Marketing Email Automation

EMAIL AUTOMATION — WORKFLOW OS (OPERATIONAL)

Built as a no-fluff execution skill for email marketing automation across B2B and B2C.

Structure: Core email automation fundamentals first. Platform-specific setup in dedicated sections. AI personalization in clearly labeled "Optional: AI / Automation" sections.

Modern Best Practices (January 2026)

• HubSpot Email: https://knowledge.hubspot.com/email/
• Klaviyo Help: https://help.klaviyo.com/
• Mailchimp Resources: https://mailchimp.com/resources/
• Google Sender Guidelines: https://support.google.com/mail/answer/81126

When to Use This Skill

• Workflow design: Trigger-based sequences, nurture flows, lifecycle emails
• Platform setup: HubSpot, Klaviyo, Mailchimp, Braze configuration
• Segmentation: List management, behavioral segments, RFM models
• Deliverability: Authentication, warm-up, reputation management
• Personalization: Dynamic content, merge tags, conditional logic

Core: Email Workflow Types

Core: Workflow Design Framework

Workflow Blueprint Template

WORKFLOW: [Name]
TRIGGER: [Event that starts flow]
GOAL: [Primary conversion action]
DURATION: [Total time span]

┌─────────────────────────────────────────────────────────────┐
│                      ENTRY CRITERIA                          │
│  Trigger: [Event]                                           │
│  Filters: [Conditions to enter]                             │
│  Exclusions: [Who NOT to include]                           │
└─────────────────────────────────────────────────────────────┘
                              │
                              ▼
┌─────────────────────────────────────────────────────────────┐
│  EMAIL 1: [Name]                                            │
│  Delay: Immediate / [X hours/days]                          │
│  Subject: [Subject line]                                    │
│  Goal: [Micro-conversion]                                   │
│  CTA: [Primary action]                                      │
└─────────────────────────────────────────────────────────────┘
                              │
                              ▼
┌─────────────────────────────────────────────────────────────┐
│  WAIT: [X days] or UNTIL [condition]                        │
└─────────────────────────────────────────────────────────────┘
                              │
                              ▼
┌─────────────────────────────────────────────────────────────┐
│  BRANCH: IF [condition]                                     │
│  ├─ YES → [Next step for engaged]                          │
│  └─ NO → [Next step for non-engaged]                       │
└─────────────────────────────────────────────────────────────┘
                              │
                              ▼
┌─────────────────────────────────────────────────────────────┐
│  EXIT CRITERIA                                              │
│  Goal met: [Conversion action]                              │
│  Unsubscribe: Remove from flow                              │
│  Time limit: [Max days in flow]                             │
└─────────────────────────────────────────────────────────────┘

Core: Standard Workflow Templates

1. Welcome Sequence (4 emails, 7 days)

TRIGGER: New subscriber
GOAL: First purchase / demo booking

Email 1 (Immediate): Welcome + Value Prop
├─ Subject: "Welcome to [Brand] - here's what's next"
├─ Content: Brand story, what to expect, quick win
└─ CTA: [Primary action based on business]

WAIT: 2 days

Email 2 (Day 2): Problem Agitation
├─ Subject: "The [problem] most [audience] face"
├─ Content: Pain point, consequences, hint at solution
└─ CTA: Read guide / Watch video

WAIT: 2 days

Email 3 (Day 4): Social Proof
├─ Subject: "How [Customer] achieved [Result]"
├─ Content: Case study, testimonial, results
└─ CTA: See more stories / Book demo

WAIT: 3 days

Email 4 (Day 7): Soft Sell
├─ Subject: "Ready to [achieve outcome]?"
├─ Content: Offer summary, urgency, risk reversal
└─ CTA: Start trial / Book demo / Buy now

2. Abandoned Cart (3 emails, 72 hours)

TRIGGER: Cart created, no purchase in 1 hour
GOAL: Complete purchase

Email 1 (1 hour): Reminder
├─ Subject: "You left something behind"
├─ Content: Cart contents, product images
└─ CTA: Complete order (direct to cart)

WAIT: 24 hours
IF: Still not purchased

Email 2 (Day 1): Urgency + Support
├─ Subject: "Your cart is waiting (questions?)"
├─ Content: Cart contents, FAQ, support link
└─ CTA: Complete order + Chat with us

WAIT: 48 hours
IF: Still not purchased

Email 3 (Day 3): Incentive (optional)
├─ Subject: "10% off to complete your order"
├─ Content: Discount code, expiration
└─ CTA: Use code [CODE] - Shop now

EXIT: Purchase complete or Day 7

3. Lead Nurture (6 emails, 4 weeks)

TRIGGER: Lead captured (gated content, webinar, etc.)
GOAL: SQL / Demo booking

Email 1 (Immediate): Deliver value
├─ Subject: "Your [resource] is ready"
├─ Content: Download link, quick intro
└─ CTA: Download now

WAIT: 3 days

Email 2 (Day 3): Educational content
├─ Subject: "3 ways to [solve problem]"
├─ Content: Tips, how-to, best practices
└─ CTA: Read full guide

WAIT: 4 days

Email 3 (Day 7): Case study
├─ Subject: "How [Company] achieved [Result]"
├─ Content: Customer story, metrics
└─ CTA: Read case study

WAIT: 5 days

Email 4 (Day 12): Objection handling
├─ Subject: "Worried about [common objection]?"
├─ Content: Address concerns, proof points
└─ CTA: See how we handle [objection]

