How To Write An Upwork Proposal That Lands You The Job In 2020

Upwork is a go-to source for people who are looking to make their first dollar online.

As the largest freelance marketplace on the web, the site has opportunities for everyone. 

In fact, it’s actually how I made my first real money online. My first job was a copywriting job that paid $50 for what was close to 10 hours of work. I was the second person the client had paid. It was only thanks to a little begging — and way underpricing my competition — that the client agreed to give me a shot. 

Over the next few years, that job paved the way for many more. And more importantly, with more experience, I was able to spot niches where the supply of quality freelances hadn’t caught up to demand. 

In my case, that was landing page copywriting and design. 

As I continuously increased my rates, long gone were the days that I had to underprice my skills to win clients. In fact, at $150 per hour, I had the highest hourly rate in my niche.

The fact is that many people fail in making real money on Upwork. They sign up, apply for a few jobs, then quit after not getting hired.

The marketplace is no doubt competitive, but you can’t deny the fact that there are many freelancers making very good money on the site. And just like you, they had to start from scratch. 

Being successful on Upwork starts with understanding how to write quality job proposals. Yes, you’ll want to deliver great work. But in order to land the best jobs, you’ll also need to learn how to write the best proposals. 

As someone who has both worked and hired extensively on Upwork, I’ve seen just about every Upwork proposal mistake imaginable. And yes, I made a lot of them myself. But over time, I developed a simple framework for writing proposals that have a high close rate on high-paying contracts. 

Today I want to share that framework with you.  

Common Upwork Proposal Mistakes

Before we get to that framework, let’s cover the common mistakes freelancers make when it comes to Upwork proposals. These are what you absolutely must avoid to become a high earner on the site.

It’s Not A Numbers Game

The common thought process among beginners is that the more jobs you apply for, the more of them you’ll land, and thus the more money you’ll make. 

But in my experience, that’s the wrong mindset to have. 

It’s much better to take a “sniper” approach. You’re not just trying to land a job, you’re trying to land a great job. And, chances are, if you just blast out proposal after proposal, looking to get lucky, that’s not going to lead to great jobs. 

Pro Tip: Think of unique keywords that apply to your skillset. Be creative here because you’ll want to input these keywords into your saved searches, which will provide you a feed of opportunities. 

For myself, I saved searches for terms like CFP and insurance marketing — topics in which I had practical professional experience. However, I also used terms like Unbounce, a landing page software I was proficient in. In addition, at times I would input the names of various marketing experts who I was familiar with. One of my higher paying jobs came from a saved search with the name Jeff Walker, who created a popular marketing funnel that I had experience with.

Sending The Exact Same Template To Everyone

The next big mistake you want to avoid is sending the exact same proposal to everyone. When potential clients get your proposal, they’ll see first an abbreviated version of your cover letter.

When I’m hiring on Upwork, templates are easy to spot and quickly deleted. Unfortunately, there is no winning template you can just copy and paste into every proposal — although many people still try. 

Pro Tip: Address your clients by their first name in your cover letter, which you can find in their Upwork client profile, so they know you’ve done some research. 

Trying To Close In The First Communication

Every job I’ve won on Upwork has required more than a simple cover letter. There was always a second stage, which included a chat on the phone, a video interview through Skype, or expanded conversations via email with the client. Actually, as you’ll learn, this is what you want to push for in your cover letter — a chance to communicate more closely with the client.  

The person who understands the client’s situation the best will most likely win the job, and often that requires more than reading their proposal.

Pro Tip: Leave your contact information in your cover letter. I included my Skype ID and cell phone number, making sure to mention that they could text me at either to set up a time to chat or ask any questions they have. 

Three Things You’re Looking To Do With Your Upwork Job Proposal

With the common mistakes out of the way, let’s look at what it is you’re actually trying to accomplish with an Upwork proposal. Yes, the goal is to land the job. But what needs to be done in order to accomplish that goal?

#1. Show Them That You Understand Their Objective

Your job is not only to uncover what the deliverable is, but also the underlying reasons why they’re posting the job in the first place. As such, show your potential client that you can not only get the job done, but that you can also minimize their time involved. 

For example, say you’re a freelance writer and the deliverable the client is looking for is a 1,000-word article. In your proposal, you want to mention that you understand what the end result is for them. However, it’s also your job to dig a little deeper and understand why the client wants that article. 

