From 48f9f9ce79d375ef7611337c91c20dfd4fa74dc3 Mon Sep 17 00:00:00 2001
From: Corey Haines <34802794+coreyhaines31@users.noreply.github.com>
Date: Thu, 15 Jan 2026 16:14:20 -0800
Subject: [PATCH] Expand email-sequence with comprehensive email types
 reference

Added detailed guidance for 20+ email types organized by category:

Onboarding:
- New users series, new customers series
- Key onboarding step reminders, new user invites

Retention:
- Upgrade to paid/higher plan, ask for review
- Proactive support, usage reports, NPS, referral program

Billing:
- Switch to annual, failed payment recovery
- Cancellation survey, renewal reminders

Usage:
- Daily/weekly/monthly summaries
- Key event and milestone notifications

Win-Back:
- Expired trials, cancelled customers

Campaigns:
- Monthly roundup, seasonal promotions
- Product updates, industry news, pricing updates

Also added email audit checklist for program review.

Co-Authored-By: Claude Opus 4.5 <noreply@anthropic.com>
---
 skills/email-sequence.md | 509 +++++++++++++++++++++++++++++++++++++++
 1 file changed, 509 insertions(+)

diff --git a/skills/email-sequence.md b/skills/email-sequence.md
index 9f078fa..42ac0bc 100644
--- a/skills/email-sequence.md
+++ b/skills/email-sequence.md
@@ -267,6 +267,515 @@ Coordinate with in-app onboarding. Email supports, doesn't duplicate.
 
