If You Want To Win Upwork Jobs DON'T DO THIS

In this video Michael Elliott, a top‑rated Upwork freelancer who has earned over $500,000 and sent 5,000 proposals, dissects 43 proposals he received for a B2B SaaS PPC/Google Ads job. He shows that roughly 40 of them are AI‑generated, generic copy‑paste cover letters that ignore the client’s specific brief (stable MQL volume with dropping SQL conversions, need for offline conversion tracking, HubSpot/Salesforce attribution, and a performance‑max dilemma). He highlights common failures: lack of competitor research, no Loom audit, missing key requirements, and overly verbose introductions. Elliott then outlines a concise, high‑impact proposal framework: repeat the client’s problem, cite relevant competitor audits, attach a brief, state a one‑sentence opinion on Performance Max, list the three must‑haves (offline conversion imports, HubSpot/Salesforce attribution, 5+ years Google Ads experience), and end with a clear call‑to‑action. He advises using AI to generate research and polish the document, but not to replace personalization. The video concludes that the market is flooded with low‑effort proposals, and freelancers who adopt this minimalist, data‑driven approach can dramatically improve open and conversion rates.
Chapters
I just posted a job on Upwork for a PPC manager. I got 43 proposals in less than 18 hours, 40 of them written by AI, and I'm about to show you why this is the best news of your life. Because if you've been sending proposals on this platform and getting nothing back, it's because your approach looks like this. This is what you're competing with. I've earned over half a million dollars on Upwork, top 1% expert vetted, 5,000 proposals sent. I've never seen the bar this low. Not in 5 years, not ever. So we're going to do something. I'm going to share my screen and we're going to read these proposals together, and by the end of this video you're going to know exactly why your competition is in the most part garbage and exactly how to beat them. Let's go. Firstly, this is the job post that I put up: B2B SaaS intranet employee experience, similar competitors. I did that intentionally to see if anybody went deep on what any of them— it was relatively brief by design and it had a reasonable fixed price so that I knew that I would get applicants from it. When it comes down to the actual listings, let me just say something. I'm not here to slate any of these freelancers. They will be blurred out. This is not me attacking them, but you're— my audience are actively applying for projects, and you need to understand that AI is killing the heartfelt applications because AI is just swamping individual users. And as they're scanning, you're going to see exactly why you can make it stand out. So this was the job post for 43 proposals. Let's hit view. Now I'm not going to get a shortlist from UMA, but I'm just going to roll through these. My job brief mentioned stable MQLs, but SQL conversions dropped and nobody, nobody internally has a clean idea why. In here, every single one of these starts as an AI process. Stable MQL volume with dropping SQL conversion is a specific diagnostic. AI gone. Hi Michael, this is exactly the type of B2B SaaS problem I specialize in. MQM volume looks fine, but SQL conversion and pipeline quality have dropped. Usually because the account has been optimized toward. Let's have a look at this one. Copy and paste template. This is copy and paste. That's all copy and paste. So effectively that's dead in the water. When you scroll through these, cover the SQL drop with stable MQL, volume almost always points to the same thing. Attribution drift or audience bleed. AI, straight away, guaranteed, factually, AI. Bleed. Like nobody literally types this in. You can see, look, at $25K with 60 to 120-day sales cycles. Now listen guys, I tell you all the time to repeat the job post back to— the individual. You have to do that in order for you to capture attention. But just place yourself in the client's shoes as we go through this, because some of these have earned $200,000, $300,000 on the platform, and they're sending this quality of proposal. It's mental. Hello Michael. So they got my name. I can see that you need a Google Ads specialist, B2B experience. Doesn't stand out. Hi team, let me know if you want to discuss. I have about 10 years experience at the highest level. Bland, generic. Hey Michael, comes down to one of three things. Better, probably. Offline conversion tracking is exactly what I do. I've managed $10 million for a German edtech platform. So this is a relatively decent inquiry. This puts us in a position where he's actually given his experience, and from a B2B point of view. So give him like a 6, 7 out of 10. This is generic again. We'll go into the actual proposal, look at what they've done. PPC portfolio— where are the looms? Where are the people actively giving me information about my project? Where is the person that wrote back my competitors to me? Where is the person that attached— that says that they attached a competitor review? Where are they all? They're not here. New to But over 10 years experience, no reviews here, but plenty publicly available. Like this, let's have a look at this. He doesn't— they don't even say anything. Happy to audit the account before we speak. No pitch. Like nothing, absolutely nothing here is back to me. Now this one here was interesting, led with the Loom. Check my recent work Loom. But when I watched the Loom, the Loom isn't based around like my brief. The, the Loom is of his profile, effectively automated and AI-generated. Like there's no effort that goes into these proposals. Everybody says that They're gonna audit my project, they're gonna look through this. Nobody says to me, I've just reviewed X, I've attached the research documentation, 14 years fixing this exact problem, doing Y, and go straight at the jugular of the loom like I've shown you, like I've literally created videos about previously. Every single job post that we've clicked on and that we've looked through is like War and Peace. I've got 43 proposals to look through. I'm not reading this. Like, this is just— I'm gone as a business owner. I am out of there. None of this makes any sense. I've read through the role and this looks very aligned with the type of B2B SaaS Google Ads I've worked with and handled recently. Let's go into it. It'll be exactly the same thing. Here we go. Screenshots. They are dated, which is good, but like they mentioned the review. None of these open doors like Cheers MK. His