Build Your Own Job Search Agent

01

How the system works

This is not a script you run manually. It is an autonomous agent that fires at 9am every morning, does its job, and emails you a digest — whether your machine is open or not.

The execution engine is Claude Cowork, Anthropic's desktop tool for running autonomous Claude tasks on a schedule. Each morning the task fires, Cowork loads a plain markdown file called SKILL.md into a fresh Claude session, and Claude runs the full workflow with zero memory from previous runs. Everything it needs is in the file.

No browser tab open. No Terminal window. No manual trigger. Your machine just needs to be awake.

02

What you need first

Four things need to be in place before running anything. All four are required.

Requirement	What it is	Why it is needed
Claude Cowork	Anthropic's desktop agent tool	Runs the scheduled task. Without it there is no execution engine.
Gmail account	The inbox the agent reads and sends from	Agent checks for interview emails and sends your digest from here.
Gmail app password	16-character token from Google settings	Lets Claude send email via SMTP without your real password exposed.
Mac on power	MacBook connected to mains or powered monitor	Task only fires if the machine is awake. Sleep = missed run.
Windows PC on power	PC connected to mains with sleep prevention on	Task only fires if the machine is awake. Sleep = missed run.

ℹYou do not need to know how to code. Every file in this guide is plain text. Every command is copy-paste ready.

How the 5 filters work

Every job found gets passed through all 5 filters in sequence. Fail any one and it is dropped. Only roles that clear all 5 reach your inbox.

01 Location Remote from your country or hybrid your city only

drops US-only →

02 Shift timing Your timezone compatible, no overnight shifts

drops night shifts →

03 Seniority Senior, Lead, Principal, Specialist only

drops junior roles →

04 Role type Internal L&D teams only — no agencies

drops agencies →

05 Blocked companies Your personal no-fly list — hard block

drops blocked →

✓ Only what passes all 5 reaches your inbox

03

Gmail app password

This step is identical on Mac and Windows. Do not use your regular Gmail password — it will not work and it is not secure.

!Never use your actual Gmail password. A Gmail app password is a separate 16-character token that can be revoked at any time without changing your main password.

Enable 2-Step Verification

3.1

App passwords only work when 2FA is active. Go to myaccount.google.com, click Security, and enable 2-Step Verification if it is not already on.

Generate the app password

3.2

Still in myaccount.google.com, use the search bar and search for App passwords. Type Job Agent as the name and click Create. Google shows a 16-character password in groups of four:

abcd efgh ijkl mnop

Copy it immediately. Google only shows it once.

Remove the spaces before saving

3.3

Google adds spaces for readability. Remove them before using it anywhere:

abcdefghijklmnop   # 16 chars, no spaces

✓Keep this ready. You will paste it into a file in the next section. Do not paste it into a chat or shared document.

04

Email config file

The Gmail app password lives in a plain text file on your machine. Claude reads it from disk at runtime — it is never hardcoded in the prompt, never exposed in a log.

Open Terminal and create the file

4.1

Mac

# Create the folder
mkdir -p ~/Downloads/Job\ Search

# Open the config file in nano
nano ~/Downloads/Job\ Search/email_config.txt

Type exactly this inside the file

4.2

Mac

GMAIL_USER=your.email@gmail.com
GMAIL_APP_PASSWORD=abcdefghijklmnop

Replace both values with your actual Gmail address and 16-character app password from Section 3.

Save and exit nano

4.3

Mac

Ctrl+O   # Write the file
Enter    # Confirm filename
Ctrl+X   # Exit nano

Verify the file

4.4

Mac

cat ~/Downloads/Job\ Search/email_config.txt

Both lines should print back. If not, repeat from step 4.1.

Open Notepad

4.1

Windows

Press Win + R, type notepad, and press Enter.

Type exactly this inside Notepad

4.2

Windows

GMAIL_USER=your.email@gmail.com
GMAIL_APP_PASSWORD=abcdefghijklmnop

Replace both values with your actual Gmail address and app password from Section 3.