 ---
 
+## Email Types Reference
+
+A comprehensive guide to lifecycle and campaign emails. Use this as an audit checklist and implementation reference.
+
+### Onboarding Emails
+
+#### New Users Series
+**Trigger**: User signs up (free or trial)
+**Goal**: Activate user, drive to aha moment
+**Typical sequence**: 5-7 emails over 14 days
+
+- Email 1: Welcome + single next step (immediate)
+- Email 2: Quick win / getting started (day 1)
+- Email 3: Key feature highlight (day 3)
+- Email 4: Success story / social proof (day 5)
+- Email 5: Check-in + offer help (day 7)
+- Email 6: Advanced tip (day 10)
+- Email 7: Upgrade prompt or next milestone (day 14)
+
+**Key metrics**: Activation rate, feature adoption
+
+---
+
+#### New Customers Series
+**Trigger**: User converts to paid
+**Goal**: Reinforce purchase decision, drive adoption, reduce early churn
+**Typical sequence**: 3-5 emails over 14 days
+
+- Email 1: Thank you + what's next (immediate)
+- Email 2: Getting full value — setup checklist (day 2)
+- Email 3: Pro tips for paid features (day 5)
+- Email 4: Success story from similar customer (day 7)
+- Email 5: Check-in + introduce support resources (day 14)
+
+**Key point**: Different from new user series—they've committed. Focus on reinforcement and expansion, not conversion.
+
+---
+
+#### Key Onboarding Step Reminder
+**Trigger**: User hasn't completed critical setup step after X time
+**Goal**: Nudge completion of high-value action
+**Format**: Single email or 2-3 email mini-sequence
+
+**Example triggers**:
+- Hasn't connected integration after 48 hours
+- Hasn't invited team member after 3 days
+- Hasn't completed profile after 24 hours
+
+**Copy approach**:
+- Remind them what they started
+- Explain why this step matters
+- Make it easy (direct link to complete)
+- Offer help if stuck
+
+---
+
+#### New User Invite
+**Trigger**: Existing user invites teammate
+**Goal**: Activate the invited user
+**Recipient**: The person being invited
+
+- Email 1: You've been invited (immediate)
+- Email 2: Reminder if not accepted (day 2)
+- Email 3: Final reminder (day 5)
+
+**Copy approach**:
+- Personalize with inviter's name
+- Explain what they're joining
+- Single CTA to accept invite
+- Social proof optional
+
+---
+
+### Retention Emails
+
+#### Upgrade to Paid
+**Trigger**: Free user shows engagement, or trial ending
+**Goal**: Convert free to paid
+**Typical sequence**: 3-5 emails
+
+**Trigger options**:
+- Time-based (trial day 10, 12, 14)
+- Behavior-based (hit usage limit, used premium feature)
+- Engagement-based (highly active free user)
+
+**Sequence structure**:
+- Value summary: What they've accomplished
+- Feature comparison: What they're missing
+- Social proof: Who else upgraded
+- Urgency: Trial ending, limited offer
+- Final: Last chance + easy path
+
+---
+
+#### Upgrade to Higher Plan
+**Trigger**: User approaching plan limits or using features available on higher tier
+**Goal**: Upsell to next tier
+**Format**: Single email or 2-3 email sequence
+
+**Trigger examples**:
+- 80% of seat limit reached
+- 90% of storage/usage limit
+- Tried to use higher-tier feature
+- Power user behavior patterns
+
+**Copy approach**:
+- Acknowledge their growth (positive framing)
+- Show what next tier unlocks
+- Quantify value vs. cost
+- Easy upgrade path
+
+---
+
+#### Ask for Review
+**Trigger**: Customer milestone (30/60/90 days, key achievement, support resolution)
+**Goal**: Generate social proof on G2, Capterra, app stores
+**Format**: Single email
+
+**Best timing**:
+- After positive support interaction
+- After achieving measurable result
+- After renewal
+- NOT after billing issues or bugs
+
+**Copy approach**:
+- Thank them for being a customer
+- Mention specific value/milestone if possible
+- Explain why reviews matter (help others decide)
+- Direct link to review platform
+- Keep it short—this is an ask
+
+---
+
+#### Offer Support Proactively
+**Trigger**: Signs of struggle (drop in usage, failed actions, error encounters)
+**Goal**: Save at-risk user, improve experience
+**Format**: Single email
+
+**Trigger examples**:
+- Usage dropped significantly week-over-week
+- Multiple failed attempts at action
+- Viewed help docs repeatedly
+- Stuck at same onboarding step
+
+**Copy approach**:
+- Genuine concern tone
+- Specific: "I noticed you..." (if data allows)
+- Offer direct help (not just link to docs)
+- Personal from support or CSM
+- No sales pitch—pure help
+
+---
+
+#### Product Usage Report
+**Trigger**: Time-based (weekly, monthly, quarterly)
+**Goal**: Demonstrate value, drive engagement, reduce churn
+**Format**: Single email, recurring
+
+**What to include**:
+- Key metrics/activity summary