WAIT: 5 days

Email 5 (Day 17): Comparison/evaluation
├─ Subject: "How we compare to [alternative]"
├─ Content: Comparison, differentiators
└─ CTA: See comparison

WAIT: 7 days

Email 6 (Day 24): Soft close
├─ Subject: "Ready to talk?"
├─ Content: Recap value, offer conversation
└─ CTA: Book a call

BRANCH after each email:
├─ Engaged (opened/clicked) → Continue sequence
├─ Converted (booked demo) → Exit to sales
└─ Unengaged (no opens 3+ emails) → Move to re-engagement

4. Onboarding (5 emails, 14 days)

TRIGGER: New customer / trial start
GOAL: Activation (key feature used)

Email 1 (Immediate): Getting started
├─ Subject: "Welcome! Let's get you set up"
├─ Content: Quick start steps, first action
└─ CTA: Complete setup

WAIT: 1 day
IF: Setup not complete

Email 2 (Day 1): Setup reminder
├─ Subject: "Need help getting started?"
├─ Content: Setup guide, support resources
└─ CTA: Complete setup / Chat with us

WAIT: 2 days

Email 3 (Day 3): Key feature intro
├─ Subject: "Unlock [key feature]"
├─ Content: Feature benefit, how-to
└─ CTA: Try [feature] now

WAIT: 4 days

Email 4 (Day 7): Progress check
├─ Subject: "You're making progress!"
├─ Content: What they've done, next steps
└─ CTA: [Next milestone action]

WAIT: 7 days

Email 5 (Day 14): Value realization
├─ Subject: "[Name], here's what you've achieved"
├─ Content: Usage stats, value delivered
└─ CTA: Upgrade / Continue / Share feedback

BRANCH by activation:
├─ Activated → Success path (upsell)
└─ Not activated → Risk path (support outreach)

Core: Segmentation Framework

Behavioral Segments

RFM Segmentation (E-commerce)

Lifecycle Segments

Core: Email Best Practices

Subject Lines

Do:

• Keep under 50 characters
• Personalize when relevant (name, company)
• Use numbers and specifics
• Create curiosity or urgency
• A/B test consistently

Avoid:

• ALL CAPS
• Excessive punctuation!!!
• Spam trigger words (FREE, ACT NOW)
• Misleading subjects
• Generic subjects ("Newsletter #47")

Email Copy

Structure:

1. Hook (first line): Grab attention, reference pain/benefit
2. Body (2-3 short paragraphs): Value, proof, bridge to CTA
3. CTA (clear, single action): Button or linked text
4. P.S. (optional): Reinforce urgency or secondary offer

Formatting:

• Short paragraphs (2-3 sentences max)
• Plenty of white space
• Mobile-first design (single column)
• One primary CTA per email
• Plain text alternative

Timing

Core: Deliverability Checklist

Authentication (Required)

• SPF configured (RFC 7208)
• DKIM configured (RFC 6376)
• DMARC configured (RFC 7489)
• Custom sending domain (not @gmail.com)

List Hygiene

• Double opt-in enabled (or single with clear consent)
• Unsubscribe link in every email
• Hard bounces removed immediately
• Soft bounces removed after 3 attempts
• Inactive subscribers suppressed (90 days no engagement)
• Spam complaints monitored (<0.1% rate)

Sending Practices

• Consistent sending frequency
• Gradual volume increases (warm-up)
• No purchased lists (ever)
• Engagement-based sending (engaged first)
• Sunset policy for unengaged

Monitoring

Platform Setup Guides

HubSpot

See resources/hubspot-setup.md

Klaviyo

See resources/klaviyo-setup.md

Mailchimp

See resources/mailchimp-setup.md

Quick Reference

Decision Tree (Email Triage)

Open rates low (<15%)?
├─ Check sender reputation (Google Postmaster, MXToolbox)
├─ Check subject lines (A/B test)
├─ Check send time (test different times)
└─ Check list quality (remove inactive)

Click rates low (<1%)?
├─ Check content relevance (segmentation)
├─ Check CTA clarity (single, prominent)
├─ Check mobile rendering (responsive design)
└─ Check email length (shorter often better)

High unsubscribes (>0.5%)?
├─ Check frequency (too often?)
├─ Check relevance (right content to right segment?)
├─ Check expectations (did they know what they signed up for?)
└─ Add preference center (let them choose frequency/topics)

Deliverability issues?
├─ Check authentication (SPF, DKIM, DMARC)
├─ Check blacklists (MXToolbox)
├─ Check content (spam words, link ratio)
└─ Check sending patterns (consistent volume)

Metrics & KPIs

Primary Metrics

Workflow Metrics

Templates

Anti-Patterns

Optional: AI / Automation

Note: Core email automation fundamentals above work without AI. This section covers optional AI capabilities.

AI Personalization

AI Best Practices

• Always A/B test AI-generated vs human-written
• Review AI content for brand voice consistency
• Use AI for variants, not strategy
• Monitor performance vs control

Related Skills

• marketing-leads-generation — Lead capture and sequences
• marketing-content-strategy — Content for emails
• marketing-cro — Landing page optimization
• startup-go-to-market — Channel strategy

Usage Notes (Claude)

• Stay operational: return workflow diagrams, email copy templates, setup steps
• Include timing recommendations and branching logic
• Always include deliverability requirements (authentication, hygiene)
• Reference platform-specific features when applicable
• Do not invent benchmark data; use ranges or state "varies by industry"