The Breakout Growth Podcast

Cracking the Viral Loop: Calendly’s Playbook for Freemium Growth

12 snips
Apr 8, 2025
Darren Chait, VP of Marketing at Calendly, discusses the secrets behind the company's explosive growth through its unique freemium model and virality. He emphasizes the importance of customer feedback in refining features and driving retention. Chait explains how simplicity and cross-functional collaboration are crucial for success, while AI is utilized to enhance user engagement. Listeners will gain insights on navigating growth metrics and the delicate balance between innovation and retaining focus on what users truly need.
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ANECDOTE

Darren's Acquisition Journey

  • Darren Chait joined Calendly through an acquisition of his startup Hugo in 2022.
  • Hugo focused on meeting workflows and note-taking, fitting well with Calendly's mission.
INSIGHT

Viral Loop of Scheduling

  • Meeting scheduling naturally creates a viral loop since it involves multiple people.
  • Users quickly recognize Calendly's value when scheduling, driving organic growth.
ADVICE

Freemium Enables Viral Growth

  • Freemium is essential for Calendly's viral loop and long-term user nurture.
  • It allows users to convert when ready, beyond limited free trials.
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