How to Submit an Upwork Proposal the Right Way

freelance connection Sep 03, 2021

Welcome to this week’s episode of the Freelance Connection! I wanted to take some time to share some of my thoughts and best practices about the whole job search process on Upwork - from searching the jobs, to finding jobs you’re interested in, to sending proposals. This is something that is top of mind for me right now as I’m in the process of hiring for myself, and I’m also helping a couple of clients hire, so I'm going to give you my unique perspective from the viewpoint of both the freelancer and the employer.

As a freelancer, when I'm searching for jobs, I always carve out time to look through the jobs. I want to make sure I’m aligned with them and that I can be successful in that role before I spend the time applying.

My process goes something like this: I always start by scrolling through all the postings and “hearting” the ones that I would like to apply to later. Next, I go back and take a closer look at the jobs that I saved. When I do this I'm looking for these three things:

  1. Is this something I'm genuinely interested in?
  2. Does this look like a good client?
  3. Is it in the pay range that I’m looking for?

When everything comes together, and I've decided to apply for the job, I have time invested. I've found it in the Upwork job search, I've went back a second time and read it thoroughly, and now I'm ready to apply.

Make the cover letter the star

Once I've decided to apply for the job, I put more effort into the actual application process. When I’m submitting my cover letter with my proposal I’m making sure to include everything, because in general people don’t look at your profile at this point. They’re looking at what’s directly in front of them, and that’s your cover letter. Don't be  afraid to repeat things that are on your profile in your cover letter, because if you don't hook them right now, chances are they are never going to look at your profile anyway. After sifting through more than fifty cover letters between my open jobs and those of the clients' I'm hiring for, I can say this from experience.

The average cover letter I've reviewed is about 4 to 6 sentences. If I only get 4 to 6 sentences, and you haven't hooked me, chances are I'm going to archive that cover letter, and other potential employers probably will, too. I'm not going to put my time into looking at their profiles, because they didn't put any effort into their proposal. So, if you're doing this, you're just not being seen. Although your profile is your calling card, your cover letter is intended to be that correlation or that hook that is going to intrigue that potential client to set you apart from every other person that is applying for that job. Take a minute to think about it. How are you doing that?

So what goes into a good proposal?

Here’s an outline of what I include in my proposals: 

  1. A hook in the first 3 to 4 sentences. I pick something out from that specific job posting that I can go in-depth on.
  2. Brief highlights about me letting them know who I am, what I’m about, what I do, what services I offer, and what my availability is.
  3. I let them know what it looks like to work with me. This explains what my work style is and sets the stage for me to take a little more control of the communication and of the boundaries.

You are in the driver seat of your proposal, but you also have to be aware that you’re matching the skills needed in the job listing. And, it’s totally okay to ask additional questions! For example, sometimes when I’m applying for a job I see extra questions that are just not relevant at all. In these cases I reply, “Hey, I’m not sure on the direction that you want me to answer this question. I would love to discuss this in person.” Or if it’s a general enough question I might include a little bit of strategy, followed by, "I would love to connect on a call." Every time my goal is to connect with them on a call. This also gives them a clear picture of what the next steps are with me, and that’s to book the call so we can discuss the overall scope of the project.

What I’m really trying to drive home is to make sure you’re spending extra time on those proposals. Pick up on the little details in the proposal that are placed there strategically for you to address. After being on the hiring end multiple times now, I realize that when I'm getting anywhere from 30 to 40 job proposals, I’m not going to schedule 30 to 40 calls. I’m going to schedule calls with the top 3 to 4 people that show effort by paying attention to the details. This shows me that they’re really interested in my job listing when they submit their proposal. 

If you have any questions or comments on this episode of Freelance Connection, please send them over. I want to continue the conversation, because this is really heavy on my heart right now and I want everyone to be successful.

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