How to write “Moneyball” Upwork proposals: A counterintuitive way to win jobs with less effort

Written By Steven Alexander Young
June 21, 2022

In this post, I’m going to teach you the strategy I use for writing Upwork proposals – the exact same one that lands me jobs at $999/hr:

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 Obligatory proof that clients actually pay me that much

 Most advice for Upwork proposals falls into one of two extremes:

  1. Compete on volume: Some people say Upwork is a numbers game, so just send more proposals – one of them is bound to win a job (eventually). Google “best cover letter template”, copy/paste it to 100 clients every day, and cross your fingers.
  2. Compete on effort: On the other hand, some people say you should spend hours applying to each job, carefully crafting a 10,000 word personalized proposal – or even better, recording a custom new video proposal for each client!

The first never works, and the second makes the whole experience so time-consuming and miserable that it’s never worth it.

My proposals are something entirely different.

I call them “Moneyball Proposals”, and by the end of this post they’ll be a part of your arsenal too.

You’ll get to see me rewrite a real proposal using this strategy. Plus, I’ll show you how it helps even if the client doesn’t hire you, thanks to the way Upwork is built.

Let’s get started:

Why Upwork proposals are so unfair

Ok, I know how it sounds – but “Moneyball” isn’t some pyramid scheme hype word I made up.

It’s inspired by one of my favorite underdog stories ever, told in the bestselling book: Moneyball: The art of winning an unfair game (also adapted into a great movie).

I don’t actually follow any sports at all, but this book really struck a chord with me.

Baseball is said to be “unfair” because each team has a different budget for hiring. Unsurprisingly, the wealthiest teams are able to outspend their smaller competition to snap up all the best players.

But the book Moneyball tells the true story of how one unsuccessful baseball team – the Oakland A’s – found a way to start winning despite having one of the smallest budgets in the league.

Upwork can also feel like an unfair game – Freelancers may get equal opportunity to send proposals, but some applicants just have way more credentials and work history.

The hard truth is: If you write the same kinds of proposals as everyone else, those more experienced competitors will always win.

But there’s a different way to do things…

How the “Moneyball Strategy” works

20 years ago, baseball teams scouted players based on various criteria like running, throwing, hitting, etc. combined with less objective things like “Does their form look good?” or even “Does their girlfriend look ugly?” (which supposedly signaled a lack of confidence 🙄).

The way the Oakland A’s built a winning team was simple, but genius:

First, they laser-focused their scouting approach on the ONE thing that truly mattered:

“Could the player get on base?”

Then from those players, they grabbed all the ones who looked terrible by traditional standards.

The Oakland A’s knew that things like strange throwing form (or an ugly girlfriend) made no difference if a player met their #1 criteria – but the worse these players looked to scouts on other teams, the cheaper they were to hire.

To everyone’s surprise…

These bargain-rate players were competitive with wealthier teams filled with “traditionally-good” superstars.

And despite their tiny budget, they achieved a record-breaking 20-game win streak!

The ONE thing all your Upwork proposals need to do

To write an effective Moneyball proposal, you want to double down on the one thing that truly matters for winning a job – and make sure you don’t waste your “time budget” on anything else.

It’s as simple as that… but most freelancers get tripped up here.

When I look at proposals from people I’m coaching, almost all of them fall into the same mental trap:

They assume the point of a proposal is to instantly get them hired.

In the worst cases, some freelancers fill their proposals with all sorts of bloat:

  • Information on their background and experience
  • A description of how they’ll do the job
  • Their proposed pricing terms
  • When they can get started
  • A suggested deadline
  • Maybe even more, like cancellation terms or number of revisions included

This is a TON of weight for one message to carry. Not to mention, a ton of extra work to put together, making each proposal feel like a slog to write.

On the other hand, there are freelancers who try to fill their proposals with “persuasion tactics” like faking mentioning how busy you are (which clients can always see through). Relying on these won’t help you either.

With your Moneyball proposals, you’re going to slash all of that dead weight and focus on a very different goal:

Getting a reply.

I’ll say it again:

The only job of your proposal should be to get a reply.

Let me explain…

Proposals that sell too soon make you miss out

If a client reads your proposal and messages you back, your chances of winning a job skyrocket in several different ways, most of which you’ve probably never considered (lots more on this in a second).

But for starters, continuing the discussion beyond your initial proposal lets you:

  • Build rapport with the client
  • Get behind-the-scenes info about what they really care about
  • Clarify requirements to help you price better
  • Educate the client on what they should really be looking for
  • Address all of the client’s actual objections, as they come up
  • and much more, depending on where the conversation goes!

All of these are real, tangible advantages which help you sell yourself WAAAY better than you possibly could in one blind message. Meanwhile, your competitors only have what’s in the public job description to work with (which is rarely enough).

