It's been years since I was on Upwork (started w/ Elance) and I felt similar frustrations. Then I signed up as a buyer, posted a job similar to the ones I was s

It's been years since I was on Upwork (started w/ Elance) and I felt similar frustrations. Then I signed up as a buyer, posted a job similar to the ones I was seeking, and analyzed the patterns of freelancer pitches and how the system was structured. I started noticing missed opportunities. As a buyer, you only see the first few sentences of a proposal unless you hit the See More option. Most freelancers weren't maximizing this space. NOBODY used video. There was minimal personalization. And so on. So I would make a personalized video for every pitch and reference it in the first sentence. Short, nothing with production or anything like that. Mostly I wanted the buyers to get a vibe for me. I'd do light research on the buyer and look at his/her feedback and reviews for other freelancers they've worked with, then I used that language to demonstrate that I had the same characteristics and skills they value the most. This all increased my interest and close rate tremendously. I also learned which gigs to never bid on, which is a little art and a little science. You can tell by how the project descriptions are written which ones to avoid.