Tip and Different Strategies for Writing Winning Proposals

Everyone says not to talk about themselves in the proposal. I more or less only talk about myself. My experience and expertise are what sets me apart from other writers in my niche, so unless I highlight that, there's no reason why a client should consider hiring me for 2-3x the rate everyone else proposes.

Eve Agreed. I talk about myself in the context of what I can/plan to do for them... but it seems a lot of people just send generic stuff about themselves, not acknowledging the job poster's own problem. If you're talking about you in the context of them, what more can anyone do to personalize? Sounds about right!

However—ten years ago or so, I read somewhere that a lot of "I/me" in written correspondence comes across as weak—so while talking about accomplishments or plans in a proposal, I tend to bullet-point things, chain together with commas, or phrase in terms of what the previous client got or what this client will get, so the actual word "I" isn't there as much. No proof it's done anything in terms of $$$, but it's become a habit and... I do think my writing's better because of it. More varied in sentence structure, at least! (For instance, this has been rephrased in at least 5 places so it wouldn't be so full of "I/me.")

Vladimir If repeating myself is okay, I've copied this from my answer on
https://freelancer.forum/public/d/71-what-to-keep-and-what-to-remove-from-a-proposal/2

Here's what I do:

1. First, I read their reviews. If anybody has mentioned the job-poster's name, I use it.

"Dear David,"

Bots, as far as I know, can't do this. And the object of the game is to demo quickly that you aren't a bot. Some folks say bots/AI are up to 90% of the sludge employers get right now.

2. Then I mention the extras they can't see unless they click. Is this the very best way to do this? I don't know, but I've only got 100 characters, or whatever the official limit is, and I'm trying to get that click.

"I hope I've answered all your questions below. Please see attached goodies for even more info!"

3. After that, I used to get right to personalizing, showing I've read what they're asking for: "Yes—I would love to work with you on the brand focus and identity for your rising home furnishings business." But now I save that for after the 100 characters, and instead jump to bragging up front:

"Recent projects: developed a name and logo for a legendary Silicon Valley venture capitalist forming his own firm; produced brand focus and naming/ tagline work for..." (etc.)

I've tested both—although Upwork click-through rates are dismal no matter what in the last two years, at least for me, bragging up front seems to work better.

4. Then the "Yes" part above, and specifics of how their particular project will go:

"For this project:
—Once we agree on the project parameters
—You XYZ...
—I'll ABC...
—Last 123..."

5. ... along with how many hours the project will take (so they are clear on the price from the start), a final thank you, signoff, and a P.S. (Long-form copywriting wisdom used to say that most people read the P.S. first... who knows if that's still true, but if it's a good P.S., it doesn't hurt!)

————

Having said all that: I am not a million-dollar Upworker. Just someone with many years of experience working for myself off-platform, and several years on the site, testing like heck to figure out what clients and the algorithm want from me. I've had many prospective clients write back to say "this is the best proposal I've ever gotten on Upwork," and to thank me for answering all their questions so we can get right to solving their problems. But that hasn't made me a million-dollar Upworker, or kept me from experiencing the horrible slide lots of other people have seen on the site. These days, I hover between frustrated and disgusted with the site and my ability to break through, most of the time.

So take what I say with a grain of salt, except this:

• Keep your own stats. Upwork's stats are opaque, misleading, and not as detailed as you can keep yourself.
• Test, test, test. If your own click-through rates, contact rates, or hire rates are better with X approach or Y approach, and you don't realize it, you may keep doing Z when you should be doing X or Y!

Eve Well in your case it was probably something like I am Eve and I have written more casino content than any other human on the planet.

When I give this advice it is because most people say things the client already knows:
Hello, my name is Mark F {shown on the profile} and I am a Top Rated freelancer on Upwork {well, duh} and I have been programming computers since Jesus got his wisdom teeth out. I am really interested in your job here because I like money a whole lot.

I suspect your proposals are not YOU-centric, they are why YOU will completely solve the clients problems.

Kelly_E

"Dear David,"
Some client's have told me that they hate this and when giving them reviews not to put the name in there. I only respond with a name on an invite if they gave it to me.

