Feature: Upload cover letter as PDF (like resumes) and select when adding a job

[AkshayChikhalkar]

Summary

Allow uploading a cover letter as a PDF (similar to resume file attachments), and selecting an existing uploaded cover letter when creating/editing a job — instead of only authoring plain/rich text in a separate Profile tab.

Problem

• Cover letters today are text-only (title + content) on the Profile Cover Letters tab.
• Resumes already support uploading/attaching a PDF/DOCX file and assigning that resume on the job form.
• Users who already have a PDF cover letter must re-enter or recreate it as text, which is inconvenient and can lose formatting.

Proposed solution

Mirror the resume flow for cover letters:

1. Upload — On Profile, allow uploading a cover letter PDF (and optionally keep the existing text editor for AI-generated / typed letters).
2. Store — Attach a File (or equivalent) to CoverLetter, similar to Resume.FileId.
3. Select on job — In Add/Edit Job, keep (or improve) the Cover Letter dropdown so users can pick a previously uploaded cover letter, same pattern as Resume.
4. Download/view — From Profile (and optionally Job details), download or open the attached PDF.

Acceptance criteria

• User can upload a PDF cover letter from Profile
• Uploaded cover letters appear in the Profile documents list with download
• Add/Edit Job Cover Letter dropdown lists the user’s cover letters (uploaded and/or text)
• Selecting a cover letter on a job persists coverLetterId correctly
• Ownership checks apply (user can only use their own cover letters)
• Existing text-based cover letters continue to work

Out of scope (optional / follow-up)

• AI generation into PDF
• Multi-file versions per cover letter
• DOCX support (unless easy to reuse resume upload path)

Alternatives considered

• Keep text-only and ask users to paste PDF content — poor UX and loses layout.
• Store PDFs only as notes/attachments on the job — does not reuse across applications.

Related

• Resumes already support file upload via Resume.File / Profile upload flow
• Related history: Feature request - Resume/Cover letter in jobsync #11, Feature Request: Add Cover Letter and Comments/Notes textarea to the Add Job form #49 (cover letter on jobs / resume+CL tracking) — this request is specifically PDF upload parity with resumes