5 Upwork Proposal Tips (+ Proven Upwork Proposal Samples) – Kings of Conversion

5 Upwork Proposal Tips (+ Proven Upwork Proposal Samples)

Looking for some quick Upwork proposal tips to help you get hired fast?

Check out these 5 Upwork proposal tips and get a free Upwork proposal sample below.

I needed help with a quick job the other day.

So I decided to post my first ever gig on…

(WAIT FOR IT!)

Upwork!

Yes! After the freelance copywriting challenge I hosted, I was kind of excited to experience the OTHER side of the hiring desk.

And so far, it’s been absolutely fascinating.

So today, I wanted to share some key Upwork proposal lessons and tips for applying to gigs based on what I’ve seen in the last 24 hours.

My goal with sharing this is that you’ll learn some powerful insights the next time you go applying for gigs… or just have fun reading along!

So let’s dive in!

Upwork Proposal Tip #1 – Remember, You Are One Among MANY

The first thing that shocked me was how fast applicants FLOODED my job posting.

In a matter of 24 hours, I had 24 proposals for this gig!

I don’t know if it’s just because of the category I posted in (contracts/law), but that’s A LOT to sift through.

Honestly, it was a bit overwhelming. That’s important because you need to understand how a potential client feels in order to properly pitch them.

They’re busy. They’re reading lots of pitches. So how can you stand out right away with a pitch that’s to the point?

The takeaway: Remember the saying, “if I had the time, I would have written a shorter letter.” It applies here A LOT.

Because imagine if I let this run another day, I’d probably have 40+ pitches to weed through, which is overwhelming to say the least.

So before you send your next proposal, put yourself in the mind of someone getting 30+ pitches. Ask what they’d like to see in a great proposal? How long would it be? What would the first words need to say to instantly stand out?

Upwork Proposal Tip #2 – Job Success Stands Out Like A Sore Thumb

The second big thing I noticed was how important the job success score was.

Not gonna lie…

It was probably the thing I caught my eye first.

For example, look at this applicant who only had a 71% success score.

Upwork proposal tips

I don’t know if it’s just my computer or the way that Upwork chooses to color in that line, but 71% looks AWFUL.

And I couldn’t ignore effect it had on my psychology. I was like, “this dude is totally going to screw this up if I hire him!”

So he was an instant nix.

Compare that to this applicant who had a 96% success score!

Upwork proposal tips

Just looking at that, I felt MUCH safer in potentially working with her.

The takeaway: Job success is CRITICAL. So even if you’re just doing small gigs (like the $25 blog post I wrote during the challenge), they do serve a purpose and help you with signaling! So don’t feel discouraged if you’re not signing the biggest gigs yet. I’d rather see you with a high 90s% success score than taking on big gigs early that don’t give you a perfect job success rating.

Upwork Proposal Tip #3 – Your First Words Are Everything

It’s crazy how much weight goes into those first few words in the proposal. Because as the client, it’s really all you can see.

So many people didn’t even take the time to do ANY level of personalization!

Like this one who wrote “Dear sir or madam”

Upwork proposal tips

My name is Rob. I signed the thing as Rob. He couldn’t at least say that!

These “first line mistakes” were instant turn offs.

The takeaway: Do not waste the space of the first few words. AND PLEASE do NOT send generic messages. Use that space to draw people in.

Upwork Proposal Tip #4 – Underbidding Is A Horrible Strategy (Unless You Give A Reason)

Dramatically underbidding a gig has WAY less effect than you might think.

For this job, I put the budget at $250.

So the vast majority of freelancers applied at exactly that rate.

Except this one who bid $150.

Upwork proposal tips

I think his plan was to catch my attention with a low fee.

But honestly, it had the opposite effect on me.

I was like, “Wait – WHY is this so cheap?”

(NOTE: if he’d addressed that in his proposal, it might have worked. But he didn’t. So it just seemed like I was going to get what I paid for and I avoided him.)

The takeaway: Don’t underbid a gig just to stand out … unless you’re willing to address that in your proposal. Especially for a fixed price gig. It just looks cheap! In fact, you might do better trying to go the other direction (more expensive) to stand out.

Upwork Proposal Tip #5 – A Few Words From The Job Posting (Mirrored Back) Go A Long Way

It was so refreshing to have someone apply to my job who clearly read my job posting.

Even a few words that related their expertise back to my gig went a long way.

This guy REALLY stood out to me despite the fact that he had $0 earnings and job history.

Upwork proposal tips

In my book, he’s the winner! Even above the people with more proof. Simply because it was clear he read it and wanted to help!

The takeaway: Personalization goes a LONG way. Please don’t spray and pray the same message over and over again. Take the 10 minutes it takes to adjust your pitch according to who will be receiving it.

Speaking of Upwork proposals…

Apparently the templates I shared with you all during the Upwork vs Cold Email challenge is working like CRAZY.

Want to see the script that helped this person land a $420 gig?

Learn more here.