5 Lessons from 300+ Upwork Proposals
My theories for increasing the likelihood that your Upwork pitches will actually get a response.
Since my first Medium article about Upwork was a moderate success — I’ve made $0.41! And I’m STOKED! — I was inspired to try writing a follow-up.
The first piece was 5 Upwork Proposals that Landed New Contracts, and was basically just me plagiarizing myself because I’m slowly trying to come out of my shell as a writer. There’s a ton of advice about how to approach writing proposals, but I thought actually seeing real examples of successful pitch messages would be helpful.
Now, here’s some additional advice that includes no real examples whatsoever. These are some of the things I’ve figured out over time after sending hundreds of Upwork pitch messages.
Rule #1: Look for Recent Job Posts
This isn’t necessarily a deal breaker, but the longer it’s been since a job was originally posted, the more likely it is that the client is overwhelmed with proposals. If it’s a job with a reasonable budget (and especially if it’s SEO), there will be a fair amount of competition from other freelancers on the site.
One of my clients was still getting proposals after they’d already made a decision about who to hire, so if the job is more than a week old, there’s a good chance you’ll be pitching into a void.
It may be possible to get a response if you submit a proposal to a job that’s been up for a while and already has 10–20 proposals. But I’ve found that it’s a lot easier to get a reply when you’re one of the first people to respond to a new job post.
Rule #2: Don’t Copy and Paste
Nobody wants to read low-effort sales messages from random strangers. I’ve heard from a number of clients that they received a lot of proposals that were obviously a template or straight up copy-paste.
Clients like to get customized messages, so while it can be tempting to copy and paste proposals, the added efficiency you get from doing this basically just wastes connects. You may be getting a lot more proposals out if you don’t take the time to customize them, but clients can tell from a mile away that you didn’t bother to read their job post.
This is why you’ll see job descriptions that include some kind of keyword to use in your cover letter. The number of freelancers who don’t bother to read the job description is sufficiently high that clients have resorted to finding ways to filter out people who either lack attention to detail or simply didn’t bother to read the whole description.
If there’s a specific instruction in the job post, make sure you include it in your proposal. Employers use these to quickly weed people out. Specifically to weed out the freelancers who copy and paste proposals without
Rule #3: Don’t Get Discouraged
It’s best to have a thick skin and not put too much time or effort into crafting the perfect proposal, because there’s like a 90% chance the client won’t even reply to you. Or, perhaps it’ll be a scam. (Those do exist. Watch out.)
At some point, I remember reading a statistic from Upwork that it takes 5 pitches to get one response. That seems pretty low, to be honest. If you read the community forum, you’ll see comments from freelancers who have sent 30+ proposals and not gotten a response. Not even a rejection!
This is common, especially if you’re first starting out. It’s easier to get clients to notice and reply to your proposals once you have a bit of a work history and good reviews.
Everybody has to start somewhere, though, so even though it might seem impossible at first, you’ll eventually start building your Upwork reputation. It gets easier over time, I promise.
Rule #4: Include a Call to Action
The first step of any sales negotiation, or job interview, is to start a conversation. Your primary goal is to get the client to reply to your proposal, so it’s helpful to ask a question or request more information in order to get them to respond.
Often I’ll ask for a link to their website, since Upwork seems to discourage people from sharing URLs and other identifying information (probably to prevent people from bypassing the platform altogether — they want their 20% cut.) Giving the client a clear, direct request to reply to your proposal is helpful for starting a dialogue.
You’ll find that a lot of job posts lack the necessary detail to even put together an actual proposal. When the job description is vague, that’s a great opportunity to request additional detail.
Rule #5: Keep Your Pitch Messages Short
I have a tendency to write way more than is necessary. I’m convinced that grad school permanently destroyed my ability to write in bullet points. My preferred mode is the email version of a 20-page midterm paper.
Not only is it more efficient to craft short pitch messages, you’re more likely to get a response if you avoid writing a giant wall of text that no one will read.
I’ve tried both approaches — extremely long, detailed pitches and 1–2 sentence messages. Much to my surprise and disappointment, I almost never heard back when I spent time writing a mini-novel. But I did occasionally get hired after sending a two sentence message.
People are busy, and attention spans are dwindling. Be direct, succinct, and clearly communicate your value. You don’t need to share your entire life history with a prospect.
(I mean, you can. But that doesn’t mean that you should.)