outreach-sender

name	outreach-sender
description	Send outreach emails and manage follow-up sequences. Bridges cold-email drafting → humanizer polish → CEO Telegram approval → Gmail send. Tracks sends in pipeline.json. For writing email copy, see cold-email. For lifecycle/nurture emails, see email-sequence.
user-invocable	true

[YOUR_PRODUCT] Context

Before sending, read MEMORY.md for: current wedge, value proposition. Read memory/pipeline.json for prospect context and outreach history. Output in Russian (email content in English unless specified). For chat platforms: show draft for approval, compact format.

Outreach Sender

Orchestrates the full outreach flow: draft → polish → approve → send → track → follow-up.

Outreach Flow (HITL — Human In The Loop)

1. Draft         → cold-email skill writes email based on signal + prospect context
2. Polish        → humanizer skill removes AI patterns
3. Present       → Show draft to CEO in Telegram for approval
4. Approve/Edit  → CEO approves, edits, or rejects
5. Send          → Gmail via Orth OAuth
6. Track         → Record in pipeline.json
7. Schedule      → Set next follow-up date

Step 1: Draft Email

Use cold-email skill with prospect context:

• Signal that triggered outreach (from pipeline.json)
• Company context (from company-intel enrichment)
• Contact info (from lead-enrichment)
• Choose framework based on signal type:
  • Funding → "Trigger > Insight > Ask"
  • Hiring → "Observation > Problem > Proof > Ask"
  • Pain language → "Question > Value > Ask"
  • Competitor mention → "Story > Bridge > Ask"

Step 2: Polish

Run through humanizer skill to remove AI patterns. Critical for cold email credibility.

Step 3: Present for Approval

Format for Telegram:

Outreach Draft #[N]:

To: [Name] ([Title] @ [Company])
Signal: [type] — [detail]
Score: [FIT+INTENT+TIMING total]

Subject: [subject line]

[email body]

Reply:
 approve — send as-is
 edit: [your changes] — I'll update and re-present
 skip — skip this prospect
 later — defer to tomorrow

Step 4: Send via Gmail

After CEO approval:

orth run gmail /send-email --body '{
  "recipient_email": "[e-mail]",
  "subject": "subject line",
  "body": "email body (plain text)"
}'

Step 5: Track in Pipeline

Update prospect in pipeline.json:

{
  "outreach": [{
    "type": "email",
    "date": "2026-03-28T10:00:00Z",
    "subject": "subject line",
    "status": "sent",
    "template": "trigger-insight-ask",
    "signal_type": "funding"
  }],
  "stage": "outreach_sent",
  "next_action": {
    "type": "follow_up_1",
    "date": "2026-03-31T10:00:00Z",
    "detail": "Follow-up #1 — new angle (case study)"
  }
}

Step 6: Follow-Up Cadence

Day	Follow-Up	Angle	Action
0	Initial email	Signal + pain + value	CEO approves
3	Follow-up #1	Case study or data point	Draft → approve → send
5	Follow-up #2	Useful resource or insight	Draft → approve → send
7	Follow-up #3	Social proof (similar company)	Draft → approve → send
10	Breakup email	Respect + door open	Draft → approve → send

Rules:

• Each follow-up adds NEW value — never "just checking in"
• If reply at any point → exit sequence, notify CEO, update stage to meeting_booked or nurture
• If bounce → mark email invalid, try alternate contact via find-email-by-name
• If CEO says "skip" → move to nurture
• After breakup email → move to nurture, re-score in 30 days

Daily Follow-Up Check (Cron Mode)

When triggered by daily cron:

1. Read pipeline.json
2. Find all prospects where next_action.date ≤ today
3. For each due follow-up: a. Draft next email in sequence (using previous outreach context) b. Present to CEO for approval
4. Report: "[N] follow-ups due today: [Company1], [Company2], ..."

Batch Mode

When CEO says "send all approved drafts" or when multiple outreach items are ready:

1. List all approved-but-unsent drafts
2. Send each via Gmail with 30-second delay between sends
3. Update pipeline.json for each
4. Report: "Sent [N] emails. Next follow-ups scheduled."

Reply Handling

When CEO reports a reply:

1. Update prospect stage (meeting_booked, nurture, or closed_lost)
2. Cancel remaining follow-ups in sequence
3. If meeting intent: trigger meeting-prep skill
4. Log via structured-log

Related Skills

• cold-email — writes the email drafts
• humanizer — polishes drafts to remove AI patterns
• email-sequence — for lifecycle/nurture sequences (not cold outreach)
• pipeline-manager — stores all outreach tracking data
• founder-sales — overall sales strategy
• find-email-by-name — fallback for bounced emails