How Do You Win Independent Contractor Jobs on Upwork?

Almost everyone here has heard of Upwork; most reading this probably use it.

With Upwork’s community of freelancers rising by the day, it might seem impossible to win independent contractor jobs easily. 

How Do You Win Independent Contractor Jobs on Upwork?

There will always be competition in the world of business; the trick is to be better than your competitors. 

I’m here to tell you it’s not – and even better, this article will tell you exactly how to win your first independent contractor job on Upwork.

What is Upwork?

Upwork is the world’s largest online freelance marketplace—the service pairs freelancers of various expertise with clients across the globe. Within a few simple clicks, you can apply for projects, reply to potential clients, and create custom projects for clients to purchase. 

It can seem daunting at first. Imagine it: You versus a million other freelancers, all bidding for the same job worth $15. Okay, not quite. 

Don’t be put off by this. There will always be competition in the world of business; the trick is to be better than your competitors. 

Giving up at the first hurdle will guarantee failure, and ‘failure’ is a gross noun we won’t use for the remainder of this article. 

Project Description or Guideline Goldmine?

An example of an independent contractor job on Upwork.

The independent contractor job description is one of the essential features of a job posting on Upwork.

Why? It’s the bread-and-butter of an advert that can include everything you need to know before drafting your proposal. 

One thing to keep in mind is that clients will know when you’ve not read the description.

Besides questions and requests, you may have missed a client’s specification to include a particular word in the proposal. This is because they want freelancers who can pay attention and follow instructions – not ones who bombard them with irrelevant portfolio examples

Let’s take a look at an example of an independent contractor job on Upwork. 

  • The Title: It’s normal for clients to include the category of expertise they need (for example, SEO writing or proofreading). But, they may just outright tell you what they want. Project titles are usually simple, so you may need to dig deeper before starting your proposal. 
  • Expertise Level: When posting an ad, clients have the opportunity to specify whether they want beginner, intermediate, or expert freelancers. Be realistic here. If you have years of experience and a complete portfolio, you’re more likely to qualify for expert jobs. Likewise, new freelancers should stick to beginner projects to build their reputation and testimonials. 
  • The Description: This section of the ad should include everything you need to know about the project. You’ll want to make sure you directly answer any questions in the project description. It’s good practice to include relevant examples with your proposal. If you don’t have any examples to send, try explaining why you’re suited to this project based on a previous project. Be confident about your past work – you’re here to sell yourself. 
  • The Client: The last part you will want to review before submitting a proposal is the client. You don’t get much information from the project ad alone, but you can begin to understand how reputable they are. Suppose a client asks for significant work (say 10x articles at 800 words each), offers minimal pay, and doesn’t have any freelancer feedback. It’s probably not going to work out. 

When clients don’t put any effort into their project job descriptions, this can be a red flag for a dead-end project. Sending proposals on Upwork can cost anywhere between 2-6 Connects, which cost money – so don’t waste them. 

Instead, be smart about who you send proposals to because you are in charge of who you work with.

Now that we’ve addressed each part of the clients’ side of the project, it’s time to work on our proposal. 

Proposal Examples

The best way to write a project proposal is to look at some good and bad examples. Below are two examples of proposals for the project featured in the image above. 

  • Example One: Hey! I can help you out with your project. I have been freelancing for many years now and believe I can help you with your project. I can write all 5 blogs for your website; I charge £40 per article. Check out my portfolio. Thanks!

Example Two: Hey there! My name is Kyle, and I’ve been copywriting for over three years. Currently, I do a bit of everything in terms of writing; specifically, I excel at blog posts by capturing and executing tone. I’ve worked on several blog posts in the past as a ghostwriter, so I’m familiar with writing as someone else with a specific audience in mind. Regarding your project, I’d love to start some discussions about the kind of content you’re looking for and what I can bring as a copywriter. I usually charge £35 for a standard 800-word article; however, I’m sure we could come up with a bulk discount given the number of pieces needed. The bottom line –  my writing will keep your readers reading. If that’s what you’re after, drop me a message, and we can discuss some details. Kind regards, Kyle Clark.

While Example One isn’t necessarily bad, it’s not good either. When possible, you should always direct your proposal to a named individual. If the client hasn’t left a name or company, default to something like, “Hey there!” or “Good morning!”. 

You may notice that Example One states what I can do for the client without any actual evidence to prove I can do this.

Whereas Example Two demonstrates my abilities and how I’ve proven this in the past. If you can express confidence in your proposal, the client will notice this and be more likely to pick you for the project. 

Notice how the client never specified a word count for the work; this means you may not be able to quote an accurate figure for the client. Instead, consider mentioning the services you offer and the costs; this will highlight your skills and confidence in the matter if you’ve already considered pricing before writing the proposal.

Discussing Price 

Discussing your charges as a freelancer should not be an awkward conversation.

You are a professional who deserves fair payment for your work. Keep this in mind when reviewing independent contractor jobs that seem a bit low payment-wise. 

Also, remember that some clients will specify how much they’re looking to pay by the hour. Make sure this is reflective of what you expect to get paid as a freelancer. 

Ultimately, Upwork is a fantastic service that genuinely helps freelancers launch their careers. The key is to use your eyes, not rush the proposal, and make the client want you.

Follow these tips, and you’ll be landing your first client within days.

Kyle has over three years of freelance copywriting experience, specialising in ghostwriting articles and blog posts. From how-to guides to lifestyle writing, Kyle adapts his writing style and tone for the intended audience.


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