n8n Upwork Proposal Automation: Gemini + Slack + Gmail + Drive + ClickUp

Automate Upwork proposal generation every 2 minutes—Slack → Gemini → Gmail → Slack → ClickUp

This n8n workflow watches for new Upwork job posts in Slack, matches them with candidate resumes and a company deck from Google Drive, generates tailored proposals using the Google Gemini API, then sends proposal emails via Gmail, posts results back to Slack, and creates ClickUp tasks for tracking.

What this workflow does

• Runs on a 2-minute schedule and checks a specified Slack channel where Upwork jobs are forwarded.
• Deduplicates incoming Slack messages using n8n static workflow data, so the workflow only processes new, job-like posts.
• Loads candidate resumes from Google Drive: lists PDF resumes in a configured folder, downloads each file, and extracts text to build structured candidate profiles (with Drive links).
• Finds the right company deck in Google Drive and selects its share link to include as proposal context.
• Generates proposals with Google Gemini by sending a structured prompt containing the new job post(s), candidate profiles, and deck link.
• Parses and validates the Gemini response (JSON array of proposals or skipped jobs).
• Outputs results automatically: if proposals exist, emails the proposal package via Gmail, posts a summary to Slack, and creates one ClickUp task per proposal. If none are produced, it flags the batch for manual review in Slack.

Use cases

• Agency or SaaS teams that want faster Upwork outreach without manually rewriting every proposal.
• Automation engineers building a proposal automation workflow combining Slack intake, Drive assets, and Gemini generation.
• Operators who need proposal tracking via ClickUp tasks and clear Slack alerts.

Technical details

• Integrations: Slack, Google Drive, Gmail, ClickUp (task creation) and Google Gemini API.
• Workflow nodes used: if, code, gmail, merge, slack, split out.
• Setup: add Slack OAuth2 credentials and set channel IDs; add Google Drive OAuth2 credentials and update the resume folder ID.