Onboarding Check-in Drafter

Installation
SKILL.md

Available Context & Tools

@_platform-references/org-variables.md @_platform-references/capabilities.md

Onboarding Check-in Drafter

Goal

Generate stage-appropriate onboarding check-in emails at 7, 14, and 30 days after deal close. Each stage has a different tone and purpose: Day 7 focuses on setup assistance and quick wins, Day 14 checks progress and provides adoption tips, and Day 30 reviews success and opens expansion conversations. The tone evolves from tactical to strategic as the customer matures.

Why Proactive Onboarding Check-ins Matter

Structured onboarding check-ins are the single strongest predictor of customer retention and expansion:

  • Customers who receive a proactive check-in at day 7 have 41% higher feature adoption rates at day 30 compared to those who receive no outreach (Gainsight Onboarding Benchmarks, 2024).
  • Day 14 check-ins reduce time-to-value by 23% by surfacing blockers before they compound (ChurnZero retention study).
  • 30-day check-ins uncover expansion opportunities in 38% of accounts when framed as success reviews vs. product pitches (SaaStr Customer Success Survey).
  • 67% of customers churn within the first 90 days if they don't achieve an early win (ProfitWell retention data) — proactive check-ins identify and create those wins.
  • Customers who engage with onboarding resources shared in check-in emails have 2.4x higher lifetime value (Intercom Product Engagement Study).
Related skills
Installs
First Seen