Bots, as far as I know, can't do this
I don't know a lot about AI or bots but I could definitely do this

Then I mention the extras they can't see unless they click. Is this the very best way to do this? I don't know, but I've only got 100 characters, or whatever the official limit is, and I'm trying to get that click.
I love this tactic...Hello Mr. Client I have all the answers you need and all you have to do is keep reading
I do the same thing but also state problems they are going to run into but make sure to take my time getting to it so they have to read through.

Mark Wow—I've never had anyone say they didn't like my having read enough about them to know their name.

I got this tip waaaay back when I was a baby Upworker from the onboarding (remember when UW was serious?)—they said proposals with a name did way better, so find it in reviews and use it.

(Do they do better? I dunno.)

Heck, if they gave enough away in the job listing, I'll even go to their website, do a little more research on what I'll say in the proposal and also find the likely job-poster's name/s, and then write "Dear David, Rick, and team" (the "and team" is in case David and Rick didn't really post, while the names let them know I did my homework).

This is also the advice people always give to regular, résumé-sending job hunters—do your homework and show it by referring to people by name.

...

I love that idea of stating problems they're going to run into! As the old copywriting advice goes, use any hook that works—but use a hook.

The only job of the first sentence is to get 'em to read the second sentence. The only job of the second sentence is to get 'em to read the third...

Mark Now I had to check, and I have written more than 1 million words in 2024. So my best guess would be that I'm up to somewhere between 8 and 10 million words lifetime now.

The main thing I talk about is that I've worked more than 10 years in this industry and that especially my in-house experience as a trainer for new employees is what enables me to explain how casinos operate in a way people understand. And since I mainly write reviews or guides, that comes in handy. Other than that I just tell them to have a look at my Upwork work history or Google me. Not sure if we're allowed to ask clients to Google us, but so far Upwork hasn't told me to not do it.

I've hired a lot of writers for my niche on Upwork, for various different projects I've worked on, so I've read proposals from hundreds of writers. And what 95% of them lack is any real experience and knowledge about the industry. Most just say "I've written hundreds of reviews of online casinos," and that doesn't mean anything to me. Just because you've written about something doesn't mean you know what you're talking about. So my main point in my proposals is that I actually know this stuff, better than most other writers on Upwork, so "me" is the selling point in my proposals.

In my niche, most clients hire new writers all the time, because they're not happy with the ones they've already got. They know the general quality is bad, and that most of tham have no idea what they're writing about. So that's where I stand out, and clients can see that when they look at my profile, since I have a lot of long lasting contracts.

I know this doesn't work for everyone, but I think that if you charge way more than most other freelancers in your niche, you need to expalin why that is. And from that a client will understand why you are the one that's best suited to solve all their problems.

Eve

Not sure if we're allowed to ask clients to Google us, but so far Upwork hasn't told me to not do it.

When relevant, I tell clients (and it's on my profile) about being named a Top Writer on Quora multiple times, and other external recognition, and they could easily check any of that out... so I assume unless you explicitly mention a method of contacting you, it's all just burnishing your reputation, which is allowed.

In my niche, most clients hire new writers all the time, because they're not happy with the ones they've already got.

Mine too. Honestly I avoid job listings that have a whiff of "this was already done and I didn't like it" these days. I find those clients have been SO burned by a bad Upworker, that it's hard to get them back to understanding I'm a long-time professional and expert at what I do. They've decided just to look for a slightly-less-bad-Upworker, and it's too much to get them on the bandwagon.

Of course, 9 times out of 10, the reason they're not happy with work that's been done is because they tried to get something for nothing, which is its own problem... sigh

Kelly_E Personally, when I hire on Upwork, I don't like it when freelancers mention my name. I'm not sure why, but it feels invasive somehow. I don't know them, they don't know me, and it just feels like they've been snooping. I also almost never even open proposals when I see them starting with "dear." Also too personal for me. This might just be a cultural thing though. In my proposals, I just say "Hi" and leave it at that.

Eve You have a great story to tell, most people do not, and even if they did, wouldn't know how to tell it.

Kelly_E A client that has had bad experiences with other freelancers before is basically my target client. They're the ones that will appreciate the work I do, and also understand why I charge more. Those and brand new Upwork clients. The worst ones for me are those that have been around for a couple of months or a year, and are still looking for a dirt cheap freelancer that can do excellent work.