One thing you can be almost certain of is that the client wants to save time. As such, you might want to say something in your proposal along the lines of: “This is an area I have a lot of expertise in, so there would be minimal, if any, editing on your end to get the article published.”

#2. Provide Proof That You Can Get The Job Done

Most job proposals get dozens of applications. From the client’s perspective, how should they decide who gets the job?

Most clients are not looking to go through an extensive interview process, such as they would if they were hiring a full-time employee. Instead, they’re using factors like the Upwork Job Success Score to filter through the applications. 

From there, they’re taking a look at your cover letter, making sure you understand what they need. 

What’s next? Clients want to know you can get the job done right. And the best way for you to convince them you can is to show them proof. 

The good news is that you can get creative with your forms of proof. 

At times, I’ve directed the client to testimonials about my work on similar projects in my cover letter. Other times, I’ve linked to articles where I was featured as an expert. Most often, I would send them to a completed project of my own that was closely related to their job proposal. I’d accomplish this either by linking them to a portfolio sample or the URL where the work was published. 

Beginner Tip: If you’re an absolute beginner and don’t have a related work sample, create one! Be open with the potential client that you created this sample for your portfolio and that it wasn’t used for a client project. This shows initiative on your end, which clients always like to see. 

#3. Get Them To Continue The Conversation

As mentioned, the mistake is often trying to close the client in one fell swoop. Think of a job application for a full-time position; you wouldn’t expect to get hired after just sending in your resume and cover letter. The next step is always an interview. 

And while most Upwork jobs are not going to require you to do a formal interview, there will almost always be at least one follow up conversation before a decision to hire is made. So it’s your job to make sure that follow up happens. 

As a best practice, you’ll want to include your contact information. However, the best thing to do is to ask the client a question yourself. Even better, in your question, show your client that you understand their needs.

For example, a lot of the work I did on Upwork was combined copywriting and website design. So, I might say something in my proposal like, “It sounds like the type of landing page you’re looking for is very similar to EXAMPLE.COM. I really like how EXAMPLE.com does A, B, and C well. Is this what you had in mind?”

Because a lot of clients are looking to save time, they often hire the first person that is competent enough to get the job done. So, ask them a question that demonstrates your competence and then quickly follow up when they respond. 

Pro Tip: Enable desktop alerts and download the Upwork mobile app so that you can respond to client messages as quickly as possible. 

Proven Upwork Proposal Template

With the foundational knowledge from above, it’s now much easier to put together a repeatable Upwork proposal template that gives you a great shot at landing high-paying jobs. 

This template will involve four parts:

1. Personalized introduction
2. Demonstrate you understand their objective
3. Give them proof
4. Continue the conversation

If you’re brand new to Upwork, you’ll also want to make sure to create a professional looking profile, which I detail in this guide about getting your first job on Upwork. 

Step #1: Personalized Introduction

Here you’ll want to address the client by name and prove to them that you’ve thoroughly read their proposal. 

Example: Hi R.J., I saw that you were looking for someone who can write and design high-converting landing pages on the Unbounce platform. 

Step #2: Demonstrate You Understand Their Objective

Show them that you understand what they’re looking for, which includes both the main deliverable and other benefits (such as saving them time or making them money).

Example: I really think we’re a great match here. I’ve included a few work samples below, but since this is an area I specialize in, I could also offer a quick turnaround.

Step #3: Give Them Proof

Show them proof that you can get the job done. You can link to a live URL, such as your personal website or a portfolio sample on Upwork. 

If you don’t have a prior deliverable to show — for example, because you’re working as a virtual assistant managing someone’s calendar and email inbox — talk about your job experience. 

Example: Actually, I just finished up a very related project here on Upwork. Here’s a link to that project: Example.com. In addition, I’m happy to say that the client was quite satisfied with the results. Here’s the feedback they left: “Quote feedback here.”

Step #4: Continue The Conversation

Encourage the client to continue the conversation. 

Final Thoughts On Upwork Proposals

Freelancing on Upwork is an ideal place to get started making money online. In my case, the skills I learned on Upwork writing and designing were then used to build The Ways To Wealth, which I now run full-time. 

Upwork allowed me the space to sharpen these skills, and get paid for doing so. In addition, it allowed me to build up my emergency fund to take the leap to full-time blogging. 

So, in a sense, Upwork is a good gateway for those looking for a career outside of a traditional 9 to 5 job. You’ll quickly learn new skills, make money while doing so, and have a great understanding of business opportunities where there isn’t enough supply to meet the demand.