name's Prem J. I'm going to have redacted that name that I just said there. It says Cheers MK and that's not his name. So you can see here straight away how you're not in a position to win any of these projects. There's not one here that I would look at. I'm literally scrolling through them and not one of these is straight to the point. None of them do it. There's no audit inside of here, guys. Honestly, I'm telling you, there's 43 applications. Weezy— I don't want to work with an agency. Zero completed jobs, but some of these have got $200K earnings. You can see it. And good success scores. Other proposals not relevant to your job or maybe one of your job qualifications. Applications. This cover letter has got to be the worst cover letter that I've ever seen. Hello, let's 10x your ROI as a Google Ads specialist with 5-star client rating and Upwork top rated for managing PPC lead generation campaigns for premium brands and services. Copy and paste, guys. Every single one of these documents, like, that they've put together— sorry, not one out of the whole 43 addresses and uses the key information that's inside of my job brief. So look at this: Happio, Staffbase, Competitor: ACVs, 18 to 90K sales cycle, targeted internal comms, HR, IT leaders. I would start this, and I'm just going to freestyle it. I would do a Loom covering this, and then my first line would be, I've reviewed Simpler and Happio's and Staffbase, whatever, trying to not take up real estate, but pick the competitors' PPC strategies and attached a brief. Literally, light bulb moment for the business owner. We've just scrolled through a bunch of things that say exactly the same thing. I would write that as the leading driver. They've given me their competitors. Use it. Use their competitors as part of the process. Sales cycle 60 to 90 days. Internal comms. Some people touched on this and trying to target the higher spenders, but I didn't see anything about targeting employee and companies like that have 500 to 10,000. Anything specific there? Then when it comes down to the, the HubSpot conversion tracking, strong opinion on Performance Max. Keep, kill, or restructure. I saw nothing about Performance Max. So my second line would be my opinion on Performance Max and that it can hemorrhage budget for businesses like you if not watched properly— things like brand exclusions, etc.— when it comes down to the monthly call issues. So let's just roll it back. First, I would use AI to generate a deep research analysis report and then put it into something pretty that just looks like there's effort there, that's factual. You don't have to write it manually. You can use AI with your applications. You just use it to help you deliver the best quality applications that you possibly can. You Then lead with their competitors. And if you've helped a competitor, even better. Like, if you've worked on something, you can lead in that. You change the verbiage, but the point still stands. Lead with that. Go back to them with their competitors. I've reviewed Simpler and Happier. They have very strong PPC strategies. Fear lit straight away. Then what other questions do they mention? They've got issues with the MQL and SQL, but everybody went really technical from AI saying how they would fix it. Just say that you're fully— like, I'm fully competent with I can build HubSpot and offline conversion tracking, no problem. Do it every day. When it comes down to Performance Max, generally speaking, in a SaaS industry like yours, I would kill it. Performance often over attributes, whatever you want to say that your opinion is in one sentence. And then about the monthly call, I'd probably say communication is king. Like it's something that majority— like the biggest compliment I get is my communication. Let's hop on a call and find out what your actual problem is, because until we speak, I can't See it, the must-haves: fluent in offline conversion imports, HubSpot or Salesforce attribution, and 5+ years Google Ads experience have to go into here. So as those 3 sentences are written out, because that's what you get, you get the timeline in terms of what you see by looking at the individual cover letter here. You can tell like you get about 3 sentences, so you have to fit all this in, but they're just quick ticks. You don't have to go into like crazy detail about the individual job. You literally just say, I've got 40— like me, I've got 14 years in the Google Ads space, mainly focused on B2B SaaS. That's half of a sentence. You finish the other half of your opinion on Performance Max, then you use their individual information back to them. I had 43 proposals for this project and not one of them did what they should. Why have I done this video? To give you the utmost confidence in your proposals. The— what you are competing against is absolutely diabolical. Lazy moves, generic openers, self-introduction before they've mentioned my problem. None of them mentioned anything that they'd actually produce for me. No value-add. Client name mentioning the businesses back to me. Nobody did that. Then you had people bidding $100 when I had that, lying about their credentials. As I've scrolled through, I've seen people say that they've got X amount of, of stuff on their profile and they didn't. I didn't open that one intentionally because I didn't want to like laser them out. The point I'm making, guys, though, if you do not take confidence from this, then you're in a position you'll never win an Upwork project again. So here's what you take away from it: you're not bad at proposals. You are if you're doing what they're doing. You're competing in a contest where 90% of the entries they're not even written by people, and clients can tell. They're just as fed up with it as you are. 3, 4 lines, real observation about their problem, a number that maps to their industry, want a question like today or tomorrow, when that— whether the call's due. That is the whole game in 2026, whether you're sending your first proposal or your 2,000th proposal. The freelancers winning on this platform right now are doing less than ever. They're just doing it deliberately. If you enjoyed this video, go and check this video out here. You will love it. Like, subscribe. But I had to do this. I had to see what I'm competing against them. If a client doesn't pick me after seeing my proposals— this is why my open rate is so high, this is why I get so many conversations and audits out of Upwork— because if that's what I'm competing against, I'm laughing all the way to the bank, and so are you.










