A Beginner’s Guide to Writing Upwork Proposals That Land Gigs

Most people confuse cover letters with proposals. And while they’re often used interchangeably, they’re coming from totally different places.

A cover letter is all about you, your skills, your qualifications, and your experience. It’s you selling yourself, explaining why you’re the best choice.

A proposal, on the other hand, is all about the client. Their problems. Their needs. Their goals. It’s you showing them that you understand what they’re dealing with and how you can help them fix it.

I didn’t realize any of this until I figured it out the hard way. My proposals weren’t getting any attention, no matter how many I sent. They were polite and professional, sure, but they weren’t hitting the mark. They were all about me—my experience, my skills, what I could do. But the client didn’t care about that.

I remember sitting at my desk, hitting “submit” over and over again, sending proposals that just seemed to vanish into thin air. It started to feel like I was throwing them out there, hoping they’d land somewhere. But they didn’t. I had the right intentions, I had the skills, and I wanted to help, but nothing was happening.

Then a friend of mine, who’d been freelancing on Upwork for a while, took the time to listen to my complaint. She didn’t sugarcoat it. “You’re doing it all wrong,” she said. She told me to stop writing cover letters. I thought I was writing proposals, but in reality, I was just sending cover letters.

“Write a proposal that’s about them, not about you,” she said.

That’s when she shared the simple framework that works. These five steps helped me go from being completely ignored to getting replies and gigs. Let’s break them down.

5 Steps to Writing Upwork Proposals That Land Gigs

1. Start With Empathy (Not Your Resume)

This is your hook. The first two lines decide whether the client reads the rest or skips your proposal.

Don’t start with: “My name is Alex and I have five years of experience in…”

Instead, start with something that shows you understand their problem: “Hey Sarah, I saw your post about needing help organizing your content calendar. I’ve worked with a few small business owners who were completely swamped and needed a system that works.”

2. Share a Quick Win or Relevant Experience

New or not, this is your moment to prove you know what you’re doing.

For example, instead of saying “I have experience with automation,” you could share a specific result like:

"In my last project, I helped a startup automate their Google Sheets to track expenses automatically. It took me just two hours and saved them days of manual work each month."

Approach like this makes clients want to continue reading your proposal even if you don’t have a big portfolio yet? That’s okay. You can still share:

• A small job you did for a friend
• A personal project you built on your own
• A process you developed out of necessity that helped you or someone else

Clients care less about your resume and more about what you’ve done. They want proof, no matter how small, that you can deliver on what you’re promising.

3. Mirror Their Language and Speak to Their Needs

This is where you show you’ve paid attention to the job posting. Use the same words they used to describe what they need.

For example, if the client says they need help with scheduling, inbox management, and data entry, you could say:

"You mentioned needing help with scheduling, inbox management, and data entry. I’ve worked on all three and have a streamlined system for each that keeps things running smoothly and error-free."

If they mention specific tools like Asana or talk about tight deadlines, mirror that language. It shows you’re on the same page and can handle what they’re asking for.

But here’s the thing: don’t lie. Only reflect their needs if you can deliver on them. When clients see their exact words in your proposal, it tells them you’ve read their posting and understand exactly what they need.

4. Make the Next Step Easy and Casual

Now that you’ve built connection and credibility, make it easy for the client to take the next step.

For example, you could say:

"I’d be happy to hop on a quick call or take on a small task to show you how I work, whatever’s easiest for you."

Keep it relaxed. You’re not desperate for the job, you’re simply offering help and making it simple for them to say yes. A lot of clients are hesitant to commit right away. By keeping the next step low-risk, you increase your chances of getting a response, even if it’s just for a small trial project.

5. End With a Friendly, Human Sign-Off

If anything, clients prefer when you are casual and relaxed with them. So, don’t overthink the ending. Just keep it warm, simple, and real.

Something like:

"If this sounds like what you're looking for, I’d be excited to help out. Appreciate you taking the time to read this."

That’s it. No stiff formalities, no robotic sign-offs. Clients are more likely to hire someone they like. So ditch the corporate tone and just sound like a real human being.

Bonus Tips

• Don’t send the same proposal to every job. Always personalize.
• Use their name if you can find it. Even if it’s just “Hi John,” it makes a difference.
• Keep it short. 150–200 words max. Your job is to earn a conversation, not dump your entire resume.
• Focus on value, not features. Instead of saying “I’m detail-oriented,” show what that means: “I once caught a $2,000 billing error that saved a client’s project.”

Conclusion

Upwork is competitive, especially when you’re starting out. But most freelancers are still sending the same bland, boring proposals that don’t speak to the client at all.

If you take the time to personalize, empathize, and focus on solving the client’s problem, you’ll instantly stand out.