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Calendly

Calendly delivers highly polished, visually distinctive emails, especially throughout a long and engaging onboarding flow filled with videos, feature nudges, and personalized prompts based on user activity. Their lifecycle messaging blends upgrade reminders, team-invite nudges, product-adoption prompts, and a rich cadence of educational webinars, including an on-demand onboarding session for new paid users.

They also maintain strong ongoing engagement through regular product-update emails from their Head of Product Marketing, win-back messages for churned users, and occasional expansion offers such as annual-plan discounts.

  • · 55 emails
  • · About 1 year and 1 month
  • · avg ~7 days between sends