How to use Claude or Cursor to apply to jobs like a pro

TLDR: if you need an agent to handle your job hunting, feed this article to Claude or Cursor and get started today.

Joy De Medici · September 16, 2026

Applying to jobs is a part-time job. Recruiters already run AI over the pile. If you are still doing this by hand, you are not being careful — you are getting lost in a stack of applications written by models.

You NEED an agent that applies for you. If you don't have one, you are behind.

I stopped treating this as a prompting problem. I installed hiair-cli, dropped the skill into Claude or Cursor, and let the agent work against a real profile on hiair.ai.

One thing, in case you skim: you can do this whole thing in Claude or Cursor. If you use Owlbert — that's our agent, on hiair.ai — the token bill is cheaper. Same CLI. Same applications. Owlbert just doesn't burn a general-purpose chat meter to do a job it was built for. Use Claude or Cursor if that's what's already open. Switch to Owlbert when you start doing this every night.

Install the CLI

You need Python 3.11+ and Chrome. Then:

uv tool install hiair-cli
pipx install hiair-cli
hiair login

hiair login prints a short code and opens the browser so you can tie this computer to your account. On a Mac it asks if you want the login worker. Say yes unless you like leaving a terminal open. You can install it later with hiair service install.

If something is wrong, ask Claude or Cursor to run hiair doctor and debug the issue.

Applications fill in your Chrome. Not some browser in a data center. That's the point of pairing.

Then give Claude or Cursor the skill

hiair skill install --client cursor --global
hiair skill install --client claude --global

Or run hiair skill install and pick from the list. After that, you can say things like "what are my top matches" or "queue the Anthropic one" without teaching the agent our flags. After a CLI update, run the install again so the skill isn't stale.

What happens after you hit apply

Queue from hiair.ai or from the agent. The worker (or hiair apply in a terminal) opens Chrome and fills the form. If the page wants a login, a captcha, or an answer the agent does not know, it stops and asks you. You answer once. It writes that into memory. Next time that question shows up, it already knows your case — the more you talk to it, the more it is tailored to you. The other tabs keep going.

Every run shows up in the tracker on hiair.ai: what you sent, what you answered, where it stands. Connect your email and the agent keeps that tracker in sync. Confirmations, next steps, the rejections — filed on the right application, so you are not opening twenty "we've decided to move forward with other candidates" emails at midnight. That inbox will wreck a week. Let the agent take it.

That's really the whole thing

Account on hiair.ai. hiair-cli, hiair login, skill into Claude or Cursor. Ask for matches. Queue the ones you'd actually take. Watch the tracker instead of refreshing Workday at 11pm.

You will still get rejected. Nobody has a model for that. What you won't do is lose the thread of what you sent, what they asked, and what they wrote back.

Claude or Cursor can run it. Owlbert is cheaper if you're going to live in this.