Upwork Proposal Writing 101

Even if you’re not an aspiring freelancer, learning to write a good proposal (cover letter) is something that can help you at any stage of your career.
It teaches you how to write better, how to grab attention, how to sell yourself better to prospective clients, companies, or partnerships.

Although today’s article is focused on Upwork Proposal writing, I would invite you to read through and perhaps learn a thing or two about effective proposals that make you stand out from the red ocean of competition.

What you will learn here, you can apply elsewhere easily – be that your cover letters to job applications, pitches to potential investors, or just cold outreach on any networking platforms.

So let’s get to the meat of it.

How to write an effective Upwork Proposal or Cover Letter?

Before you start writing your proposal, you need to understand how your proposals appear to the end client. 

This is how you appear to the end client:

upwork proposals client view image

Now the key takeaway here from the perspective of proposal writing is the first 2 lines.

Yes, that is all that it takes to miss out on an opportunity – the first 2 lines of your proposal.

If you’re wondering what everything else is supposed to mean, I would request you to read the full Upwork Masterclass guide here.

Structuring your Upwork Proposal / Cover Letter

The base structure for any kind of proposal is usually similar, especially that is oriented at answering a requirement or job application.

1 – You lead with a strong and relevant Hook

2 – You add your best piece of portfolio in an accessible manner

3 – You introduce yourself in elevator pitch style (learn how here)

4 – You list out your relevant past work or portfolio

5 – You close out with an enticing CTA

If you’re writing a cover letter for a corporate job, you may get a bit more formal, but the core structure will remain the same.

That being said, let’s breakdown the most important aspects of an Upwork proposal.

How to Write Good Hooks For Any Proposal

So as you saw above, you have 2 lines to grab all the attention there is.

First thing you need to learn is to write good Hooks. 

What is a hook?
Anything that grabs attention – usually in a professional manner

My go to tip for writing good hooks is to learn about the common pain points within the industry of your particular skill set, understand what the clients hate, what the clients love, and use that to your advantage to grab attention.

For example, in PjM work, clients hate dealing with poor communicators, so if I see a job which requires good comms, I would lead with something such as:

“You’ll never have to follow up on pending work when I am there. Documentation, communication, and deeply understanding the problems at hand is what sets me apart.”

This covers a pain point that is common in these categories of gigs, it shows the top 3 skills I am adept at while linking it back to the role at hand.

Basically the gist is to say something in this format:

“Having worked with clients in [specific industry], I know what it takes to deliver results that exceed expectations [mention 1-2 expectations typically common in these kinds of jobs].”

Or

“With [X years] of experience in [specific skill], I bring a unique perspective that can help [insert the problem you will solve].”

Or

“I understand the challenges you’re facing with [specific issue]. Here’s how [Insert how you will overcome it].”

Must Have for an Upwork Proposal

If your hook worked, the client is in, now what?

They expect to learn about you – quickly.

What’s the most effective way to showcase yourself?
Add a video to your proposal.

A picture tells a thousand words, and a video shows what they mean. (patent pending)

Now I understand that recording a custom video for each new job application is basically impossible in most cases. But, you do need to make a habit of it for the jobs that really matter.

Custom videos catered around the client’s job application is the best way to convince the client that you are willing to go the extra mile, and work their pain points out.

The best way to record a video is this

1 – Open the client job application in a tab
2 – Open 4-5 tabs of relevant work you have done related to the specific job
Or
2 – Open 4-5 tabs of portfolio items that you have done related to your skillset
3 – Have a nice canva graphic with a CTA to end the video on – an image that says something like ‘Message me on Upwork to proceed’

Now open your favorite video recording app, mine is loom, and record 3-5 minutes just walking through everything.

Start with a short intro, don’t bother naming yourself, get to the point, walk through the job application and tie it to your past work or portfolio, and end on the CTA screen.


Looking for more helpful tools, guides, and templates?

Check out the SK NEXUS resources page.

These resources will help you if:

  • You are a Freelancer and want to transition to a Services Business
  • You are an Agency and want to provide better value to your customers
  • You are an employee looking to scale up
SK NEXUS resources, tools, and templates, cover image

How to close it off

With a strong Hook, and a good video – you’re 80% there to be honest.

The rest of the proposal can pretty much be a template, stating your short introduction, past work, key achievements – etc 

I highly recommend creating blocks of texts you can mix and match depending on the specific proposal. See this.

Once that is done, here is the last important bit – ending with a CTA.

A call to action is the most important part of the proposal after the client has viewed it. They need to be reminded that you are available and willing to work on the gig – right now.

Here’s an example:

Let’s schedule a quick 20 minute introduction call so that we can discuss the engagement in more detail. I work UK hours and am open 9AM GMT to 5PM GMT. 

Here are some more you can use:

1 – If this seems like a great opportunity, let’s connect today! Here’s how you can reach out:
Click the green Send a Message button.
Drop me a message and share any relevant details you think I should know.
Hit the green Schedule a Meeting button to pick a time for a Zoom call.

2 – To proceed, the best next step is to have a brief Zoom meeting to discuss the project and determine if we’re a good match. Just send me a message below, and we’ll arrange it!

3 – How about we schedule a quick call to discuss your needs? I can give you feedback on whether we’re a good fit after just a few minutes of conversation!

Try these out and see which perform better for your category of clients.

The main goal here is to remind the client you are available and willing to talk about next steps.
This shows your seriousness and commitment beyond just showing that you’re the right fit for the job.

What matters most in Upwork Proposals and Cover Letters?

Consistency and iteration.

Over the 2 years I have worked on Upwork, I have a living document with 25+ versions of the cover letter I have used and improved over time. That’s 15,000+ words for those who don’t get it.

Things change, trends change, but the fundamentals stay.
And you can only constantly improve if you constantly iterate.

Lemme know what are some of your favorite ways to write Upwork proposals? Email me at admin@sknexus.com


Getting value from SK NEXUS? The mission is to make knowledge accessible – We hope that you can share among like minded people.

Everything you see here – and more is powered by your Support. You can always pitch in by clicking the buttons below.