Mark Yeah, I agree. A lot of freelancers do it, so I assume it does work. But it's just not for me.

I think one useful thing to know is that when a client opens a proposal, the answers to their questions are shown on top, so that's the real introduction. The cover letter seems more like a continuation.

My first sentence is usually something like
"Hi, thanks for reviewing my proposal. I have 10+ years experience working in the iGaming industry, both in-house and as a freelancer."
Maybe that comes across as psychotic, but I don't really care.

Looking at my stats, 2/3 of my proposals are viewed, and I'm not sure, but I think as an average for Upworkers that's not too bad.

And yes, I also turn down a lot of jobs. Two only this last week. I'm not interested in working with clients on boring projects or with clients that seem nightmareish. Steady long-term work with clients that treat me as freelancers should be treated are the only ones I'm interested in.

Eve "Dear" is out? Darn, that makes me feel old. I haven't written a real, snail-mail letter in forever, but of course I still remember that you would never start a real letter without it... and the whole point is trying to feel real...

Time to test "Hi David" vs "Dear David." After all, I just said test test test!

From the stats I keep (also mentioned above)—name gets more clickthroughs than no name. When I said above that I don't know if it does better, I meant quality—I don't know if the ones that don't click might have been the better jobs, etc. Like you! And I haven't had Mark's experience with anyone telling me directly that they disliked personalization—as I mentioned, people who do specifically talk about the proposal, always say really positive things.

This is such a lot of food for thought!

Hmm... having worked for myself for a long time before UW, and trying to wrangle something out of UW for years now as well.... Proposals are like dating—trying to find two working styles and personalities that mesh. So... if there are job-listers that wish I hadn't done that homework to find out more about them and save us both time... well, they probably aren't going to like the rest of the proposal, either—because if I can get us "matched" or unmatched before we've even spoken, that's what I'm trying to do!

Kelly_E I think it completely depends who your clients are. Most of my clients, and frankly most people in my industry, are in their 30s. And they're usually quite laid back and, maybe most importantly, European. We're not very formal. Even when I worked in-house, we never started emails and such with formal greetings and all of that. Usually, it was just "Hi Kelly," "Hello" or when extra lazy, just a smiley face. Haha!

So the important thing is probably that you communicate in a way that resonates with your clients. For me, that means being informal.

Kelly_E

"Dear David,"

I used to do that until I started hiring for a client and proposals sent to me started with "Dear David" which I found mildly irritating.

I also (funnily enough the same week) got told by a client that she thought that it's creepy and she actually asked Upwork to remove her name from reviews.

Ever since then I just start with "Hi".

Kelly_E

Wow—I've never had anyone say they didn't like my having read enough about them to know their name.

Would they tell you though? I've had a client tell me, talking about other freelancers. She said she felt it was creepy, and having been called by the previous person's name when I took over handling a client's freelancers wasn't great either.

Petra I used to do that until I started hiring for a client and proposals sent to me started with "Dear David" which I found mildly irritating.

Same. I've hired from the same account as several other people, and it's annoying to be greeted by another persons name. Almost feels like I have to start the conversation explaining who I am or apoligizing for not being that person.

Petra Well, as I said (someplace above), people might not tell me something negative or I might simply miss out on some very fine folks who didn't reach out at all—but all the things that have been mentioned about my proposals have been high praise... in fact, kinda higher praise than I expect, but I have been making proposals to clients for a very long time so maybe I really do write "the best" proposals that (some) people have seen (in my field) on UW?? I can't really fact-check that, haha...

But yeah, as also mentioned someplace above, it's advice written into Upwork's own onboarding & FAQs (unless they've updated it)—so between UW's recommending it and it seeming in my mind (and from occasional direct feedback) to be a good way to do things, I've just continued on with it.

It appears, from this very interesting discussion, that it's time to see what happens to my stats if I do the pre-click intro differently.

When I started out and realised (because I hired on UW) that the first line counts, my stubbornness got the better of me and I decided to start my cover letters with a "thank you for..." Because I was genuinely grateful, but also because I want clients to CLICK ON THE **** THING if they want to find out more. Probably not best practice, though.

For those who do consider it worth their time to read my cover letter in full, I sometimes add my time zone and business hours, especially when the client mentions response times and availability as a criterion.