a winning Upwork proposal, but even then, I try to customize at least a few of the lines for that person. Understanding the job description is essential so that you can customize proposals.

Also, sometimes you will get potential clients who want to test that you have read the entire job description. They may have extra requirements or phrases tucked into the description to make sure that you have done your due diligence. It doesn’t hurt to be thorough!

Bonus: check out their website if you can!

While you’re doing research, check out their website if possible! It’s not always included in the summary. If they include a website, you should always check it out to see if you’d enjoy working for them.

While checking out their website, you may also see if you can make any connections with them based on their site that you can bring into the application. It’s always good practice to view the website of who you’d be working with if you have the opportunity to do so before you apply.

3. Answer Supplementary Questions First

Okay, this is the most critical piece of information I will probably ever tell you about writing a winning Upwork proposal. Your potential clients don’t read the cover letter first. Upwork shows them the answers to the supplementary questions first, then your cover letter.

Many new Upwork freelancers mess up because they answer the cover letter section first, then they are burnt out and give crappy answers to the main events: supplementary questions. I know that I am personally guilty of focusing too heavily on the cover letter, thinking “It’s a cover letter, it’s obviously first!”

Trust me when I say to focus on those extra questions first if your potential client asks them.

4. Start Your Upwork Proposal About Them

People are self-centered. They are more interested in hearing about them before they are interested in hearing about you. They want to know:

  • What have they done right?
  • Do you find their blog interesting?
  • Can you tell that they have been putting a lot of effort into their website?
  • Are you excited about the work they are doing for the community?

I know, this seems like a strange way to start your cover letter, but they likely want to be the center of attention in a sense. It gets them interested in hearing what you have to say and it shows that you’ve done your research. Your first couple of sentences should focus on them and building a relationship.

Write a winning upwork proposal

5. Show Prospective Upwork Clients You Know Your Stuff

One thing I love to do when creating a cover letter is to talk about my knowledge of the topic they need help with. Showing your knowledge helps no matter what job you are applying for. Give them a little something they can either use for free or just a general statement.

For example, if they are an entrepreneur starting their blog, you may want to give them a piece of advice on what has worked best for you when starting your blog. Give them something of value they can sink their teeth into because this shows off your expertise and makes them want to hire you.

6. Talk About Your Skills

The next thing you need to do is talk about you. What makes you qualified to be their blogger, coder, social media guru, virtual assistant, etc.? Why should they trust you?

Honestly, you never know what kind of past freelancer baggage this person might have. You want to make sure that you are putting your best foot forward, so you can get the job and rise above any of the noise the client may be dealing with.

What should you share with clients on Upwork?

  • Your expertise in their subject area
  • A similar project you have worked on and results from that project
  • One of your best client reviews that showcases your best work
  • Any projects with your name attached that you have the right to share

You want to make sure that the client walks away with a clear picture of who you are, how awesome you are, and how you can help them.

7. End Your Proposal with a Call to Action

I like to end each proposal with a call to action or CTA. A call to action is a device or phrase that you use to invoke an action of some sort. The action you want is to be moved into the interview phase of the Upwork hiring process. Here are some CTAs I’ve used:

  • I look forward to hearing more about this project to see if we’d be a great fit working together!
  • I would love to chat more about this opportunity as I feel like I can create great content for your website. Thank you so much for the chance to apply for this position!
  • I would love to chat with you more about your project! I am excited that you want to produce such a lengthy guide on a platform I love so much!

Ideally, you want to prime them for asking you more questions about how you can work together. Being able to chat with them further will usually help increase your chances of getting hired.

I typically ask for more information about the project or to talk further. These are actual CTAs I have used in the last few months to get hired on a few of my latest Upwork jobs.

The Best Tips for Landing Jobs on Upwork

To end what I hope was already a super helpful article on writing a winning Upwork proposal, I wanted to touch on a few more of my best tips for landing jobs on Upwork.

It’s not always about turning in a great proposal! I hope these tips help you with other aspects of the site.

1. Create an Amazing Upwork Profile

Upwork has a HUGE “underground” work culture. Many of the jobs get set to private and sent directly to the freelancer the client wants to work with based on prior experience or even the freelancer search tool. You should spend time working on your profile and making it shine.

You also want to make sure that you treat your profile title like an SEO magnet. Many Upwork clients use the freelancer search tool to look for freelancers, and if you have a great title, you could find yourself higher in the search results, which means more people landing on your profile.

How to land gigs on upwork

2. Ask Upwork Clients for More Work

You don’t need to continually be on the lookout for more clients, as long as the clients you currently have keep giving your work to do. Once you find a great client, don’t let go!

You can ask if they need more assistance, and then you have a way to continue delivering stellar work. Plus, the more money you make with a particular client, the fewer fees you pay to Upwork. Just by making $500 with a client, you shave off 10% of the fees you pay to Upwork, These add up to more money in your pocket.

3. Close the Upwork Account to Get Reviews

If your client doesn’t have anything else for you to do, the next best thing you can do for your Upwork career is getting a review from that client. Encourage them to close the account and review your services. Let them know that you loved working with them and that them rating your services will help you keep working with other excellent Upwork clients.

Please do not close accounts without at least discussing getting a review from your client. Trust me! I am still trying to pull my Upwork job success score up because I had a couple of less than stellar reviews and a ton of closed jobs with no reviews. Always strive to close accounts and get a review in the process!

4. Avoid Burnout When Applying to Upwork Gigs

Upwork is not the place to burn yourself out on applying, especially if you are not landing many jobs from it. Upwork does regularly remove profiles, and a lot of that profile removal happens when your particular set of skills don’t seem to be needed on the platform.

This is scary for anyone to think about, especially if your goal is to make money online, though I am sure it doesn’t happen all the time. So, don’t mass apply unless you are putting thought and effort into each application. Upwork is a numbers game in a way; you want your skills to be seen as helpful to a number of Upwork clients.

I would encourage you to use your connects to apply to freelance jobs smartly. Don’t use the spaghetti approach when it comes to applying for positions on the platform! This is even more true with the new $0.15 cents per connects rule.

How to Write a Winning Upwork Proposal

There you have it, folks! My best tips for writing a winning Upwork proposal. While these tips won’t work every time (no one has time for that many jobs anyway), they’re a great way to gain an edge on other freelancers making money online with Upwork.

I hope that this will help you start seeing more success from this platform. Upwork does get a bad rep because the platform isn’t as well vetted, but I feel that some true gems use Upwork to hire. I have virtually met some genuinely cool and inspirational people freelancing on the platform, and I know that you can too. There is SO much work to go around on the platform, we all have a seat at the table.

If you want to see more freelance related content from me, check out these articles:

Amanda Cross is a blogger and freelancer from Arkansas. She is living her dreams, writing content for companies all over the country, from the comfort of her living room. Amanda loves short walks to get ice cream and helping millennials figure out the random parts of adulting she’s somehow managed to grasp. You can follow Amanda for more of her tips and tricks on her blog, Instagram, Twitter, Facebook, and Pinterest.

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Hey, I'm Sam! I'm the blogger and full-time writer behind Samanthability. I blog about starting your own blog and rocking post-grad life. You can find me exploring Seattle, binge-drinking iced coffees, and reading spicy romance books. I'm glad you're here!