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10 Key Lessons from Calendly’s CPO and Head of UX on Building AI that Actually Works

  • Calendly is focusing on implementing AI throughout its entire customer experience, aiming to transform interactions in apps and products.
  • Lessons learned include the failure of parallel AI interfaces, challenges in meeting core metrics, and the importance of not disrupting functional aspects with unnecessary AI.
  • Successful AI integration involves solving real problems, avoiding parallel AI products, evaluating ROI factors, and achieving personalization at scale.
  • Key metrics for AI success include user engagement, task completion rates, impact on core product metrics, and customer loyalty rates.
  • Data architecture, multi-channel AI experiences, cost management, and the 'Invisible AI' principle are highlighted as crucial for AI success.
  • Continuous education as a retention strategy, the importance of genuine product-market fit, and the need for customer feedback are emphasized for success in the AI era.
  • Challenges faced by Calendly include the failure of a conversational scheduling chatbot, generic AI recommendations, over-branding AI features, and cross-channel consistency issues.
  • Real success in AI requires a focus on customer needs, high-quality experiences, and a holistic approach to all customer interactions.

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