Save to the right location

4.3

Windows

File → Save As → navigate to Downloads → create a folder called Job Search → save as email_config.txt. Set Save as type to All Files to avoid a .txt.txt double extension. Full path:

C:\Users\YourName\Downloads\Job Search\email_config.txt

Verify in PowerShell

4.4

Windows

Press Win + X → Terminal or PowerShell, then run:

Get-Content "$env:USERPROFILE\Downloads\Job Search\email_config.txt"

Both lines should print back. If not, re-check the save path.

ℹIf this file is missing at runtime, the agent logs a warning and skips sending rather than crashing the whole run.

05

Setting up Cowork

Cowork is Anthropic's desktop tool for running Claude autonomously on a schedule. The setup is the same on Mac and Windows.

Download and install the Claude desktop app

5.1

Go to claude.ai, download the desktop app for your OS, install it, and sign in with your Anthropic account.

Switch to Cowork mode

5.2

Open the Claude desktop app. Look for the Cowork option in the sidebar or via the mode switcher at the top. Switch to it. Cowork is the mode that supports scheduled autonomous tasks.

!Cowork requires Claude Pro or higher. Check your plan at claude.ai/settings before proceeding.

ℹCowork is a beta product. UI labels may differ slightly as Anthropic updates it. If a label does not match this guide exactly, look for anything related to "schedule", "automate", or "task" in the interface — the underlying capability is stable.

06

Connecting Gmail MCP

MCP stands for Model Context Protocol. It gives Claude live access to your Gmail inbox during each run. You authorize it once — it persists on both Mac and Windows.

Open Connectors in Cowork

6.1

Inside Cowork, look for a Connectors or Integrations section in the settings panel. Click Add connector.

Connect Gmail

6.2

Find Gmail in the list and click Connect. A Google OAuth screen will appear. Sign in with the same account your email_config.txt uses. Grant the read permissions.

Confirm the connection

6.3

Gmail should now appear as a connected service in your Cowork connectors list. The agent will use this to search your inbox for application emails from the past 24 hours on every run.

✓This authorization persists until you manually revoke it from your Google account settings. Note: Google may invalidate inactive tokens after several months of no use — if the connection drops after a long break, simply reconnect.

07

Getting Claude to write your SKILL.md

You do not write this file yourself. You open a Claude chat, describe what you want in plain language, and Claude writes the entire SKILL.md for you. Your job is to know what you want clearly enough to describe it.

The SKILL.md is the brain of the agent — a plain markdown file Claude reads cold at the start of every run with no memory from previous days. Everything the agent needs must be in this file. Claude builds it from your description.

Open a new Claude chat

7.1

Go to claude.ai or open the Claude desktop app in standard chat mode (not Cowork). Start a new conversation.

Describe your profile and requirements

7.2

Tell Claude who you are and what you are looking for. Be specific — vague descriptions produce vague filters. Here is a template that works well:

Your message to Claude

I want you to write a SKILL.md file for an autonomous job search agent running in Claude Cowork.

About me:
— [X]+ years in L&D
— Targeting: Senior Instructional Designer, Learning Technologist, Senior LXD, eLearning Developer
— Location: [Your City] — remote or hybrid [Your City] only
— Timezone: [Your timezone] — no overnight shifts
— Core tools: [Your stack — Storyline, xAPI, LMS, etc.]
— Email: your@gmail.com

My hard filters — every job must pass ALL of these:
1. Remote from [Country] or Hybrid [Your City] only
2. [Timezone]-compatible hours only, nothing past [time]
3. Senior, Lead, or Principal titles only — no Analyst or Associate
4. Internal L&D teams only — no agencies, no outsourcing firms
5. Blocked companies: [list any you want excluded]

Job boards to search: Himalayas, Remotive, WeWorkRemotely, Wellfound, Greenhouse, LinkedIn

The agent should check my Gmail inbox daily for interview calls, assessments, and rejections from the last 24 hours.

