AI That Works: Calendly’s 10 Lessons

Calendly's journey into AI offers valuable insights for sales professionals aiming to integrate AI effectively into their workflows. Here are the key takeaways:

  • Address Real Problems: AI should enhance productivity by solving specific, high-friction issues users face daily.(SaaStr)

  • Avoid Parallel AI Products: Creating separate AI experiences can lead to low adoption. Instead, integrate AI seamlessly into existing workflows.(SaaStr)

  • Evaluate AI Investments Carefully: Assess AI initiatives based on customer value, cost structure, data quality, and user experience impact.(SaaStr)

  • Personalization at Scale: Use AI to personalize user experiences across all touchpoints, enhancing engagement and retention.(SaaStr)

  • Measure Meaningful Metrics: Focus on metrics like user engagement with AI features, task completion rates, and impact on core product metrics.(SaaStr)

  • Ensure Robust Data Architecture: A unified data infrastructure is crucial for consistent and effective AI experiences.(SaaStr)

  • Maintain Consistency Across Channels: AI should provide a consistent voice and experience across support, marketing, and product interfaces.(SaaStr)

  • Manage AI Costs Strategically: Be mindful of the costs associated with AI, especially at scale, and consider hybrid approaches for cost-intensive features.(SaaStr)

  • Implement 'Invisible AI': AI should operate seamlessly in the background, enhancing user experience without being obtrusive.

  • Prioritize Continuous Education: Offer AI-powered, contextual learning experiences to keep users engaged and loyal.

These lessons underscore the importance of integrating AI thoughtfully to enhance user experience and drive business growth.

Reference: Lemkin, J. (2025, April 17). Building AI That Actually Works: 10 Key Lessons from Calendly’s CPO and Head of UX. SaaStr.