Case study match

On Upwork a freelancer can attach past jobs, portfolio items and certificates to a proposal in its Profile highlights section, but Upwork notes that "this feature is not available to agencies". An agency's evidence has to live in the cover letter, which makes choosing the right example a large part of a good letter.

The match runs per job. Each case study, its title, project, challenge, solution and result, is turned into an embedding and refreshed when its text changes. When a letter is drafted, the job post is embedded too and every case study is scored by its similarity to it, plus 0.02 for each job skill the case study names, counted up to three so that meaning leads and tag lists do not. Pinned case studies are always offered first; the remaining places go to the best matches, five in all. The writer may cite at most two, and only where one genuinely fits.

If the match cannot run, the writer falls back to the profile's first eight case studies in the order the agency set, which is why order still matters and the editor marks where that line falls.

Each draft stores which case studies it was offered and why, so a reviewer sees the choice next to the cover letter. What is not yet measured is reply rate per case study: which examples earn replies when cited, compared with the same examples offered and left out.

How Upsight uses it. The knowledge profile editor shows each case study with pin and order controls, and a preview shows which case studies a given job would be offered before any letter is written; the same preview is available through Upsight's MCP server.