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)
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
| Workflow Type |
Trigger |
Purpose |
Timeline |
| Welcome |
New subscriber |
Introduce brand, set expectations |
Day 0-7 |
| Onboarding |
New customer |
Drive activation, reduce churn |
Day 0-30 |
| Nurture |
Lead capture |
Educate, build trust, convert |
Weeks 1-8 |
| Abandoned Cart |
Cart created, no purchase |
Recover revenue |
Hours 1-72 |
| Re-engagement |
Inactive subscriber |
Win back or clean list |
Day 30-90 |
| Upsell/Cross-sell |
Purchase complete |
Increase LTV |
Day 7-30 post-purchase |
| Renewal/Retention |
Subscription nearing end |
Prevent churn |
Day -30 to -1 |
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
| Segment |
Definition |
Use For |
| Engaged |
Opened/clicked in last 30 days |
Primary campaigns |
| Active |
Logged in / used product recently |
Onboarding, upsell |
| At-risk |
No engagement 31-60 days |
Re-engagement |
| Dormant |
No engagement 61-90 days |
Win-back |
| Churned |
No engagement 90+ days |
Sunset or remove |
RFM Segmentation (E-commerce)
| Segment |
Recency |
Frequency |
Monetary |
Strategy |
| Champions |
Recent |
Often |
High |
Reward, refer |
| Loyal |
Recent |
Often |
Medium |
Upsell |
| Potential |
Recent |
Rare |
Low |
Nurture |
| At Risk |
Old |
Often |
High |
Win back |
| Hibernating |
Old |
Rare |
Low |
Re-engage or remove |
Lifecycle Segments
| Stage |
Definition |
Primary Workflow |
| Subscriber |
Email only |
Welcome, nurture |
| Lead |
Engaged, not converted |
Nurture, sales |
| Trial |
Active trial |
Onboarding |
| Customer |
Paying |
Onboarding, upsell |
| Churned |
Cancelled |
Win-back |
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
| Email Type |
Best Days |
Best Times |
| B2B |
Tue-Thu |
9-11am, 1-3pm |
| B2C |
Tue-Thu, Sat |
10am, 8pm |
| Transactional |
Immediate |
N/A |
| Newsletter |
Consistent day |
Your data |
Core: Deliverability Checklist
Authentication (Required)
List Hygiene
Sending Practices
Monitoring
| Metric |
Target |
Action if Below |
| Open rate |
>20% |
Check subject lines, sender reputation |
| Click rate |
>2% |
Check content, CTA, relevance |
| Bounce rate |
<2% |
Clean list, verify addresses |
| Spam rate |
<0.1% |
Review content, frequency, consent |
| Unsubscribe |
<0.5% |
Check frequency, relevance |
Platform Setup Guides
HubSpot
See resources/hubspot-setup.md
Klaviyo
See resources/klaviyo-setup.md
Mailchimp
See resources/mailchimp-setup.md
Quick Reference
| Task |
Template |
Location |
| Workflow design |
Workflow blueprint |
templates/workflow-blueprint.md |
| Welcome sequence |
Welcome flow |
templates/welcome-sequence.md |
| Nurture sequence |
Nurture flow |
templates/nurture-sequence.md |
| Cart abandonment |
Cart recovery |
templates/cart-abandonment.md |
| Email audit |
Health check |
templates/email-audit.md |
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
| Metric |
Definition |
Target |
| Open rate |
Opens / Delivered |
>20% |
| Click rate |
Clicks / Delivered |
>2% |
| Conversion rate |
Conversions / Clicks |
Varies |
| Revenue per email |
Revenue / Emails sent |
Track trend |
Workflow Metrics
| Metric |
Definition |
Purpose |
| Flow conversion |
Goal completions / Flow entries |
Workflow effectiveness |
| Drop-off rate |
Exits at each step |
Find weak points |
| Time to convert |
Days from entry to goal |
Optimize timing |
| Re-entry rate |
Multiple entries |
Check exclusions |
Templates
Anti-Patterns
| Anti-Pattern |
Why It Fails |
Instead |
| Batch-and-blast |
Low relevance, high unsubscribes |
Segment and trigger |
| No segmentation |
One size fits none |
Behavioral segments |
| Too many CTAs |
Decision paralysis |
One CTA per email |
| Ignoring mobile |
60%+ read on mobile |
Mobile-first design |
| No testing |
Assumptions vs data |
A/B test everything |
| Buying lists |
Spam complaints, reputation damage |
Build organically |
| No sunset policy |
Sending to dead addresses |
Remove unengaged |
Optional: AI / Automation
Note: Core email automation fundamentals above work without AI. This section covers optional AI capabilities.
AI Personalization
| Feature |
Use Case |
Tools |
| Subject line generation |
A/B test variants |
Claude, GPT, platform built-in |
| Dynamic content |
Personalized blocks |
Klaviyo, HubSpot, Braze |
| Send time optimization |
Per-recipient timing |
Seventh Sense, platform AI |
| Predictive segments |
Churn risk, purchase propensity |
Klaviyo, HubSpot predictive |
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
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"
