These 5 Upwork Proposals Landed New Contracts: How I Get Clients

Jess Rohloff
Oct 26, 2020 · 10 min read

Wondering how to get clients to respond to your Upwork pitches? I don’t have the answer. But here are five proposals that generated new business.

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Photo by Clem Onojeghuo on Unsplash

Some writers who give advice to new and aspiring freelancers caution you to avoid Upwork at all costs. They’ll say things like:

“It’s trash.”

“It’s a race to the bottom.”

These writers aren’t entirely wrong. There are a lot of things I actively hate about Upwork, for sure. But I’m also of the opinion that the site can be worthwhile. I’ve found some absolute gems on that site.

But it requires a lot of patience to sort through the crap, and you’ll send many proposals into the void only to be met with silence (or, if you’re “lucky” straight up rejection).

While digging through the archives of my submitted proposals, I realized that over the years I’ve sent almost 300 proposals. My lifetime billings report shows a grand total of 8 clients totaling $6,180.00 in payouts.

Minus the 20% cut Upwork takes, that’s $4,944.00 in profit.

So, on average, I’ve made $618 per client.

Landing 8 clients out of 275+ pitches is arguably not a great batting average. But honestly I don’t care. It’s par for the course. (Shall I mix my sports metaphors further? Something about touchdowns or a Hail Mary, perhaps? Moving on…)

Upwork may not be the ideal way to grow a serious freelance business, I would argue that it isn’t the 9th Circle of Freelancer Hell that some people make it out to be.

My opinion is that Upwork is a lot like Craigslist. Treasure can be found if you’re patient enough to sift through the scams, spam, and offensively low-budget posts. It’s honestly one of the best ways find companies looking to outsource specific projects (vs. hire an employee) that I’m aware of at the moment.

This is helpful if you haven’t built an inbound marketing system yet. Or if you’re just starting out and don’t have a substantial professional network. Referrals only come from people who know you. Upwork can be a great way to build your reputation and gain some confidence that yes, you really can do this. People will pay you for [insert work].

(You totally can do this, by the way. I promise.)

So even though Upwork is super shitty in some ways, I do have to admit that I’m grateful it exists, because it’s helped me land some truly fantastic clients.

I dug through my proposal archives on Upwork to share some actual pitch emails that successfully landed a client. Hopefully this information will be useful as you’re trying to figure out how to get started.

Pitch #1: 2000 Word Article Needed on Downstream Oil Refineries in Alaska

This one was intriguing, because it was about a technical subject I randomly happened to know a few things about. Also, it paid like $450, which felt like a ton of money at the time.

In fact, for some reason in my memory the budget felt like it was in the four figures, so I am surprised and amused to see that it definitely was not.

That said, I landed the client, and ended up writing for Alaska Business Monthly Magazine for 6–7 months. So I did end up making several thousand dollars from this client. Most of that was outside of Upwork.

The job post was “seeking [a] talented writer to research/write article about how downturn in oil and gas industry is affecting downstream refinery jobs…” and so on, in a similarly exciting manner.

I’m a nerd and genuinely get excited writing about the most boring shit imaginable. So this was right up my alley!

Here’s my response:

Greetings! My name is Jessica Rohloff, and I’m a freelance writer with experience in the Oil and Gas industry. I used to work for HexArmor, a safety glove manufacturer in Grand Rapids, Michigan, and much of my job as a senior copywriter and marketing strategist involved researching and writing about the oil industry.

This sounds like an interesting project, and I’d love to help out! I’m good at research, so I may be able to find some additional data to support the article in addition to the resources you provide.

Thanks for your consideration!


Are you familiar with meeting short deadlines? Please include three published writing samples. Article must be researched and turned in by May 20th, 2017.
Yes, I’ve turned around writing projects in less than a weekend, so I’m very familiar with tight deadlines. I’ve attached two writing samples, and a third one can be found here: [url redacted]. This article was ghostwritten (by me) for a client. I have other writing samples if you’d like to see them.

Do you have any questions about the job description?
The deadline is May 20th: what does the final product look like, exactly? Are you expecting it to be formatted in a certain way? Does it need to include supporting graphics like charts or graphs? Where will the article be published? Is it meant for the web (i.e. a blog post), a trade magazine, or some other outlet?

What past project or job have you had that is most like this one and why?The above-mentioned job at HexArmor is definitely the most like this one. I wrote a white paper on hand safety (see attached), which I think is similar to this project.

Why do you think you are a good fit for this particular project?
I’m great at research (both primary and secondary sources, primary usually meaning interviews with people involved in the subject matter), and I can turn things around quickly. I have some familiarity with oil and gas, and think I’d be a great fit for this writing project.

This message led to a phone call with the Managing Editor of the magazine. She’d apparently hired someone else on Upwork who completely dropped the ball and left her in a pinch. (This is a common occurrence, and I’ve stepped in to pick up a previous freelancer’s slack or fill in when they straight up ghosted and left the client in a position to blow deadlines and start to panic.)

I ended up getting a totally different assignment than the one described on Upwork. My first article for Alaska Business was about search and rescue operations, which I knew absolutely nothing about.

You can read the final result here: Saved by Alaskans (PDF link).

Pitch #2: SEO Help — Getting links on individual teacher sites

This client was looking for “help in getting specific text like ‘Math Worksheets’ to our site on individual teacher sites or schools to link to us.”

Aaaand… That’s it.

Literally a one-sentence job post.

But it led to one of my best-paying clients on Upwork to date.

Something that works for me with SEO-related projects is to provide some value up front if at all possible. It’s harder if you don’t know the name of the company or have a URL to work with, but in this case I was able to run some Ahrefs reports based on the keyword mentioned.