Of course, getting a reply doesn’t guarantee that you’ll actually win the job (which is obviously your end goal). But you need to let go of the idea that it’s your proposal’s job to get you hired instantly.

A good Moneyball proposal is one that deliberately sacrifices all the salesy components for a higher chance at starting a back-and-forth conversation, even if it means you’ll never get hired on the spot.

This lets you write much shorter proposals way faster – without sacrificing any personalization. Then, you’ll only put in the effort to sell when you a) have an information advantage over your competitors, and b) know that the client is ready to be sold.

Time is money for freelancers, and this saves you TONS of it.

How To Get Replies To Your Upwork Proposals

Ok, so how do you actually get those replies?

My favorite way is to end my proposal’s cover letter with a simple question about the job details.

This gives the client a specific action step, making it easier for them to follow through.

It takes much less brainpower to respond to a direct question than to formulate a reply to typical closing lines like “Hope to hear back soon”, “Let me know if you have any questions”, or worst of all: “I look forward to working with you”.

The concept of asking a question isn’t anything groundbreaking, and other blogs have tried to give this advice before.

The problem is, the way they execute is always a little “off” because they don’t understand the full psychology behind it.

For best results, there are a few simple rules you want to keep in mind:

1) Do NOT ask too many questions

Even if there are a dozen questions you want the answers to, don’t try to cram them all in your proposal. The goal is to make responding as EASY as humanly possible. Asking a question every other sentence or linking to a long survey will make replying to you feel like a chore. You can always ask additional follow up questions later, so try to stick to just one in your initial proposal.

2) Do NOT ask questions that are too tough

You don’t want your one question to be too daunting to answer either. For example: One blog post I saw tells freelancers to ask a question like “I have a couple more ideas I could share as well. When is the best time for us to connect this week?” This may seem innocuous, but replying requires the client to check their calendar and commit to scheduling something. That’s way more effort for them than if you asked something factual about the job that they could answer off the top of their head. If you still want a call, you can always do that later on when you have better chances.

3) DO make your question the last thing

If you ask your question at the very beginning of the proposal, clients are going to forget it’s there. They most likely are sifting through dozens of proposals. Make their lives easy and put your question at the very end so they can immediately answer it without having to scroll back up.

Example of an actual Moneyball Proposal

The following is a real proposal I found on another blog that only gets halfway there. That blog post does suggest asking a question to get replies, but the result isn’t as effective as it could be:



Thanks for the job invite. It’s a pleasure to meet you. Can you please tell me more about your cloud based products and services? Also, can you send me a link to your site? What web platform are you using for your site? Do you have a monthly budget in mind for PPC advertising?

I am google adwords search certified. I have done adwords work for clients from all over the world in a variety of industries including the following: hospitality, marketing, real estate, retail, and tech.

Best regards,


They use this as an example of a well-written proposal since the freelancer won the job, but that doesn’t mean that it can’t be improved (and them winning the job probably had more to do with the fact that they got an invite from the client).

You’ll see that this proposal breaks all 3 of the rules I gave above:

First, they ask four different questions. Sending a reply to this freelancer requires the client to complete the equivalent of a small survey.

Second, the questions aren’t particularly easy to answer either. The first one in particular is extremely open-ended and presumably would require a several-sentence response.

Finally, the questions are all asked at the beginning of the proposal rather than at the end. Now, I doubt any client will think “Ugh I’m too lazy to look at the last paragraph to see what those questions were… guess I just won’t hire this person!”. But this DOES add unnecessary friction, and every little bit adds up.

Here’s how I might have edited this proposal with the following limitations:

  1. I don’t know what the actual job post said, so I’m going to assume it was super vague.
  2. I don’t know the freelancer’s skills and background, so I’m not going to add anything that might not have been true.
  3. I’m going to stay as close to the original proposal as possible, since I want to focus on composition rather than writing style.

Here it is:

Hello ___

Thanks for the job invite. It’s a pleasure to meet you.

Whatever industry your business is in, I’m confident I can help – I’m google adwords search certified and have done adwords work for clients from all over the world, including hospitality, marketing, real estate, retail, and tech.

There’s one key question I have before moving on: Do you have a monthly budget in mind for PPC advertising, or are you looking for suggestions on that?

Best regards,


It’s very similar to the original, but this will be MUCH easier for a client to reply to.

Just imagine this proposal comes in when they’re sitting in an Uber ride that’s about to end, or they’re bored in a Zoom meeting where their attention is split. Chances are now much higher that they can reply right away instead of putting it off for later.

