5 Uncommon Upwork Proposal Cheats: Write a Cover Letter that always Wins the JOBS!

Sunday Abegunde
Freelancer Tips
Published in
4 min readJan 18, 2023

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My name is Sunday, and I am a Top Rated Plus freelancer on Upwork, which means I have made AT LEAST $10,000 on Upwork within the last 12 months. Shh! I have made way more! And some of my five biggest Upwork proposal tips are what I will share right now.

Sunday, am I actually doing this right now?

Photo by Juan Rumimpunu on Unsplash

Hmmm, it’s part of my promise to reveal freelance secrets to my channel subscribers on YouTube, so let’s jump right into it.

1. Stand out with a USP:
Put something that hooks them early in your proposal. For example, a real estate firm in the US needs a video editor. Amazingly, I studied real estate for four years at the university. I smartly used this as a hook in the first three sentences of my Upwork proposal. That job had other proposals from other video editors, but I won it because I leveraged my USP. Do this too. This can help you stand out among other proposals and increase your chances of winning the job.

2. Client Research:
Aside from personalizing your proposal to the client using his or her details you can find, always check previous clients’ reviews for the client’s name. You can also check their previous client reviews to get a sense of what they’re looking for in a freelancer.

I have a video that elaborates more on Upwork proposals, which will help you understand this Upwork proposal thing better: https://youtu.be/rY51KVEYQbo

Photo by Aarón Blanco Tejedor on Unsplash

3. Client’s Pain Points:
Demonstrate that you understand the client’s exact pain points. Pain points are difficulties or challenges experienced by your Upwork client. Put yourself in your client’s shoes. For example, the client may be under time constraints and cannot afford to hire a trial-and-error freelancer, or the client may need to make sales. Empathize with the client and demonstrate to the client that you know what is at stake for them. Emphasize your efficiency and ability to deliver results. This can help create a sense of urgency and increase the likelihood of them hiring you. Don’t forget to infuse two CTAs into your proposal.

4. Establishing Authority and Value:
Clearly outline the value you can provide and what sets you apart from other freelancers. Share your specific experiences and relevant samples that prove you are the best fit to provide for the client’s needs. If you have any points that establish you as an authority in the field, be sure to include them in your proposals. If you don’t blow your whistle, who will?

If I don’t tell you about the 100% free videos I created to help you supercharge your Upwork game, who will? Tap here to subscribe to my channel now: https://www.youtube.com/channel/UCBtepvre3ERD-hG7f-dSL0Q

5. Clients’ results and reviews:
Include results from previous clients to back up your claims right in your proposal. Extract two sentences from previous client reviews that are similar to the project you’re sending a proposal for and attach them to your proposal. Attaching samples is great, but downloading wearies out some clients, and attaching links is better, but some clients are skeptical about links. Hence, to play it safe, do both.

Thanks for watching. We have come to the end of this Upwork class…

Photo by Frugal Flyer on Unsplash

But if you’d love to make an extra $2000 monthly on another platform. This is an after-class bonus:
Open a clickbank.com account, select a product of your choice and get your Affiliate link. Open a Quora or Medium account. Use Chat GPT to create helpful content in a niche that can sell the product. For example, if you choose the product, Back to Life, you can create content around exercise & fitness to get free organic traffic. Don’t post your affiliate link directly to Quora, Medium, or any other blog; instead, create a free landing page with site.google.com and direct traffic to the affiliate link by adding your landing page’s link to the content on Medium or Quora. This is an automated system where you can make some bucks.

Actually, I should have charged to teach that, but never mind. Simply tap and LIKE this video to show your appreciation.

I’d see you in my next video!

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Sunday Abegunde
Freelancer Tips

Congrats! I'm your guide on remote jobs, side gigs, & freelance jobs, being an Upwork Top Rated Plus Freelancer myself. Follow me. 🌎 Linktr.ee/speakingpen.