How to Write a Winning Upwork Proposal For VAs (Without Sounding Like Everyone Else)

If you’ve ever stared at a blinking cursor trying to write an Upwork proposal, you know how much pressure sits in those first two lines. You’ve got seconds to prove you understand the client, show your value, and sound human while competing with dozens of freelancers saying the same thing.

That’s why I created a simple, repeatable process for writing proposals that actually get read. It’s not about templates. It’s about clarity, empathy, and structure. This is the same system I teach inside my VA coaching program and the foundation behind the “How to Write a Winning Upwork Proposal” cheat sheet.

And remember, this is just one way. There isn’t one formula for success on Upwork. There are several ways to write a great proposal — this is simply a proven one that works.

1. Research the Client Before You Write a Single Word

Don’t rush to hit “Submit.” The real work happens before you start typing. Read the job post carefully, check the client’s reviews, and if possible, look at their website or LinkedIn.

You’re not just gathering facts. You’re uncovering their pain points. What problem are they really trying to solve? What’s missing or messy in their current setup? When you understand that, your proposal becomes a solution, not a sales pitch.

2. Position Yourself as the Answer (Not Another Applicant)

Clients don’t hire task-takers. They hire problem-solvers.
Translate your skills into outcomes. Instead of listing what you do, describe what your work changes.

For example:
Instead of saying “I manage inboxes,” say “I create communication systems so nothing slips through the cracks.”
That small shift changes how they perceive you from a virtual assistant to a strategic partner.

3. Start With a Hook That’s About Them

The first two lines make or break your proposal.
Skip the “I’m excited to apply” intro. Lead with a reflection of their goal or challenge:

“I saw your post about automating your client onboarding, and it’s a smart move. You’ll save hours every week once it’s streamlined.”

That opening tells the client: you get me. And that’s half the battle.

4. Build a Short, Strong Body

Keep it structured and simple:

• Show how you’d approach the project.

• Add one proof point (a quick result or story).

• End with a soft call to action (an invitation to connect).

You don’t need to oversell. You just need to sound like someone who’s thought it through.

5. Add a Proof Point

A quick client result or testimonial adds weight to your words.
It doesn’t have to be fancy — just real.

“I helped a client cut response times by 60% in their first month of outsourcing.”

That one line builds more trust than five sentences of adjectives.

6. Keep It Tight, Confident, and Human

Polish matters. A clear, warm tone will always outperform something over-rehearsed or robotic.
Keep your proposals under 250 words and make every sentence earn its place.

If you sound like someone they’d enjoy messaging, you’re halfway to hired.

Bonus Tip: Write Your Proposal Like a Post

Here’s where most freelancers miss the mark.

You need to start thinking about your Upwork proposals the same way you think about your content. You only have a few seconds to grab your potential client’s attention. If you’re not writing with a hook and a re-hook, your proposal will blend right into the crowd.

Think about the anatomy of a great LinkedIn post — a scroll-stopping hook, a short story, a bit of proof, and a clear takeaway or CTA. Your proposal should follow the same rhythm. That’s how you make a human connection before the client ever opens your portfolio.

When you write with flow, energy, and empathy, your proposal reads like something the client wants to reply to, not something they feel obligated to skim.

Final Thoughts

Writing great proposals isn’t about gaming Upwork’s algorithm. It’s about understanding people.

When you learn to translate a client’s needs into clear, confident language, everything changes — your response rate, your confidence, your income.

This framework is one way to do it. There are others. And I’ll be sharing them all because the glow up is for real.

So follow me for more tips, templates, and coaching insights that will help you write proposals that actually get clients excited to hit “Reply.”

Let’s glow!

— Monica #TheVAGodmother 🪄