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How to win Upwork: proposal writing

Regardless of how powerful your profile is or how many invites you get, the humble proposal will always be one of the most useful tools at your disposal on Upwork. You can spit out bids to as many jobs as you can afford, every single day. And with connects (Upwork’s currency) going for $0.15 apiece, and each job costing 2-8 connects, it’s one of the cheapest ways to acquire new work.

However, there’s a big problem:

Your proposals are boring, dude. Nobody wants to open them, and when they do open them, they don’t want to read them.


Because your entire proposal is about you. There’s nothing in it about the client. I know that because I’ve hired on Upwork before. The average proposal I received was 100-500 words, sometimes as many as 1,000, of the freelancer talking about their experience and their expertise.

This is especially bonkers given how many guides there are just like this one on writing great Upwork proposals. I’ve read a dozen of them at least, and you people don’t seem to be listening to the one common theme:

The proposal should be about the client.

You just can’t copy and paste the same version of YOUR life story to everybody and expect it to convert well. Your proposal needs to indicate, in the first two lines, that you’re writing specifically to (and about) the person who posted the job.

How proposals appear on the Upwork client dashboard

Make no mistake, I understand that some clients write remarkably lazy job postings with no details about them at all. But that doesn’t matter as much as you think it does.

Even if you know nothing about the person who posted the job or their business, you’re better off making assumptions and speaking to a specific person—even an imaginary one—than talking about yourself endlessly.

For example, let’s take a look at the proposal structure I used this month to close a $9,000 job:

A winning proposal formula

Here’s the job I applied to:

“I am looking for someone to help me develop an aircraft market place. This online market place will allow users to post aircraft on the site for a fee.”

That’s it. Pretty succinct.

The client had no reviews, had not hired before, and didn’t even have a payment method verified. His job posting had no set budget, but said he was looking for expert level freelancers.

Here’s the proposal I submitted:

The proposal

“WOW. Very glad I caught this. If you’re looking to build the next Trade-a-plane or Barnstormers, then I’m the perfect guy for this job. Here’s why:

  1. I’ve built two similar listing sites recently. One is pay-per-lead where the lister pays to contact applicants. See it here: [URL]

    The other is pay-to-list, similar to what you required. (Note: It’s basically a freelance marketplace like Upwork—it has a commission structure as well as a pay-to-list structure). See it here: [URL]
  2. I’m 12 hours into my private pilot certificate and am familiar with the industry. I know exactly how to design and build you a solid alternative to Trade-a-plane or Barnstormers.

Check out some of my other work at my website. If you’re interested in talking more, hit reply and let’s get acquainted.


[my portfolio URL]

Why it worked

Definitely not the best-written proposal you’ve ever read, right? And yet it still closed the job. Let’s look at the structure I used.

First of all, it had a clear hook at the beginning.

Aircraft listing websites are very well-known in the aviation niche, and so starting by listing a couple of the big names did a lot to set me apart from the other freelancers on the job dashboard. The client instantly knew that I was familiar with his industry, and that led him to click into the proposal.

Second, I made a promise. It wasn’t a great one, but it was still a bold statement: “I’m the best guy for the job.”

Third, I showed similar work that matched the technical requirements he had. Even though the examples I showed weren’t specific to his industry, it still demonstrated my technical proficiency. This proof was the most important part of the proposal.

Finally, I ended it with a call to action. It wasn’t even a very good one, but it still did the trick: “Hit reply and let’s get acquainted.”

This is the system I use on my proposals, and it works.

The formula

  1. Hook
  2. Promise
  3. Proof
  4. Next Steps


“WOW. Very glad I caught this. If you’re looking to build the next Trade-a-plane or Barnstormers…”

Start with a hook that sets you apart from the competition and indicates that you know what you’re talking about. Pattern interrupts work great here. If you can start your proposal with something that stands out from the crowd, you’ll get more attention and win more often.

But attention is only part of the hook. It also needs to show your client that you have the knowledge and skills to solve their problem.


“… then I’m the perfect guy for this job.”

Put it in plain writing that you’re able to do the job. Show self-confidence. If you hedge or indicate uncertainty here, your client will smell it and will be rightly repulsed.

Again, my promise here was weak. I didn’t promise any specific results or outcomes—I just said I was the perfect guy for the job. Granted, I didn’t have much to go on with the limited info available in the job posting.

But usually, you’ll have more information to work with. When you write your promises, mention the specific outcomes your client either specified or hinted at in their job posting.