Credentials file: ~/Downloads/Job Search/email_config.txtC:\Users\YourName\Downloads\Job Search\email_config.txt

Send me a formatted daily email digest with new roles and application updates. Include filter reasoning for rejected roles. Handle failures gracefully — log them, never crash silently.

Iterate until it is right

7.3

Claude will generate the full SKILL.md. Read through it. If anything is wrong — a filter is too loose, a job board is missing, the email format is not what you want — just tell Claude in plain language. It revises immediately.

You are the product manager. Claude is the engineer writing the spec file. Keep going until the file reflects exactly what you want.

Save the file Claude produces

7.4

Once you are happy with it, copy the full SKILL.md content and save it as a plain text file:

~/Downloads/Job Search/SKILL.md

Open TextEdit, paste the content, go to Format → Make Plain Text, then save.

C:\Users\YourName\Downloads\Job Search\SKILL.md

Open Notepad, paste the content, and save as SKILL.md with Save as type set to All Files.

ℹThe reference blocks below show what a complete SKILL.md looks like — not for you to fill in manually, but so you can recognise what Claude builds and give better feedback during your review.

What Claude builds — reference only

SKILL.mdCandidate profile

## Candidate Profile
Name: Your Full Name
Role targets: Senior Learning Experience Designer,
              Learning Technologist, eLearning Developer
Location: [Your City, Country]
Work mode: Remote or Hybrid [Your City] only
Experience: [X]+ years across L&D
Core stack: [Your tools]
Email: your.email@gmail.com

SKILL.mdHard filters

## Hard Filters — ALL must pass

Filter 1 — Location: Remote [Country] OR Hybrid [City] only.
Filter 2 — Shift timing: [Timezone]-compatible only. No overnight.
Filter 3 — Seniority: Senior, Lead, Principal, Specialist only.
  Reject: Analyst, Associate, Coordinator, Intern, Trainee.
Filter 4 — Role type: Internal L&D only.
  Reject: agencies, outsourcing, client-billing models.
Filter 5 — Blocked companies: [List — one per line]

ℹFilter 4 is the most important. Internal L&D means the company has its own team serving its own employees. An agency producing content for external clients fails this filter regardless of the job title.

SKILL.mdSearch, Gmail check, email config, format, failure handling

## Search Instructions
Run all 9 queries. Use WebFetch to read full listing before filtering.
# Queries cover: Himalayas, Remotive, WeWorkRemotely,
# Wellfound, Greenhouse, LinkedIn × multiple role titles

## Gmail Inbox Check
Use Gmail MCP. Search last 24h for: interview, assessment,
application, offer, next steps, unfortunately.
Classify and include in digest under APPLICATION UPDATES.

## Email Config
Read from: ~/Downloads/Job Search/email_config.txtRead from: C:\Users\YourName\Downloads\Job Search\email_config.txt
Use Python SMTP. Subject: Daily Job Search Update — [date] — [N] new roles.
If file missing: log warning, skip sending, continue run.

## Failure Handling
Never fail silently. Log every run to agent_log.txt.
Format: [DATE] [TIME] — Screened: N. Passed: N. Sent: yes/no

✓Once Claude has generated your SKILL.md and you have saved it, you are ready to schedule the task. Keep the file path handy for the next section.

08

Scheduling the task

On Mac, Cowork manages the schedule internally. No Terminal needed for this step.

Create a scheduled task in Cowork

8.1

Mac

Task name:     daily-job-search
Prompt source: ~/Downloads/Job Search/SKILL.md
Schedule:      Daily at 9:00 AM
Connectors:    Gmail MCP  (must be enabled)

Save and activate

8.2

Mac

Save the task. Cowork will fire it daily at your chosen time as long as the Mac is awake and the Claude app is running.

On Windows, Cowork manages the schedule internally. You also need Claude in Startup apps so it launches automatically after any reboot.

Create a scheduled task in Cowork

8.1

Windows

Task name:     daily-job-search
Prompt source: C:\Users\YourName\Downloads\Job Search\SKILL.md
Schedule:      Daily at 9:00 AM
Connectors:    Gmail MCP  (must be enabled)

Add Claude to Startup apps

8.2

Windows

Press Win + I → Apps → Startup → find Claude → toggle On. Without this, a reboot leaves Cowork offline and the task will not fire.

Verify in Task Scheduler (optional)

8.3

Windows

Press Win + S, search Task Scheduler, open it. Look for daily-job-search in the library. Next Run Time should show tomorrow at 9:00 AM.

ℹEach run opens a completely fresh Claude session with no memory from previous days. SKILL.md is the entire context Claude works from.

09

Keeping your machine awake

The scheduled task only fires if the machine is awake. Sleep means a missed run — no catch-up, just a gap in that day's digest.

Prevent sleep on power adapter

9.1

Mac

System Settings → Battery → Options and enable:

Prevent automatic sleeping on power adapter when display is off  ON

This path applies to macOS Ventura (13) and later. On older macOS, find the equivalent in System Preferences → Energy Saver.

Add Claude to Login Items

9.2

Mac

System Settings → General → Login Items → click + → add the Claude desktop app. Cowork starts automatically on every boot.

Clamshell mode with a powered monitor

9.3

Mac

If your external monitor charges the Mac via USB-C Power Delivery, closing the laptop lid keeps the Mac fully awake without fan noise. The Mac draws power from the monitor, stays awake, and the agent fires at 9am regardless. This is the cleanest always-on setup for this workflow.

!On battery only, the Mac may sleep regardless of Battery settings. The agent requires mains power to run reliably overnight.

Disable sleep when plugged in

9.1

Windows

Settings → System → Power and sleep and set:

When plugged in, PC goes to sleep after: Never

This applies to both Windows 10 and Windows 11. The path is the same.

Screen can sleep, PC cannot

9.2

Windows

On the same screen you can allow the display to turn off while keeping the PC awake:

When plugged in, turn off display after: 30 minutes
When plugged in, PC goes to sleep after: Never

The agent fires regardless of whether the display is on or off.

Confirm Claude is in Startup apps

9.3

Windows

Settings → Apps → Startup → confirm Claude is toggled On. A reboot without this leaves Cowork offline and the task will not fire.

!On battery only, Windows may still sleep depending on your power plan. The agent requires mains power to run reliably.

10

Your first run

Before waiting until 9am tomorrow, trigger a manual test run to confirm everything works end to end.

Trigger a manual run in Cowork

10.1

Find your saved task in Cowork and look for a Run now or Test option. Trigger it. Watch the activity panel as Claude works through each step in sequence.

What to expect during the run

10.2

The first run takes longer because Claude fetches each listing URL to read the full description before filtering. Expect 8 to 15 minutes across 9 boards. Subsequent daily runs are faster as fewer new listings appear each day.

Check your inbox

10.3

The digest should arrive within a minute or two of the run completing. If it lands in spam, mark it as not spam and add your own Gmail address to your Contacts — this resolves permanently within one or two runs.

Check the log file

10.4

cat ~/Downloads/Job\ Search/agent_log.txt

Open PowerShell and run:

Get-Content "$env:USERPROFILE\Downloads\Job Search\agent_log.txt"

A timestamped entry should confirm: roles screened, roles passed, email sent yes/no.

11

What the email looks like

A representative example of the digest you receive each morning. This uses sanitized data — not real applications or companies.

Daily Job Search Update

April 20, 2026 · 2 new roles found

Boards: 9 · Screened: 34 · Passed: 2 · Filtered: 32

Application Updates (last 24h)

ACME CORPInterview Scheduled HIGH

RoleSenior Learning Experience Designer

Date and TimeApril 22, 2026 at 11:00 AM IST

ContactPriya Sharma (Recruiter)

GLOBALBANKAssessment Pending ACTION

ActionComplete assessment — check inbox from careers@globalbank.com

New Roles Found: 2

TechCorpSenior LXD — Remote PASSED

FiltersAll 5 passed · Internal L&D team confirmed

URLhimalayas.app/jobs/techcorp-senior-lxd

GlobalBank GCCLearning Technologist — Hybrid PASSED

FiltersAll 5 passed · GCC internal team confirmed

URLgreenhouse.io/globalbank/learning-technologist

Why 32 roles were filtered out

Not remote eligible11 roles

Agency / outsourcing8 roles

Seniority too low6 roles

Customer-facing L&D5 roles

Listing closed2 roles

12

Troubleshooting

No email received after a run

Fix

Check the log file first (Section 10). If it shows "Sent: no", the SMTP step failed. Most likely the Gmail app password in email_config.txt has spaces, is wrong, or the file path is incorrect. Re-check Section 4.

Email arrives but lands in spam

Fix

Gmail sometimes flags self-addressed SMTP email. Open it in spam, click Not spam, and add your own address to Google Contacts. Resolves permanently within one or two runs.

Scheduled task did not fire at 9am

Fix

Mac

Almost always because the Mac was asleep or Cowork was not running. Confirm System Settings → Battery → Options has sleep prevention enabled. Confirm Claude is in Login Items. The task will fire correctly from tomorrow.

Scheduled task did not fire at 9am

Fix

Windows

Confirm the PC was not asleep. Confirm Settings → Power and sleep → sleep is set to Never when plugged in. Confirm Claude is in Startup apps. Open Task Scheduler and check Last Run Time — if it shows never, re-create the task in Cowork.

Gmail MCP shows as disconnected

Fix

Go to Cowork → Connectors and reconnect Gmail. The OAuth token may have expired or been revoked — Google can invalidate tokens after extended inactivity (several months). Re-authorize using the same Google account. Takes under two minutes.

Too many irrelevant roles passing the filters

Fix

Open a new Claude chat, paste your current SKILL.md, and ask Claude to tighten Filter 4. Tell it which types of roles are slipping through. Also add specific agency names to Filter 5. Claude will rewrite the relevant sections — save the updated file and the next run will use the tighter criteria.

Gmail app password stopped working

Fix

App passwords are invalidated if you change your main Google password, disable 2FA, or revoke them manually. Go to myaccount.google.com, generate a new app password named "Job Agent", remove the spaces, update email_config.txt, and the next run picks it up automatically.

How the system works

What you need first

How the 5 filters work

Gmail app password

Enable 2-Step Verification

Generate the app password

Remove the spaces before saving

Email config file

Open Terminal and create the file

Type exactly this inside the file

Save and exit nano

Verify the file

Open Notepad

Type exactly this inside Notepad

Save to the right location

Verify in PowerShell

Setting up Cowork

Download and install the Claude desktop app

Switch to Cowork mode

Connecting Gmail MCP

Open Connectors in Cowork

Connect Gmail

Confirm the connection

Getting Claude to write your SKILL.md

Open a new Claude chat

Describe your profile and requirements

Iterate until it is right

Save the file Claude produces

What Claude builds — reference only

Scheduling the task

Create a scheduled task in Cowork

Save and activate

Create a scheduled task in Cowork

Add Claude to Startup apps

Verify in Task Scheduler (optional)

Keeping your machine awake

Prevent sleep on power adapter

Add Claude to Login Items

Clamshell mode with a powered monitor

Disable sleep when plugged in

Screen can sleep, PC cannot

Confirm Claude is in Startup apps

Your first run

Trigger a manual run in Cowork

What to expect during the run

Check your inbox

Check the log file

What the email looks like

Troubleshooting

No email received after a run

Email arrives but lands in spam

Scheduled task did not fire at 9am

Scheduled task did not fire at 9am

Gmail MCP shows as disconnected

Too many irrelevant roles passing the filters

Gmail app password stopped working

Questions about the setup?

Build a Job Search Agent That Runs While You Sleep

Ready to automate your job search?