Your first AI proposal: 30-second walkthrough
A step-by-step walkthrough of sending your first AI-powered proposal from Upwork.
You’ve created an account, installed the extension and synced your profile. Now let’s send your very first AI-generated proposal. End-to-end it takes under 30 seconds.
Step 1 – Find a job
- Open Upwork’s job search:
upwork.com/nx/search/jobs. - Filter by your category and skills.
- Click on any job listing to open the details page.
Step 2 – Check Fit (optional but smart)
On the job details page the floating Upwex AI widget shows two action cards:
- Check Fit – runs an AI analysis of the job and prints Match Score, Red Flags, Client Info and tips. The button changes to View Results if you’ve already analyzed this job.
- Quick Apply (Pro and Max plans) – the one-click shortcut: Upwex generates the cover letter, answers screening questions and submits the proposal for you. If your plan allows it, you can skip Steps 3–5 entirely.
If the Match Score is low or there are serious red flags, consider skipping the job and saving connects.
Step 3 – Open the proposal form
Click Upwork’s Apply Now button on the job page. You’ll land on Upwork’s proposal form, where the Upwex Cover Letter widget appears.
Step 4 – Generate the cover letter
The Cover Letter widget opens with three action cards:
- Cover Letter – opens the prompt editor so you can pick a template and generate.
- Autocomplete – fills every field (cover letter + screening answers) without submitting.
- Auto Bid – fills every field and submits the proposal in one click.
For your first proposal, click Cover Letter → tweak the prompt if needed → click Generate. Within a few seconds Upwex inserts the generated text directly into Upwork’s cover letter field.
Step 5 – Review and submit
The widget switches to a success card. From here you can:
- Read the inserted text inside the Upwork textarea and freely edit it before submitting
- Click Regenerate in the widget to replace it with an alternative version
- For each screening question, click ▶ to generate an answer or ↻ to regenerate it
- Click Upwork’s Submit Proposal button to send
That’s it!
Each cover letter generation costs 1 AI Credit; each screening answer costs another credit. Your monthly allowance depends on your plan – see Understanding AI Credits for the full breakdown.