Hi there! My name is Jess. I’m a freelance writer, marketing strategist, and aspiring SEO expert. (I say “aspiring” because SEO is such a complex topic, true experts in the field are *rare.* In my opinion, anyway. :)

I’d love to help with your backlink strategy! However, I would caution against over-optimizing the anchor text in your backlinks. This blog post explains why: (If you don’t have time to read the whole thing, I’ve attached a screenshot of the relevant section.)

I ran a quick report on’s backlink profile, and as you can see, you’ve already got a bunch of sites linking to you that mention your target words in the anchor text.

Can you give me a bit more information regarding what you’re trying to achieve with this project? I’m sure I can help you get backlinks… But I’m guessing there’s more to it than what you mentioned in your Upwork post.

Let me know if you’d like to chat!


This was an awesome client to work for. It’s the only time I’ve ever worked exclusively through Upwork and email with someone – every other client relationship began with at least one phone call. But Russ was never interested in hopping on the phone.

Unlike most of my other clients, this one was an experienced Upwork user. I’ve had a lot of clients who were trying Upwork for the first time, and they weren’t super comfortable with it. This guy was, and he was a pleasure to work with.

Pitch #3. Content Writer with SEO Background Needed for Multiple Clients

This client was looking for “a content specialist that can help manage all content needs for my various clients. I have 3 sites in the following niches: automotive, car warranties, taxes.”

It went on to say that “sample tasks may include” writing 2,000 word articles with a focus on a specific topic and keyword, perform keyword research, etc.

Here’s my proposal:

Hi there! I’m interested in the SEO content specialist position you posted. I’m particularly excited about developing content ideas based on target keywords.

Do you have any experience in SEO?
Yes indeed! Many years ago, for no particular reason, I decided to take over the first ten Google search results for my name. (Successfully, I might add.)

The results from that project led to an opportunity to help work on a huge SEO effort for United Airlines. (My mentor and his team had achieved #1 placement for UA for the words ‘airline’ and ‘airlines.’ I got to learn how that was done and also help UA maintain their position. Until budget cuts ended the project, but still. Super cool!)

I’m primarily versed in on-page SEO strategies. It doesn’t sound like you’re looking for someone to conduct a link building and guest blogging campaign, but if so, well…I can learn!

How many hours a week of availability do you have?
My availability is pretty open at the moment. I can be available anywhere between 10–30 hours per week. Or more, if needed.

The response I got from this client was super encouraging. Still makes me happy three years later.

Here’s his response:

Hey Jessica,
I’m pretty impressed with your proposal.

Your rate’s a bit higher than what I was looking for as I was scouring VAs in the Philippines for this role.

But you’ve peaked my interest.

Do you have any samples of your work that I can review?

So I sent a bunch of links to things I’d written in previous day jobs (including the Alaska Business Monthly article linked above). None of them were relevant to the niches listed in the job post, so I just sent a selection that showed my various writing styles and output.

The client ended up hiring me, and we worked together for a few months. It was my first (no, second) international client.

He was based in Vietnam, a 12 hour time difference, but we both kept odd hours so our meetings would take place at 1am/1pm — taking turns being the one up and working past midnight.

So in this case the time difference, well, didn’t make a difference.

I took this job for approximately 1/4 of my target hourly rate, and the client paid me approximately 4x what he’d been planning to pay a VA in the Philippines. It worked out for both of us, though.

The contract ended when one of his clients ran out of money. It was a fun project (despite horribly boring work — I was writing about taxes) because the client was awesome. I’d totally work with him again.

Pitch #4. Need help creating Customer Experience Management articles

You’re probably getting bored with the backstory.

Am I starting to sound like those recipe websites that make you read the author’s entire life story before just giving you the damn recipe?

Here’s my pitch:

Hi there! My name is Jess Rohloff, I’m a freelance writer and marketing strategist, with strong opinions about the topic you need someone to write about. I firmly believe that every interaction a customer has with your business either improves or deteriorates your company’s reputation. Basically, every interaction should be considered “marketing.”

I’m interested in this topic, and would love to know more about the position. Would it be possible to set up a time to chat, either over the phone or via Upwork? I’d love to know more about you, your company, and what you’re trying to achieve with your content strategy.

Thanks so much!


Got hired, loved the client, finished the project and everyone was happy.

He then ended up getting a new job at another company, and hired me outside of Upwork to continue to write content.

Pitch #5. Need help with a few blog posts

This job post was exceedingly vague. The entire thing was one sentence. “The first project will be a blog piece on a real estate concept we’re looking to demystify for the industry.”

So, my proposal email was equally succinct. No attachments, no industry experience data, just this:

Hi there! My name is Jess, I’m a freelance writer and marketing strategist, and I’d love to know more about this project.

Please let me know if you’d like to see writing samples, or if you have any other questions for me.

Thanks so much!


There was very little back and forth with this client. I think that my Upwork profile did a lot of the talking for me with this one.

We had one short (and if I’m being honest, fairly awkward and unnecessary) phone call. Which I think was mainly so the client could prove to himself that I was a real person? It was unclear.

In any event, I did some writing, and got paid.

The end.

Conclusion: Did Any of this Help?

Yes, my conclusion is a question. Were these examples helpful for you?

In a future post, I’ll share a list of the things I’ve learned about sending successful Upwork proposals. Timing, CTA (call-to-action), avoiding cookie-cutter proposals. Things like that.

For now, I just wanted to share some verbatim examples so others could see what’s worked for me in the past.

Thanks for reading, and thanks to the Gregory D. Welch for writing “Why Your First Focus Should be Finishing What You Write.” That was the kick in the ass I needed today to get this thing done and published.

Hooray! First Medium article = complete. Finally.

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