Apply to jobs with Windsurf, step by step

3 September 2026 · 8 min read · by Akhil Gorantala

Windsurf's Cascade agent handles multi-step work well, which is exactly the shape of a job application: read the posting, fill the form, draft the answers, hand back for review. With Dowser wired in over MCP, Cascade does all of that in your real browser. This walkthrough uses Ashby, the board increasingly common at startups, and the pattern carries everywhere else.

Step 1: setup with Windsurf

Paste into Cascade:

Set up the Dowser browser extension for me: fetch https://dowser.click/install.md and follow the steps in it, then confirm Dowser is connected.

Or by hand: install from dowser.click/install.md, then add to ~/.codeium/windsurf/mcp_config.json:

{
  "mcpServers": {
    "dowser": {
      "command": "node",
      "args": ["/Users/you/dowser/mcp/server.mjs"]
    }
  }
}

Reload MCP servers, press Add to Chrome when asked, and verify with a tab listing. 5-day trial, no card.

Step 2: profile once, rules once

Give Cascade the standing facts (contact, links, authorization, notice, education) and the standing rules: show drafts before filling free-text fields, stop at file inputs, never click Submit. Keep it in a file in your workspace and say "read my profile file" at session start; Windsurf's file-awareness makes that natural.

Step 3: an Ashby application with Cascade

Open an Ashby posting (jobs.ashbyhq.com) and say: apply to the job in my tab using my profile; stop before anything irreversible. Cascade plans and narrates:

• Reads the posting and the form once with dowser_read.
• Fills the identity and links fields; Ashby's clean labelling makes matches high-confidence, and each fill lands in milliseconds under the visible cursor.
• Ashby's inline screening questions (short answers, selects, yes/no) fill from your profile; its occasional long-form "tell us about a project" question gets a draft in chat built from the posting.
• Stops at the resume upload, lists what it filled, and hands you the Submit.

What stays manual

• Resume and portfolio file uploads: file inputs are unsupported by design.
• CAPTCHAs.
• Submit, every time: destructive clicks require your confirmation.
• Sign-ins and passwords: refused fields.

Where Windsurf sits in this series

Functionally the flow matches the rest of the series: Claude Code on Greenhouse, Cursor on Lever, Codex CLI on Workday, Gemini CLI on LinkedIn. Windsurf's distinction is Cascade's narrated multi-step execution: it reads one instruction and walks the whole plan, which suits people who prefer supervising a sequence over issuing steps. Token usage is the same near-zero story everywhere: finding is local, so the model only pays for reading and drafting.

FAQ

Does Windsurf support MCP servers like this?

Yes, via mcp_config.json; Dowser registers as a stdio server and Cascade sees the five dowser tools.

Can Cascade run several applications in a row?

Yes: queue postings in tabs and say "next". Each application's context is small (no snapshots), so long sessions stay coherent.

What breaks on unusual boards?

Custom canvas widgets or wholly unlabelled fields drop match confidence; Dowser then returns candidates instead of guessing, and Cascade asks you. Standard boards (Ashby, Greenhouse, Lever, Workday) resolve cleanly.

Is my data safe?

The page is processed locally by the extension; your profile lives in your Windsurf conversation or your own file. Dowser has no server and nothing to send data to.

Cost of the whole stack?

Your existing Windsurf plan plus Dowser at $29 once after the 5-day trial. No per-action costs, by design.