The First 90 Days Retention Checklist & Email Swipe File
Milestone-based playbook for the critical onboarding period. Checklist + 6 ready-to-use onboarding emails.
Part 1: The 90-Day Checklist
Day 1 • Day 7 • Day 14 • Day 30 • Day 60 • Day 90 • From Tether
Send welcome email within minutes. Trigger guided first action. Launch 3–5 step product tour.
Complete 4–6 onboarding email sequence. In-app checklist 3 of 5 done? Nudge. Behavioral triggers set.
Identify incomplete onboarding. Send recovery email. Target 40–60% checklist completion.
Send usage review + ROI summary. Feature adoption check. Flag at-risk (no first value).
Introduce secondary features. Watch for >30% usage drop. Re-engagement if quiet.
Success check-in. Annual plan offer. Expansion opportunity for heavy users.
Tether helps solo founders automate retention. Learn more at tether.so
Part 2: 6-Email Onboarding Sequence
Copy, customize, and drop into Customer.io, ConvertKit, or your ESP.
Email: Welcome
Subject: You're in — here's your first step
Hi {{first_name}},
Welcome to [Product]. You're literally one step away from your first win.
Here's what to do next: [Your #1 action - e.g., "Complete your profile" or "Import your first project"]
It takes about 2 minutes. Do it now and you'll see why [X type of users] love [Product].
[CTA Button: Get Started]
Questions? Just reply to this email—I read everything.
[Your name]Replace [brackets] with your product name, metrics, and CTAs.
Email: Getting Started
Subject: 3 tips to get more from [Product] in Week 1
Hi {{first_name}},
You've been with us for a few days. Here are 3 things that'll make [Product] stick:
1. [Tip 1 - ties to core value]
2. [Tip 2 - common "aha" moment]
3. [Tip 3 - power user shortcut]
Most users who do these 3 things in the first week end up as long-term customers. Give them a try.
[CTA: Open [Product]]Replace [brackets] with your product name, metrics, and CTAs.
Email: Feature Spotlight
Subject: The [Feature] that [saves time / unlocks X]
Hi {{first_name}},
Quick one: have you tried [Key Feature] yet?
It's the thing that [specific outcome - e.g., "cuts setup time in half" or "lets you automate X"].
Here's a 60-second overview: [Link to short video or doc]
[CTA: Try [Feature] now]
— [Your name]Replace [brackets] with your product name, metrics, and CTAs.
Email: Social Proof
Subject: How [Company Name] [achieved result] with [Product]
Hi {{first_name}},
[Company/Founder name] was where you are a few months ago. Now they [specific result - e.g., "save 10 hours/week" or "reduced churn by 40%"].
Their secret: [1-2 sentence summary of what they did differently].
You can do the same. Start with [one actionable step].
[CTA: See the full story] or [Get the same result]]Replace [brackets] with your product name, metrics, and CTAs.
Email: Usage Review
Subject: Here's what you've accomplished in 30 days
Hi {{first_name}},
You've been with [Product] for a month. Here's a quick recap:
• [Metric 1 - e.g., Projects created: X]
• [Metric 2 - e.g., Time saved: X hours]
• [Metric 3 - e.g., Reports run: X]
That's real value. Keep it going—[next milestone or tip].
[CTA: Open [Product]]Replace [brackets] with your product name, metrics, and CTAs.
Email: Upgrade Nudge
Subject: Ready to unlock [Pro feature]?
Hi {{first_name}},
You've been crushing it with [Product]. Based on your usage, you might be ready for [Pro/Annual benefit].
[One sentence on what they get: e.g., "Go annual and save 20%—plus get [feature]."]
[CTA: Upgrade now] or [See plans]
No pressure—you're doing great either way. Just wanted you to know the option exists.
[Your name]Replace [brackets] with your product name, metrics, and CTAs.
From the blog: The First 90 Days — Retention Strategies That Actually Work