Email onboarding drip sequence with behavioral triggers
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Prompt
Design a [num_emails]-email onboarding drip sequence for [product_type]. The goal is to take a new user from sign-up to their [activation_metric].
For each email:
1. Trigger condition (time-based or behavior-based)
2. Subject line (+ 2 alternatives)
3. Full email body (under 150 words)
4. One clear CTA
5. What happens if the user already completed the action (skip logic)
Include a flow diagram showing the branching logic.Customise this prompt
Fill in 3 variables to personalise this prompt
Preview
Design a [num_emails]-email onboarding drip sequence for [product_type]. The goal is to take a new user from sign-up to their [activation_metric].
For each email:
1. Trigger condition (time-based or behavior-based)
2. Subject line (+ 2 alternatives)
3. Full email body (under 150 words)
4. One clear CTA
5. What happens if the user already completed the action (skip logic)
Include a flow diagram showing the branching logic.
Example output
# Onboarding Email Sequence: CloudBoard (Project Management SaaS)
**Activation metric:** User creates their first board with 5+ tasks
**Sequence:** 7 emails over 14 days with behavioral branching
---
## Flow Diagram
```
Sign up
│
├── [Immediately] Email 1: Welcome + quick win
│
├── [+1 day, if NO board created] Email 2: Create your first board
│ └── [If board created] → Skip to Email 4
│
├── [+3 days, if board has < 5 tasks] Email 3: Add your tasks
│ └── [If 5+ tasks] → Skip to Email 5
│
├── [+5 days, if activated] Email 4: Pro tips for power users
│ └── [If NOT activated] Email 4b: "Is something blocking you?"
│
├── [+7 days] Email 5: Invite your team
│ └── [If already invited team] → Skip
│
├── [+10 days] Email 6: Feature spotlight (integrations)
│
└── [+14 days] Email 7: Upgrade nudge / feedback ask
└── [If on paid plan] → Send "thank you" variant instead
```
---
## Email 1: Welcome + Quick Win
**Trigger:** Immediately after sign-up
**Subject:** Welcome to CloudBoard — let's set up in 60 seconds
**Alt A:** Your first project board is waiting
**Alt B:** You're in! Here's your one next step
**Body:**
Hey [first_name]! 👋
Welcome to CloudBoard. You just joined 12,000+ teams who ship faster by keeping everything in one place.
Your first step is simple: **create a board.**
It takes 60 seconds. Here's what to do:
1. Click "New Board" on your dashboard
2. Give it a name (your current project works great)
3. Add 3-5 tasks you're working on this week
That's it. Once you have tasks on a board, everything else (collaboration, tracking, automation) clicks into place.
[Create my first board →]
If you need inspiration, here are 3 templates our users love:
- Product Launch Tracker
- Sprint Board
- Client Project Pipeline
Talk soon,
[Name] from CloudBoard
**CTA:** "Create my first board" button
**Skip logic:** If user already created a board during sign-up, skip to Email 3.
---
## Email 2: Create Your First Board (Nudge)
**Trigger:** 24 hours after sign-up AND user has NOT created a board
**Subject:** Still thinking about it? Here's a shortcut
**Alt A:** Your empty dashboard is lonely
**Alt B:** 60 seconds. That's all it takes.
**Body:**
Hey [first_name],
I noticed you haven't created your first board yet. No worries — most people browse around first.
Here's the fastest way to start: **use a template.**
Click any of these and you'll have a fully structured board in 10 seconds:
→ [Product Roadmap template]
→ [Weekly Sprint template]
→ [Personal Tasks template]
You can customize everything later. The important thing is getting your first tasks out of your head and onto a board.
[Pick a template →]
Fun fact: Users who create their first board within 48 hours are 4x more likely to still be using CloudBoard a month later.
**CTA:** "Pick a template"
**Skip logic:** If board created before this sends → skip entirely
---
## Email 3: Add Your Tasks
**Trigger:** 3 days after sign-up AND board exists with < 5 tasks
**Subject:** Your board has [X] tasks — here's why 5 is the magic number
**Alt A:** Almost there — add [5 - X] more tasks to unlock the magic
**Alt B:** Your board is working. Let's make it work harder.
**Body:**
Hey [first_name],
Great start — you've got [X] tasks on your board!
