3 Proven Upwork Proposal Examples Written by a Six-Figure Freelancer
Morgan OverholtThere’s no shortage of people on the internet ready and willing to offer advice on writing Upwork proposals. But you may have noticed that few are willing to "put their money where their mouth is," especially when it comes to providing proof of their own Upwork earnings—or more importantly, proof that their proposals work. But today, reader, you’re in luck. I’ve earned over $600,000 on the Upwork platform, and I’m going to share five real Upwork proposal examples that have earned me hundreds of thousands of dollars on the platform.
An Upwork Proposal Checklist
Before we dive into the examples, here’s a quick reference checklist to help with your proposal-writing journey:
I believe every Upwork proposal should include some combination of the following elements:
- A confident understanding of the requirements
- Details about the job description
- A genuine interest in the work
- Your professional qualifications
- A unique selling point
- A link to an off-site portfolio or your Upwork profile
- A call to action
I’m also a firm believer in non-templated, non-AI proposals (unless you’re just using AI for grammar and spelling checks). As someone who has also played the role of a client on Upwork, I can tell you from personal experience that most freelancers send generic proposals without actually reading the job post. This is why referencing specific details about the job and customizing your proposals and cover letters will make you an instant standout.
The Proposal I Used to Win My First Job
Whether you’re a new freelancer or just new to Upwork, landing that first client on the platform can feel impossible. Trust me, I’ve been there.
It took me almost two weeks and dozens of applications to see my first “nibble.”
This is the proposal that finally worked:
Hi! I am new to Upwork, but I am a 15-year veteran in the graphic design industry. Because I am so new to this site, I am in need of a great review to add to my profile. And because of this need, I have gone the extra mile for your project. In fact, I have already completed the job—converted your image into a vector and made the requested changes to the running man. I will remove the watermark if you choose me for the job and send you the vector file immediately in exchange for a glowing review. Please check out my profile for additional examples of my work. |
I then attached a watermarked screenshot of the completed project to the proposal. Admittedly, this method was unconventional and a bit risky. However, since I was able to complete the task relatively quickly, I figured the only thing I had to lose was my time. Going the extra mile for this proposal earned me a near-immediate response.
While I’m not encouraging you to complete the entire project as I did, think about ways you can offer your prospective client a bit of a “free sample”—perhaps something like a rough sketch or outline.
Those who go the extra mile will have an easier time landing the job.
Key elements that made this proposal work:
- I proved I was fully capable of doing the job.
- It's short and sweet (no fluff).
The Proposal I Used to Win My Biggest Job
This client had all the red flags—red flags that would make most freelancers run for the hills.
- They were new to the platform with no hiring history.
- The entire job post was a single line.
- They asked for free work when they replied.
But seasoned freelancers like myself know that these “red flags” don’t have to be deal-breakers. In fact, sometimes you can find “diamonds in the rough” with these types of clients, as others are passing them by—meaning less competition for you.
I took the chance, behaved professionally, and kindly explained to the client that “free work” is prohibited by Upwork’s Terms of Service. I received no pushback whatsoever and went on to earn over $158,500 from this single contract.
In fact, this would end up being only the first of many projects with this client. I still have an open contract with them today.
This was the proposal I sent:
Hey there! I am a graphic design guru with 15 years of professional experience. I work with nationally recognized clientele on a daily basis, including the Centers for Disease Control (CDC), QuickBooks Intuit, and Kimberly-Clark (Kleenex). I have a hybrid background in graphic design and sales, and I am able to work with a variety of mediums, including digital, print, and of course, graphics, banners, and packaging. I am also FAST and pride myself on my ability to offer quick turnarounds. I will attach a few design examples to this proposal. You can view additional work samples on my Upwork portfolio. If you have any questions at all, feel free to reach out! Looking forward to hearing from you soon! Morgan Overholt |
This is one of my favorite proposal formats because it highlights my experience as a professional in my field. It contains a unique selling point—my quick turnarounds—and also features a sales technique known as the “presumptive close.”
The presumptive close is where the freelancer assumes the client is ready to close the deal. Instead of saying, “Let me know if you’d like to hop on a Zoom,” I say, “I’m looking forward to hearing from you soon.”
Mastering the art of the presumptive close can be a game-changing technique for both Upwork and real-world clients alike.
Key elements that made this proposal work:
- I applied for a job other freelancers ignored.
- I established myself as an expert in my field.
- I provided a robust portfolio with multiple viewing options.
- I used the presumptive close technique.
- I included my full name (in case the client wants to Google me).
The Proposal I Use Today
As I said earlier, I don’t believe in “templated” proposals, so there isn’t a single format I stick to for every proposal. But this one should give you a general idea of how I tend to approach things.
There has never been more spammy, automated proposals on Upwork than there are today. I largely blame the proliferation of AI writing tools.
With that in mind, I now keep my proposals brief, direct, human, and highly personal.
Here’s a proposal I used to win one of my most recent jobs:
Hi there! I do this kind of work all day. I even work with a variety of nationally recognized supplement brands on Amazon, including EN-1. I'm used to working on labels and mockups. I'd love to knock those edits out for you. I am attaching a multi-page PDF portfolio to this proposal. You can view additional work samples on my Upwork profile. Shoot me a quick message here on Upwork today and we can get started! Morgan Overholt |
I know Upwork clients don’t have time to read through dozens of spam proposals. So getting to the point, and proving that you’re a real human being who has read and understood their job post, is crucial.
This proposal does a great job of providing a specific real-world example and proof that I am both competent and capable of performing the task at hand.
It doesn’t waste any time and gets straight to the point.
And again, notice the inclusion of my presumptive close: “Shoot me a quick message here on Upwork today and we can get started!”
Key elements that made this proposal work:
- It's brief and to the point.
- I establish my ability to do the specific job at hand.
- I provided a robust portfolio with multiple viewing options.
- I used the presumptive close.
- I included a CTA (call to action).
Are you currently having issues winning jobs and writing proposals on Upwork? Drop your questions and comments below.
3 comments
If you don’t have a portfolio – make one! Give yourself a project. Offer free work for friends and family. Start your own side hustle be your own client. You need to offer some proof you’ve performed the job before.
If you’ve never performed the work before – you have no business offering it to others.
What if I don’t have a portfolio to show for my skills?
This is it! You always need to show value, there is no way around it. Great job! I also learnt a thing or two 🎉