+- Comparison to previous period
+- Achievements/milestones
+- Suggestions for improvement
+- Light CTA to explore more
+
+**Examples**:
+- "You saved X hours this month"
+- "Your team completed X projects"
+- "You're in the top X% of users"
+
+**Key point**: Make them feel good and remind them of value delivered.
+
+---
+
+#### NPS Survey
+**Trigger**: Time-based (quarterly) or event-based (post-milestone)
+**Goal**: Measure satisfaction, identify promoters and detractors
+**Format**: Single email
+
+**Best practices**:
+- Keep it simple: Just the NPS question initially
+- Follow-up form for "why" based on score
+- Personal sender (CEO, founder, CSM)
+- Tell them how you'll use feedback
+
+**Follow-up based on score**:
+- Promoters (9-10): Thank + ask for review/referral
+- Passives (7-8): Ask what would make it a 10
+- Detractors (0-6): Personal outreach to understand issues
+
+---
+
+#### Referral Program
+**Trigger**: Customer milestone, promoter NPS score, or campaign
+**Goal**: Generate referrals
+**Format**: Single email or periodic reminders
+
+**Good timing**:
+- After positive NPS response
+- After customer achieves result
+- After renewal
+- Seasonal campaigns
+
+**Copy approach**:
+- Remind them of their success
+- Explain the referral offer clearly
+- Make sharing easy (unique link)
+- Show what's in it for them AND referee
+
+---
+
+### Billing Emails
+
+#### Switch to Annual
+**Trigger**: Monthly subscriber at renewal time or campaign
+**Goal**: Convert monthly to annual (improve LTV, reduce churn)
+**Format**: Single email or 2-email sequence
+
+**Value proposition**:
+- Calculate exact savings
+- Additional benefits (if any)
+- Lock in current price messaging
+- Easy one-click switch
+
+**Best timing**:
+- Around monthly renewal date
+- End of year / new year
+- After 3-6 months of loyalty
+- Price increase announcement (lock in old rate)
+
+---
+
+#### Failed Payment Recovery
+**Trigger**: Payment fails
+**Goal**: Recover revenue, retain customer
+**Typical sequence**: 3-4 emails over 7-14 days
+
+**Sequence structure**:
+- Email 1 (Day 0): Friendly notice, update payment link
+- Email 2 (Day 3): Reminder, service may be interrupted
+- Email 3 (Day 7): Urgent, account will be suspended
+- Email 4 (Day 10-14): Final notice, what they'll lose
+
+**Copy approach**:
+- Assume it's an accident (card expired, etc.)
+- Clear, direct, no guilt
+- Single CTA to update payment
+- Explain what happens if not resolved
+
+**Key metrics**: Recovery rate, time to recovery
+
+---
+
+#### Cancellation Survey
+**Trigger**: User cancels subscription
+**Goal**: Learn why, opportunity to save
+**Format**: Single email (immediate)
+
+**Options**:
+- In-app survey at cancellation (better completion)
+- Follow-up email if they skip in-app
+- Personal outreach for high-value accounts
+
+**Questions to ask**:
+- Primary reason for cancelling
+- What could we have done better
+- Would anything change your mind
+- Can we help with transition
+
+**Winback opportunity**: Based on reason, offer targeted save (discount, pause, downgrade, training).
+
+---
+
+#### Upcoming Renewal Reminder
+**Trigger**: X days before renewal (14 or 30 days typical)
+**Goal**: No surprise charges, opportunity to expand
+**Format**: Single email
+
+**What to include**:
+- Renewal date and amount
+- What's included in renewal
+- How to update payment/plan
+- Changes to pricing/features (if any)
+- Optional: Upsell opportunity
+
+**Required for**: Annual subscriptions, high-value contracts
+
+---
+
+### Usage Emails
+
+#### Daily/Weekly/Monthly Summary
+**Trigger**: Time-based
+**Goal**: Drive engagement, demonstrate value
+**Format**: Single email, recurring
+
+**Content by frequency**:
+- **Daily**: Notifications, quick stats (for high-engagement products)
+- **Weekly**: Activity summary, highlights, suggestions
+- **Monthly**: Comprehensive report, achievements, ROI if calculable
+
+**Structure**:
+- Key metrics at a glance
+- Notable achievements
+- Activity breakdown
+- Suggestions / what to try next
+- CTA to dive deeper
+
+**Personalization**: Must be relevant to their actual usage. Empty reports are worse than no report.
+
+---
+
+#### Key Event or Milestone Notifications
+**Trigger**: Specific achievement or event
+**Goal**: Celebrate, drive continued engagement
+**Format**: Single email per event
+
+**Milestone examples**:
+- First [action] completed
+- 10th/100th [thing] created
+- Goal achieved
+- Team collaboration milestone
+- Usage streak
+
+**Copy approach**:
+- Celebration tone
+- Specific achievement
+- Context (compared to others, compared to before)
+- What's next / next milestone
+
+---
+
+### Win-Back Emails
+