Here's something we've learned from watching thousands of teams: **5 tasks is the tipping point.** Below 5, a board feels like a list. Above 5, it starts to feel like a system.
At 5+ tasks, you unlock:
- **Priority sorting** — drag tasks to reorder what matters most
- **Status tracking** — see your progress at a glance
- **The satisfying "done" column** — trust us, it feels great
Add [5 - X] more tasks and your board transforms from a list into a workflow.
[Add tasks to my board →]
**Hint:** Don't overthink it. Dump everything on your plate this week. You can organize later.
**CTA:** "Add tasks to my board"
**Skip logic:** If 5+ tasks already → skip to Email 5
---
## Email 4: Pro Tips (Activated Users)
**Trigger:** 5 days after sign-up AND user has 5+ tasks (activated)
**Subject:** 3 tricks that save our power users 2 hours/week
**Alt A:** You're officially a CloudBoard pro — level up
**Alt B:** The features 90% of new users miss
**Body:**
Hey [first_name],
You've got a working board with real tasks — you're ahead of 70% of new users. Here are three features that'll save you serious time:
**1. Keyboard shortcuts**
Press `?` anywhere to see them all. The big ones: `N` = new task, `D` = set due date, `Space` = toggle task detail.
**2. Quick filters**
Click the filter icon on your board → filter by assignee, due date, or priority. Saves you from scrolling through 50 tasks.
**3. Slash commands in comments**
Type `/assign @name` or `/due friday` right in a comment. Manage tasks without opening the detail panel.
[See all keyboard shortcuts →]
---
## Email 4b: "Is Something Blocking You?" (Non-Activated)
**Trigger:** 5 days after sign-up AND user has NOT reached 5 tasks
**Subject:** Honest question — is CloudBoard working for you?
**Alt A:** We noticed you haven't finished setting up
**Alt B:** Quick question, [first_name]
**Body:**
Hey [first_name],
I'll be real — we noticed you signed up but haven't fully set up your board yet. I wanted to check in.
Is anything blocking you? Common things I hear:
- **"I don't have time right now"** → Reply "later" and I'll check back in 2 weeks
- **"It's not what I expected"** → Reply with what you were hoping for — I read every response
- **"I'm confused about how to start"** → Here's a 2-minute setup video: [link]
- **"I'm comparing tools"** → Fair! Here's how we compare to [top competitor]: [link]
No pressure either way. Just want to make sure you're not stuck.
[Reply to this email — I'm a real person]
---
## Email 5: Invite Your Team
**Trigger:** 7 days after sign-up (all users)
**Subject:** CloudBoard is 10x better with your team
**Alt A:** The feature that turns "my tool" into "our tool"
**Body:**
Hey [first_name],
You've been using CloudBoard solo for a week. Here's what changes when you invite your team:
- **Real-time updates** — see when teammates move tasks or add comments
- **@mentions** — loop someone in without leaving CloudBoard
- **Workload view** — see who's overloaded and who has bandwidth
Invite 2-3 teammates and your board becomes a living dashboard instead of a personal to-do list.
[Invite teammates →]
P.S. Everyone you invite gets their own free account. No credit card needed.
**Skip logic:** If user already invited teammates → skip
---
## Email 6: Feature Spotlight
**Trigger:** 10 days after sign-up
**Subject:** Connect CloudBoard to the tools you already use
**Body:**
Hey [first_name],
Quick one: CloudBoard connects to the tools your team already uses.
**Popular integrations:**
- **Slack** → Get board updates in your channels
- **GitHub** → Link PRs to tasks automatically
- **Google Calendar** → See due dates on your calendar
- **Figma** → Embed design links in task descriptions
Setting up takes about 2 minutes per integration.
[Browse all 30+ integrations →]
---
## Email 7: Upgrade or Feedback
**Trigger:** 14 days after sign-up
**Variant A (free user):**
**Subject:** Your free trial ends in 7 days — here's what you'd lose
**Body:** Summary of what they've accomplished (X tasks completed, Y hours tracked) + what Pro unlocks (unlimited boards, integrations, AI Assist). Soft upgrade CTA.
**Variant B (already paying):**
**Subject:** Thanks for being a CloudBoard customer 💙
**Body:** Thank you + ask for a quick NPS survey (1-10 rating). Offer to feature them as a case study if they score 9-10.