I’m a freelancer who’s made more than $500,000 on Upwork. Here are 3 proposals that won me gigs online.

Morgan Overholt

When I first joined Upwork as a freelance graphic designer in 2017, I knew learning how to send an effective proposal to win well-paying jobs would be critical to my success on the platform.

Over the past four years, I’ve earned more than $500,000 on Upwork alone, applied for 819 jobs, and won 223 with a 27% average hire rate. 

27% may seem low, but according to Upwork, I’m in the top one percentile compared to my peers. 

And it’s improving every day — my hire rate is 50% in 2021.

I have a couple words of advice:

It takes time to win quality work on freelance marketplaces

It took me two weeks of persistence before landing my first $10 contract in 2017. 

The reputation I’ve built on Upwork over the years allows me to earn the trust of prospective clients. Persistence is key.

I focus on long-term, ongoing contracts as often as I can

This helps me reduce the number of proposals I have to send. I’ve earned more than $147,000 on my largest long-term contract to date over the course of three years.

Creating a winning proposal template like mine was an iterative process. I spent years trying out different strategies and tweaking the formula until I came up with something that worked.

Over time, I’ve been able to home in on the specific elements that make my proposals so effective. Those include:

  1. The client’s name or a casual greeting
  2. A portrayal of confidence in my ability to do the job
  3. Details about my level of expertise and experience
  4. An indication that I read the job description
  5. Multiple portfolio options
  6. A bit of humor (when applicable)
  7. A genuine compliment (when applicable)
  8. A call-to-action

Here are three real-life examples of proposals that have landed me jobs: 

I made $6,900 from a cat-litter company looking for a ‘Digital marketer with graphic design skills’

screenshot of an Upwork job posting

I treat my proposal template like a sandwich — I keep the intro paragraph and call-to-action mostly the same every time but swap out the "meat" in the middle.

While I normally like to keep my core proposals brief (around 150 words), I do go into greater detail when a client opts to add one (or many) of Upwork’s prefab detailed questions to their job post.

Also, I’m never afraid to inject a little humor into my proposals when appropriate. I could tell by the client’s provided packaging samples that they had a great sense of humor — their brand was clever and full of puns. 

Finally, always include a client’s name when possible. While it’s not always easy to ascertain on Upwork, if you do a little digging you might be able to find it. The best place to look is in their reviews section located under the job post.

Here’s what I wrote to this company:

Hi [client’s name],

As you may have already read on my profile — I am a graphic design guru with 15 years of professional experience. I work with nationally recognized clientele on a daily basis, including the Centers for Disease Control (CDC), QuickBooks Intuit, and Kimberly-Clark (Kleenex). 

I have a hybrid background in graphic design and sales and am able to work with a variety of mediums, including digital and print – and of course banner ads, email ads, and even packaging.

I love your branding by the way! Very cute! The tagline made me smile. 

I am also fast and pride myself on my ability to offer quick turnarounds. I will attach a few design examples to this proposal. You can view additional work samples on either my Upwork portfolio or on my website: www.morganoverholt.com. 

Reach out to me here on Upwork and we can talk details! I am looking forward to speaking with you soon!

I made $37,800 from this posting asking for ‘Graphic design for books (and more?)’

screenshot of an Upwork job posting

I’ve made a habit of portraying confidence and writing in a matter-of-fact manner when sending proposals. I shy away from phrases such as "I think" and "I feel" and opt for phrases such as "I am" and "I will" instead.

While pre-contract, off-site communication was recently banned on the Upwork platform, links to portfolio websites can be shared privately. 

And if a client indicates a facet of the job is important to them, I pay attention to it. For instance, I could see that this particular client wanted someone fast and efficient. He asked for a designer that could complete the first assignment in under a week. 

I promised a one- to three-day turnaround in my proposal, and to make a great first impression after winning the job, I completed the initial task in less than 24 hours. Under-promising and over-delivering is always a highly effective strategy.

Here’s what I wrote in my initial outreach:

Hi there! 

I am a graphic design guru with 15 years of professional experience. I work with nationally recognized clientele on a daily basis, including the Centers for Disease Control (CDC), QuickBooks Intuit, and Kimberly-Clark (Kleenex).

I have a hybrid background in graphic design and sales and am able to work with a variety of mediums including digital, print — and of course print work and booklets!

I am also fast and pride myself on my ability to offer quick turnarounds — with most projects being completed within 1-3 business days.

I will attach a few design examples to this proposal. You can view additional work samples on either my Upwork portfolio or on my website: www.morganoverholt.com. If you have any questions at all — feel free to reach out! Looking forward to hearing from you soon!

I made $147,000 from this posting looking for a ‘Graphic designer needed for long-term project’

screenshot of an Upwork job posting
While a brief job description might be a red flag to some freelancers, I don’t allow a lack of details to get in the way when I apply. I find these jobs to be less competitive than others. 

It’s also proof that reusing and recycling a pre-packaged proposal template can be just as effective as writing something custom each time.

I knew this contract was a potential winner from the subject line. After completing the first assignment, the job grew to a multiyear contract.

Here’s what I sent:

Hi [client name]!

I am a graphic design guru with 15 years of professional experience. I work with nationally recognized clientele on a daily basis, including the Centers for Disease Control (CDC), QuickBooks Intuit, and Kimberly-Clark (Kleenex).

I have a hybrid background in graphic design and sales and am able to work with a variety of mediums including digital, print — and of course graphics, banners, and packaging.

I am also fast and pride myself on my ability to offer quick turnarounds.

I will attach a few design examples to this proposal. You can view additional work samples on either my Upwork portfolio or on my website: www.morganoverholt.com. If you have any questions at all – feel free to reach out! Looking forward to hearing from you soon!

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Morgan Overholt June 23, 2021 at 08:12PM

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