+#### Expired Trials
+**Trigger**: Trial ended without conversion
+**Goal**: Convert or re-engage
+**Typical sequence**: 3-4 emails over 30 days
+
+**Sequence structure**:
+- Email 1 (Day 1 post-expiry): Trial ended, here's what you're missing
+- Email 2 (Day 7): What held you back? (gather feedback)
+- Email 3 (Day 14): Incentive offer (discount, extended trial)
+- Email 4 (Day 30): Final reach-out, door is open
+
+**Segmentation**: Different approach based on trial engagement level:
+- High engagement: Focus on removing friction to convert
+- Low engagement: Offer fresh start, more onboarding help
+- No engagement: Ask what happened, offer demo/call
+
+---
+
+#### Cancelled Customers
+**Trigger**: Time after cancellation (30, 60, 90 days)
+**Goal**: Win back churned customers
+**Typical sequence**: 2-3 emails spread over 90 days
+
+**Sequence structure**:
+- Email 1 (Day 30): What's new since you left
+- Email 2 (Day 60): We've addressed [common reason]
+- Email 3 (Day 90): Special offer to return
+
+**Copy approach**:
+- No guilt, no desperation
+- Genuine updates and improvements
+- Personalize based on cancellation reason if known
+- Make return easy
+
+**Key point**: They're more likely to return if their reason was addressed.
+
+---
+
+### Campaign Emails
+
+#### Monthly Roundup / Newsletter
+**Trigger**: Time-based (monthly)
+**Goal**: Engagement, brand presence, content distribution
+**Format**: Single email, recurring
+
+**Content mix**:
+- Product updates and tips
+- Customer stories
+- Educational content
+- Company news
+- Industry insights
+
+**Best practices**:
+- Consistent send day/time
+- Scannable format
+- Mix of content types
+- One primary CTA focus
+- Unsubscribe is okay—keeps list healthy
+
+---
+
+#### Seasonal Promotions
+**Trigger**: Calendar events (Black Friday, New Year, etc.)
+**Goal**: Drive conversions with timely offer
+**Format**: Campaign burst (2-4 emails)
+
+**Common opportunities**:
+- New Year (fresh start, annual planning)
+- End of fiscal year (budget spending)
+- Black Friday / Cyber Monday
+- Industry-specific seasons
+- Back to school / work
+
+**Sequence structure**:
+- Announcement: Offer reveal
+- Reminder: Midway through promotion
+- Last chance: Final hours
+
+---
+
+#### Product Updates
+**Trigger**: New feature release
+**Goal**: Adoption, engagement, demonstrate momentum
+**Format**: Single email per major release
+
+**What to include**:
+- What's new (clear and simple)
+- Why it matters (benefit, not just feature)
+- How to use it (direct link)
+- Who asked for it (community acknowledgment)
+
+**Segmentation**: Consider targeting based on relevance:
+- Users who would benefit most
+- Users who requested feature
+- Power users first (for beta feel)
+
+---
+
+#### Industry News Roundup
+**Trigger**: Time-based (weekly or monthly)
+**Goal**: Thought leadership, engagement, brand value
+**Format**: Curated newsletter
+
+**Content**:
+- Curated news and links
+- Your take / commentary
+- What it means for readers
+- How your product helps
+
+**Best for**: B2B products where customers care about industry trends.
+
+---
+
+#### Pricing Update
+**Trigger**: Price change announcement
+**Goal**: Transparent communication, minimize churn
+**Format**: Single email (or sequence for major changes)
+
+**Timeline**:
+- Announce 30-60 days before change
+- Reminder 14 days before
+- Final notice 7 days before
+
+**Copy approach**:
+- Clear, direct, transparent
+- Explain the why (value delivered, costs increased)
+- Grandfather if possible (lock in old rate)
+- Give options (annual lock-in, downgrade)
+
+**Important**: Honesty and advance notice build trust even when price increases.
+
+---
+
+## Email Audit Checklist
+
+Use this to audit your current email program:
+
+### Onboarding
+- [ ] New users series
+- [ ] New customers series
+- [ ] Key onboarding step reminders
+- [ ] New user invite sequence
+
+### Retention
+- [ ] Upgrade to paid sequence
+- [ ] Upgrade to higher plan triggers
+- [ ] Ask for review (timed properly)
+- [ ] Proactive support outreach
+- [ ] Product usage reports
+- [ ] NPS survey
+- [ ] Referral program emails
+
+### Billing
+- [ ] Switch to annual campaign
+- [ ] Failed payment recovery sequence
+- [ ] Cancellation survey
+- [ ] Upcoming renewal reminders
+
+### Usage
+- [ ] Daily/weekly/monthly summaries
+- [ ] Key event notifications
+- [ ] Milestone celebrations
+
+### Win-Back
+- [ ] Expired trial sequence
+- [ ] Cancelled customer sequence
+
+### Campaigns
+- [ ] Monthly roundup / newsletter
+- [ ] Seasonal promotion calendar
+- [ ] Product update announcements
+- [ ] Pricing update communications
+
+---
+
 ## Email Copy Guidelines
 
 ### Structure