Skills
skills/dvorkinguy/claude-skills-agents/cold-email-outreach

cold-email-outreach

SKILL.md

Cold Email Outreach

When to Use

  • Setting up cold email campaigns that feed leads into Attio
  • Designing email sequences with follow-ups
  • Configuring Smartlead campaigns and webhooks
  • Setting up sending infrastructure (domains, mailboxes)
  • Integrating cold email replies with CRM via n8n
  • A/B testing subject lines and email copy
  • Building AI-personalized outreach at scale

Recommended Stack

Component Tool Cost
Sequencing Smartlead $39/mo (base: 6,000 emails/mo, 2,000 active contacts)
Domains Cloudflare Registrar ~$10/domain/year
Mailboxes SmartSenders $4.50/mailbox/month
Enrichment Apify + Perplexity (via OpenRouter) ~$0.01/lead
AI Personalization Gemini Flash (via OpenRouter) ~$0.001/email
CRM Attio (via n8n webhook) included

Sending Infrastructure Setup

Domain Strategy

Buy separate sending domains per brand to protect your main domains. Never send cold email from your primary domain.

Brand Primary Domain Sending Domains
guydvorkin.com guydvorkin.com guydvorkin.co, guydvorkin.io, gdvorkin.com
exportarena.com exportarena.com exportarena.co, exportarena.io, exparena.com
afarsemon.com afarsemon.com afarsemon.co, afarsemon.io, afarsemon.net
cranianity.com cranianity.com cranianity.co, cranianity.io, cranianity.net

Mailbox Setup (per sending domain)

3 mailboxes per domain, each sending max 30 emails/day:

guy@guydvorkin.co
hello@guydvorkin.co
team@guydvorkin.co

Total per brand: 3 domains x 3 mailboxes = 9 mailboxes = 270 emails/day = ~8,100/month

DNS Configuration (per sending domain)

Set these records in Cloudflare for each sending domain:

SPF:  TXT  @  "v=spf1 include:smartsenders.io ~all"
DKIM: TXT  (provided by SmartSenders after mailbox creation)
DMARC: TXT _dmarc  "v=DMARC1; p=none; rua=mailto:dmarc@yourdomain.com"
MX:   MX   @  (provided by SmartSenders)

Warmup Protocol

  1. Add all mailboxes to Smartlead warmup pool
  2. Warmup for 14 days minimum before sending campaigns
  3. Start at 5 emails/day, ramp up by 3/day
  4. Target warmup settings: 30-40 emails/day, 30% reply rate
  5. Keep warmup running even during active campaigns

Email Sequence Template

4-Step AI Workforce Outreach Sequence

Step 1: Initial Outreach (Day 0)

Subject A: {{first_name}}, quick question about {{company}}'s workflow Subject B: AI is changing {{industry}} - here's how

Hi {{first_name}},

{{ai_personalized_first_line}}

We help companies like {{company}} automate repetitive workflows using AI agents -- think of it as hiring a digital workforce that works 24/7 without the overhead.

One of our clients in {{industry}} cut their manual processing time by 70% in the first month.

Worth a 15-min call to see if something similar could work for {{company}}?

Best,
{{sender_name}}
{{brand}}

Step 2: Value-Add Follow-Up (Day 3)

Subject: Re: {{previous_subject}}

Hi {{first_name}},

Wanted to share a quick example that might be relevant.

We recently helped a {{industry}} company automate their {{pain_point_area}} process. The result: what used to take their team 20 hours/week now runs automatically.

The ROI broke even in week 2.

Happy to walk you through how it could work for {{company}} -- no pressure, just showing you what's possible.

{{sender_name}}

Step 3: Social Proof (Day 8)

Subject: Re: {{previous_subject}}

Hi {{first_name}},

I know you're busy, so I'll keep this short.

Here's what {{similar_company}} said after 3 months with our AI Workforce:

"We eliminated 2 full-time positions worth of manual data entry and redirected that budget to growth."

If {{company}} has any processes that feel repetitive or bottlenecked, that's exactly what we solve.

Open to a quick chat this week?

{{sender_name}}

Step 4: Break-Up (Day 15)

Subject: Should I close your file, {{first_name}}?

Hi {{first_name}},

I've reached out a few times and haven't heard back -- totally understand if the timing isn't right.

I'll assume this isn't a priority for {{company}} right now and won't follow up again.

But if AI automation is ever on your radar, just reply to this email and I'll be here.

All the best,
{{sender_name}}

Personalization Variables

Variable Source How to Get
{{first_name}} Lead list CSV import
{{company}} Lead list CSV import
{{industry}} Enrichment Apify company data
{{ai_personalized_first_line}} AI Gemini Flash via OpenRouter
{{pain_point_area}} Enrichment Perplexity research
{{similar_company}} Manual Match to case study
{{sender_name}} Campaign config Per brand
{{brand}} Campaign config Per brand

AI First-Line Personalization (via n8n)

Use the enrichment sub-workflow output to generate a personalized opening line:

{
  "type": "@n8n/n8n-nodes-langchain.openAi",
  "parameters": {
    "model": "google/gemini-2.5-flash-preview",
    "baseUrl": "https://openrouter.ai/api/v1",
    "prompt": "Write a personalized first line for a cold email to {{first_name}} at {{company}}. Use this research:\n\n{{enrichment_summary}}\n\nRules:\n- One sentence only\n- Reference something specific about their company or role\n- Sound natural, not salesy\n- No generic compliments\n- Connect to AI/automation if possible",
    "options": {
      "temperature": 0.7,
      "maxTokens": 100
    }
  }
}