“Here’s why:”

Master salespeople close on proof. Don’t just say you’re the best man for the job. Show why. Display examples of your work that match the job posting’s specifications, and cite the positive results that you earned for your clients.

If there are any other accolades you have that are relevant to your client’sneeds/situation (not just accolades that you’re proud of), mention those as well.

Further: “Here’s why” was in the first two lines and was visible on the job dashboard. By hinting at valuable information that’s available inside the proposal, I opened a story loop that could only be closed by clicking in.

Everything from “here’s why” to the call to action at the end was straight proof. This should be the bulk of your proposal.

Next steps

“Hit reply and let’s get acquainted.”

The purpose of the cover letter is not to sell the job. It’s not even to sell the meeting.

The purpose of the cover letter is only to sell the opening of a dialogue. Prompt your client to take the next step—in this case, just replying to you.

Some tips

First of all, using a framework like this doesn’t mean copying and pasting. It means WRITING according to the framework.

Write all your proposals from scratch, keeping the steps of this framework in mind. If your proposals are copied and pasted, your clients will be able to tell, and you will attract significantly less attention.

Even if you don’t copy and paste, you’ll attract less attention if your clients think you did. So make sure that your proposals are clearly written for the person they’re intended for.

Further, there is no one-size-fits-all approach to proposal writing. The things that work for my offer and my niche might not work for yours.

With that in mind, spend a month or two experimenting with your system for sending proposals. Do things the same way and tweak one factor at a time to see what works and what doesn’t.

Send a consistent number of proposals per day. The number of proposals you send is the fuel you put into the engine. More fuel will rev the engine higher, but it won’t make it any more or less efficient.

If you’re flat broke and need work now, send around 10 a day if you can. If you’re not desperate for work, send 2-5 per day.

Experiment with the right time to send proposals. Try doing it early in the morning, mid-morning, early afternoon, late afternoon, and evening (for a week each). Depending on who you’re competing against, you’ll get different results.

For example, if you’re bidding on US-only jobs, you’re pretty much competing only with people within 3 hours of your location. You might have good luck catching clients in the evening in this case while your competition is relaxing.

If you’re bidding on worldwide jobs, you’re bidding against dirt-cheap freelancers in countries where the US dollar has serious purchasing power. Try submitting proposals during the day when many of these freelancers are snoozing.

Faster is almost always better. I don’t know the data, but in my experience, the majority of Upwork “clients” are window shopping. They put up a proposal, check out the prices, and never hire anybody. Sometimes they don’t even look at the job after they post it.

In any case, you have the best shot at being seen by the client if you respond within the first hour (before they have a chance to forget about their job post).

Next, length. Keep your proposals short. Your clients will often have at least 20, sometimes a hundred or even more proposals to review. If yours looks intimidating, wordy, boring or time-consuming, they’ll find any reason they can to skip it. The proposals I send that turn into jobs are almost always under 150 words.

Finally, let’s talk about boosted proposals. In my experience, the boost is a profound waste of money. I’ve never won a boosted job, and I only see a 10-20% increase in views on boosted proposals. Many of the jobs I boost end up being clients who never look at their posting again, so I might just be very unlucky. But in my opinion, it’s a total waste of your money.


Nobody likes a boring proposal. This is good news for you, because pretty much everybody’s proposals are boring. Despite all the great information available on writing great proposals, it’s still very easy for you to stand out.

Here’s how:

Make your proposal about the client, not about you. The only information you share about yourself should be directly related to the client accomplishing their mission.

Follow a four-piece framework:

  1. Hook (pattern interrupt, story loop)
  2. Promise (specific = strong)
  3. Proof (bulk of the proposal)
  4. Next steps (usually a reply)

Write your proposals on the fly with that framework in mind. DO NOT write one and then copy and paste it. I’m serious, just don’t do it.

Write 2-10 proposals a day. Tweak different factors one at a time to find what works best for you. Keep your proposals short, don’t boost them unless you really want to, and put a higher priority on the most recently posted jobs as they’ll maximize the odds of your proposal being seen.

There are bottom-of-the-barrel clients on Upwork, make no mistake. But there are dream clients to be had there too. You might have to put in some extra work to find them, but it’s worth it.

Have a killer week my friend. Now get out there—your dream clients are looking for you right now. Make sure they find you.


I'm John Kakuk.

I’m a brand designer, web developer and marketer working with architects, engineers and construction companies. My purpose is to help others achieve the best versions of their businesses and themselves.

Here's how I can help you: