Send HR Outreach Email

Send a personalised cold outreach email with resume + portfolio attached using send_outreach_emails.py.

Script location

claude-job-agent\send_outreach_emails.py

What you need from the user

If the user hasn't provided all required info, ask for it before running.

Steps

1 — Preview first (dry run to user's inbox)

Always send a test to your own address (recipient_email in config.py) first so the user can approve the email:

cd claude-job-agent
echo yes | python send_outreach_emails.py --name "[NAME]" --email "[email protected]" --company "[COMPANY]"

Show the preview output to the user and ask: "Looks good? Send to the real recipient?"

2 — Send to real recipient (only after user confirms)

cd claude-job-agent
echo yes | python send_outreach_emails.py --name "[NAME]" --email "[EMAIL]" --company "[COMPANY]"

Add --cc "[CC_EMAIL]" if a CC was provided.

What the script does automatically

• Looks up the role from List.xlsx (matches company name, status = done)
• If found in tracker (role known/overridden) → status=done means already applied, so it uses email_followup_template.txt ("I recently applied for the {role} role...") — never the agency-flavored cold outreach template
• If not in tracker → sets role to [Company] opportunities and uses email_cold_outreach_spontaneous_template.txt
• Attaches both PDFs from resume/ folder
• Shows full preview before sending

Rules

• Never skip the test send step — always preview to user's inbox first
• Never send to real recipient without explicit user approval after the test
• If the script errors on missing attachment, check that resume/ folder has both PDFs
• If template not found, check that emailoutreach/email_cold_outreach_template.txt exists
• LinkedIn InMail variants also live in emailoutreach/: linkedinoutreach_followup_template.txt (checking status on an application) and linkedinoutreach_coldintro_template.txt (plain cold outreach, no application)
• Do not hardcode HR contact details anywhere in code or skill files
• If the job listing URL returns 404 or any error (expired/taken down), do not send the outreach email — the role no longer exists. Either switch to the spontaneous template or skip entirely and notify the user.

Weekly draft mode — "send this week's outreach emails"

Per user instruction (2026-08-17): drafts to known/verified HR contacts are sent automatically, no per-email confirmation. This applies to drafts produced by the weekly-hr-search routine, and to any future "draft outreach then send" workflow unless the user says otherwise.

When triggered by "send this week's outreach emails", "send weekly outreach", "send the drafted emails" — or automatically at the end of the weekly-hr-search routine right after drafts are written:

Step 1 — Read saved drafts

Check claude-job-agent\outreach_drafts\ for *_draft.txt files.

Parse each file:

TO: {email}
SUBJECT: {subject}
---
{body}

Step 2 — Send automatically

For each draft, send via send_outreach_emails.py (or an equivalent direct SMTP send of the draft's own SUBJECT/body, which was built from email_followup_template.txt for tracked roles or email_cold_outreach_spontaneous_template.txt otherwise; never email_cold_outreach_template.txt) — no confirmation prompt, no dry-run-to-self step.

Do NOT send, and instead note as skipped in the receipt (see Step 4), if:

• The contact's email is flagged undeliverable/invalid by Hunter (or any verifier). Confirmed 2026-08-17: [email protected] was flagged "undeliverable" by Hunter, sent anyway, and did in fact bounce/get flagged by Netatmo's mail server — so trust the verifier's "invalid/undeliverable" status and skip rather than guess-and-send.
• A guessed email has no verification at all (Hunter wasn't able to check it, e.g. accept-all domain) — still send it, but flag it clearly as unverified in the receipt so the user knows it's a lower-confidence guess. This is different from a confirmed-bad flag above.
• The job listing URL returns 404 or any "no longer available" signal — skip, do not send, note it in the receipt.

Step 3 — Clean up sent drafts

After a draft sends successfully, delete that _draft.txt file so it doesn't appear again next week.

Step 4 — Send a receipt email (mandatory, every run)

After sending (or attempting) all drafts, send a plain-text receipt to your own address (recipient_email in config.py) listing, for every email actually sent:

• Company name
• Role
• HR contact name + email sent to
• Any caveat (e.g. "unverified email, watch for bounce")

And for anything skipped: company, reason skipped.

Fallback — no drafts folder or empty

If outreach_drafts/ doesn't exist or has no draft files, fall back to the standard single-email flow and ask the user for --name, --email, --company.