sboghossian Growth — Email Onboarding Sequence
Purpose
New-user activation is the highest-leverage growth lever for a legal AI platform. Most users who sign up and never use the product are not opposed to it — they just never got far enough to experience real value. The 7-touch email sequence bridges that gap: it moves users from "signed up" to "integrated into workflow" over 30 days through progressively deeper prompts, social proof, and feature discovery.
This sequence is P0 because early activation directly determines long-term retention. Users who complete their first successful task within 3 days have dramatically higher 30-day retention.
Sequence overview
| Day | Subject line variant | Primary goal | Content |
|---|---|---|---|
| 0 | "Welcome to Louis" | Confirm + first step | Sign-up confirmation, 1-click first prompt, pricing context |
| 1 | "Pick your first skill" | First task activation | Persona-detected starter prompts, 30-second demo |
| 3 | "Need a hand?" | Re-engage dormant | Offer 1:1 demo; surface value props for non-activators |
| 7 | "Louis can do [X] — try it now" | Feature discovery | Highlight one underused feature matched to persona |
| 14 | "Your week with Louis" | Upgrade nudge | Usage summary + savings estimate; Pro plan benefits |
| 21 | "How [similar user] saves 5 hours/week" | Social proof | Persona-matched case study; soft CTA |
| 30 | "30 days in" | Renewal / survey | Recap progress; upgrade if appropriate; feedback survey if not |
Email specifications
Day 0 — Welcome
Trigger: immediately on sign-up confirmation.
Goal: confirm the user is in the right place and give them one clear next action.
Content elements:
- Warm welcome, brief statement of what Louis is (one sentence).
- 1-click CTA: "Start your first task" → opens pre-filled prompt matched to signup questionnaire.
- Brief pricing transparency note ("You're on the free tier — here's what you have").
- Support contact (human-reachable).
Tone: warm but professional. Lawyer-register for lawyer segment; accessible for consumer.
Day 1 — First skill
Trigger: 24 hours after sign-up if user has not completed a task.
Goal: drive first task completion.
Content elements:
- "Here's what people like you start with" — list 3 persona-matched prompts.
- Embedded or linked short demo: "Watch Louis draft a UAE NDA in 30 seconds."
- Single CTA: "Try it now."
Persona variants:
- Lawyer: first prompts focus on drafting (NDA, employment clause) or reviewing a document.
- SME founder: first prompts focus on contract review, terms of service.
- In-house: first prompts focus on policy review, employment agreement.
- Consumer: first prompts focus on understanding a contract or lease.
Day 3 — Re-engagement
Trigger: day 3 post-signup if fewer than 2 tasks completed.
Goal: identify and overcome barriers to first use.
Content elements:
- Acknowledge that getting started is sometimes hard: "Not sure where to begin?"
- Offer: 1:1 product demo (calendar link).
- Surface the top friction point (if known from analytics; otherwise: offer a guided first task).
- CTA options: "Book a demo" or "Try a guided task."
Do not send if: user has completed 3+ tasks in the first 3 days — they are activated, don't interrupt with a "beginner" email.
Day 7 — Feature reveal
Trigger: day 7 post-signup.
Goal: expand the user's mental model of what Louis can do.
Content elements:
- Highlight one specific underused feature matched to the user's role and active skills.
- Examples: "Did you know Louis can summarize a full clause library in one pass?" or "Try the bilingual AR/EN drafting mode."
- Single CTA to the specific feature.
Personalization: use user.active_skills to identify which features they have NOT used, then pick the highest-value unused feature for their persona.
Day 14 — Upgrade nudge
Trigger: day 14 post-signup.
Goal: convert free-tier users who have demonstrated value.
Content elements:
- Personal usage summary: "In your first 2 weeks, you completed [N] tasks and saved an estimated [X] minutes."
- Pro plan benefits relevant to their usage pattern (if they've hit free-tier limits, highlight the limit upgrade; if they've used drafting heavily, highlight saved templates).
- Side-by-side comparison of free vs Pro.
- Clear CTA: "Upgrade to Pro" with price.
Do not send if: user has already upgraded.
Day 21 — Case study
Trigger: day 21 post-signup.
Goal: social proof for users who have not yet upgraded or are showing churn signals.
Content elements:
- Open with a practitioner story: "How a corporate associate in Dubai cut NDA turnaround from 2 hours to 20 minutes."
- Story follows the [[growth-case-study-asker]] format: role, use case, outcome, quote.
- Persona-match the story to the user (lawyer story for lawyer users, etc.).
- Soft CTA: "See if Louis fits your workflow too" → links to a specific skill.
Day 30 — Progress recap
Trigger: day 30 post-signup.
Goal: consolidate activation, drive upgrade or collect feedback.
Content elements:
- "Here's your first month with Louis" recap card (tasks completed, time saved estimate, most-used skills).
- If user is on free tier and has hit value: upgrade CTA with first-month discount.
- If user has low activity: short feedback survey ("What would make Louis more useful for you?").
- If user is already on Pro: appreciation note + invitation to community / advisory program.
Sequence rules
- Unsubscribe link: required in every email. Respect immediately; no re-engagement attempts for 90 days post-unsubscribe.
- Emotional matter delay: if user has a matter flagged as distress (divorce, insolvency, urgent litigation), delay all non-essential emails by 24 hours.
- Personalization per persona: the copy is different for
lawyervssme-foundervsconsumer. Do not send generic copy — persona detection should gate which sequence variant fires. - A/B test subject lines: run at minimum a 2-variant test on each email subject line. Winning variant is the one with higher open rate at 48h.
- No duplicate sends: ensure idempotency — email platform must check "sent" flag before triggering each touch.
- Respect timezone: send each email at ~9am local time for the user's detected timezone.
Tracking metrics
| Metric | Target | Note |
|---|---|---|
| Day 0 open rate | > 70% | High because it's a confirmation email |
| Day 1 open rate | > 45% | |
| Day 1 CTA click rate | > 20% | Activation metric |
| Day 3 re-engagement open rate | > 30% | |
| Day 14 upgrade click rate | > 5% | Revenue metric |
| Day 30 upgrade conversion | > 3% | |
| Unsubscribe rate per email | < 1% | Alert if > 2% |
Related skills
- [[growth-push-notif-templates]]
- [[growth-nps-prompt]]
- [[growth-win-back-inactive]]
- [[growth-case-study-asker]]
- [[growth-referral-prompt]]