Note that I used only one of the four questions and made it even easier to answer by giving an “out”. If the client has no idea what their monthly ad spend should be, they can still reply with something quick like “I’m not sure, please let me know your suggestion”.

Some clients are talkative, and will reply to your single question with a several paragraphs long story of their life and all the details of their business and why it’s so cool. That’s always great – more material to use to your advantage in follow-up messages.

But even if they don’t, their one single answer opens the door for a bigger conversation. In the next message, this freelancer can use this “exclusive info” (that other freelancers won’t see in the job description) to better sell themselves, or just ask the remainder of their questions if they need more info. Either way, it moves them closer to a sale.

A real sample of one of my own Upwork proposals

So, this would be the perfect place to show you an actual example of a Moneyball proposal that I wrote for myself.


I don’t want to show that here. At least not yet.

Before I publish that here on the blog for any random person to see, I’m going to share them with my loyal subscribers first.

If you’re not subscribed to my email newsletter, it’s free to join.

You’ll not only be the first to know when I publish new stuff, you’ll also get access to the things I want to keep a little more exclusive (like examples of my own proposals).

Just sign up here:


Otherwise, maybe you can refresh this page every day and see if it updates… but don’t hold your breath.

3 More “Secret Benefits” from Moneyball Proposals

Ok, so we’ve already gone over how starting a 2-way conversation helps you get “secret” intel your competitors don’t have, making it much easier to sell yourself.

But there are other, less-obvious benefits to writing Moneyball proposals that make them even more effective:

1) “Interviews” scare away your competition

When a client replies to your proposal, you are now considered to be in the “Interviewing” stage.

This happens to be one of the things Upwork displays on job postings. Here’s how it looks:

Even if all the client did was answer your clarifying question, their reply will update the job posting to show all other freelancers that there’s at least one person being “interviewed”.

This has a HUGE demoralizing effect on other freelancers.

When your competition sees that the client is already “interviewing” someone (and maybe multiple people), they may wonder if they’re too late to have a shot. If they’re trying to budget their time, they’ll probably decide to just move on and find a less contested job to apply to.

A drop in new applicants also speeds up the hiring process – a steady stream of new proposals will make clients wait and see what else they get, but a sudden drop will push them to just decide on someone already.

You really shouldn’t obsess over how many competitors you have, but less competition obviously means higher chances of winning the job!

And that’s not all:

The Moneyball strategy has benefits even if you DON’T win the job…

2) Upwork pays you for each reply

For anyone who hasn’t sent their first proposal yet, “Connects” are the tickets you need to apply to jobs. It’s basically a system to stop freelancers from mass spamming copy/paste proposals to every job they see.

Each job costs between 1-6 Connects, and you only get a limited number of free ones each month before you have to pay money to get more.

But there’s another way to get more Connects…

Every time you get to the “Interview” stage, Upwork will reward you with 10 Connects!

With a high enough response rate, you can hypothetically send an infinite number of proposals without ever running out.

Yes, even if the client replies with “I hate this proposal and would never hire you”, you still win Connects to apply to more jobs.

This client scoffed at my quote… but I still got the Connects!

… just make sure that’s not the only thing you’re hearing 😅

Finally, what’s arguably the most valuable benefit of all:

3) Upwork’s algorithms turn replies into invites

Getting more interviews boost your interview stats (which Upwork not only tracks, but openly displays on your “My Stats” page).

Here’s how that looks:

With a higher-than-average interview rate, their algorithm will consider you to be more potentially hirable (even if other stats like your hire rate aren’t quite there yet).

That leads to showing your profile in more searches and suggestions, which means more clients will send you job invitations.

Needless to say, you have a much higher chance of winning a job if the client is inviting you to apply.

Most new freelancers won’t have enough of a work history for Upwork to suggest their profile very often. But getting a lot of responses will really help get the ball rolling.

“But what if everyone on Upwork starts using Moneyball proposals?”

After the Oakland A’s won their 20-game win streak back in 2002, all the other teams started using the same strategy.

The Red Sox tried to hire the Oakland A’s manager, offering the highest ever manager salary of the time – and they won the World Series just 2 years later by copying his strategy, even though he declined.

Once everyone knew this “secret” winning strategy, it ceased to be an advantage and just became the new way of playing.

But lucky for you, Upwork is a different story.

I can see whenever I post jobs as a client. The vast majority of proposals I get are absolutely terrible.

Even publishing this free blog post won’t change that. For years I wrote about Upwork strategies (ghostwritten for other peoples’ blogs and courses), but only a small fraction of people put in the effort to read, and even fewer actually implement anything.

Just having read this article means you have a huge advantage over everyone else.

And this is just the tip of the iceberg. If you want even more of an advantage, make sure to subscribe to my newsletter for the material I don’t release on the blog.

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