Smartlead Configuration

Campaign Settings

Daily send limit per mailbox: 30
Time between emails: 8-15 minutes (randomized)
Sending window: 8am-6pm recipient timezone
Track opens: Yes
Track clicks: Yes
Stop on reply: Yes
Stop on auto-reply: No (filter auto-replies separately)

Smartlead API Integration (for n8n)

Base URL: https://server.smartlead.ai/api/v1

Create Campaign:

curl -X POST "https://server.smartlead.ai/api/v1/campaigns/create?api_key=$SMARTLEAD_API_KEY" \
  -H "Content-Type: application/json" \
  -d '{
    "name": "Q1 Export Arena - Manufacturing AI",
    "timezone": "America/New_York"
  }'

Add Leads to Campaign:

curl -X POST "https://server.smartlead.ai/api/v1/campaigns/$CAMPAIGN_ID/leads?api_key=$SMARTLEAD_API_KEY" \
  -H "Content-Type: application/json" \
  -d '{
    "lead_list": [
      {
        "email": "john@acme.com",
        "first_name": "John",
        "last_name": "Doe",
        "company": "Acme Corp",
        "custom_fields": {
          "industry": "Manufacturing",
          "ai_first_line": "Saw Acme just expanded their logistics team..."
        }
      }
    ]
  }'

Get Campaign Stats:

curl "https://server.smartlead.ai/api/v1/campaigns/$CAMPAIGN_ID/analytics?api_key=$SMARTLEAD_API_KEY"

Smartlead Webhook Events

Configure webhooks in Smartlead Settings to POST to your n8n webhook:

Event Webhook Payload Key CRM Action
REPLY event_type: "REPLY" sequence_status=Replied, lead_temperature=Hot, lead_score+=30
OPEN event_type: "OPEN" lead_temperature=Warm (if Cold), lead_score+=5
CLICK event_type: "CLICK" lead_temperature=Warm, lead_score+=10
BOUNCE event_type: "BOUNCE" sequence_status=Paused, lead_score=0
UNSUBSCRIBE event_type: "UNSUBSCRIBE" sequence_status=Completed, add note

Webhook Payload Example (Reply)

{
  "event_type": "REPLY",
  "email": "john@acme.com",
  "first_name": "John",
  "last_name": "Doe",
  "campaign_id": 12345,
  "campaign_name": "Q1 Export Arena - Manufacturing AI",
  "reply_text": "Thanks for reaching out. Can we schedule a call next week?",
  "reply_date": "2026-03-01T14:30:00Z"
}

CRM Integration Flow

Smartlead Webhook to n8n to Attio

Smartlead Event → n8n Webhook (POST /smartlead-events)
  → Switch on event_type
    → REPLY:
        1. search_records (people, email)
        2. update_record: sequence_status=Replied, lead_temperature=Hot, lead_score+=30
        3. create_note: "Replied to cold email campaign: {campaign_name}. Reply: {reply_text}"
        4. Telegram notification: "Hot lead reply from {name}!"
    → OPEN:
        1. search_records (people, email)
        2. update_record: lead_score+=5, lead_temperature=Warm (if currently Cold)
    → CLICK:
        1. search_records (people, email)
        2. update_record: lead_score+=10, lead_temperature=Warm
    → BOUNCE:
        1. search_records (people, email)
        2. update_record: sequence_status=Paused, lead_score=0
        3. create_note: "Email bounced in campaign: {campaign_name}"
    → UNSUBSCRIBE:
        1. search_records (people, email)
        2. update_record: sequence_status=Completed
        3. create_note: "Unsubscribed from campaign: {campaign_name}"

n8n Workflow Node Structure

[Webhook Trigger] → [Switch: event_type]
  → [HTTP Request: Attio search] → [HTTP Request: Attio update] → [Telegram notify]

A/B Testing Strategy

Test these elements in order of impact:

  1. Subject lines (biggest impact on open rate)

    • Test 2 variants per step, 50/50 split
    • Winner after 200+ sends with statistical significance
    • Target: 40%+ open rate

  2. First line (impact on reply rate)

    • AI-personalized vs template-based
    • Target: 3-5% reply rate

  3. CTA (impact on conversion)

    • "15-min call" vs "quick question" vs "send you a case study"

  4. Sequence length

    • 3 steps vs 4 steps vs 5 steps

Campaign Checklist

  • Sending domains purchased and DNS configured
  • Mailboxes created in SmartSenders (3 per domain)
  • Mailboxes added to Smartlead and warmup started (14+ days)
  • Lead list enriched with company data and AI first lines
  • Email copy written with A/B subject lines
  • Smartlead campaign created with correct sending settings
  • Smartlead webhooks configured to POST to n8n
  • n8n workflow deployed: Smartlead webhook to Attio sync
  • Test webhook payload sent and verified in Attio
  • Brand-specific sender signature configured

Cost Breakdown (per brand)

Item Monthly Cost
Smartlead (shared across brands) $39 / 4 = ~$10
3 sending domains $30/year = $2.50
9 mailboxes ($4.50 each) $40.50
Enrichment (~200 leads) ~$2
AI personalization ~$0.20
Total per brand ~$55/month

References

  • See docs/guides/cold-email/ for tool-specific documentation
  • See docs/skills/n8n-crm-workflows.md for workflow #8 (Cold Email Sequencer)
  • See docs/skills/attio-crm-setup.md for CRM field definitions
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