• Personalization

Dynamic Personalized Experiences Transform
Users into Advocates for Calendly

Calendly partnered with Cro Metrics to tackle key friction points across the user journey, from login struggles to underused product features. By designing personalized experiences that guided users toward meaningful action, we helped drive stronger trial-to-paid conversions, boost retention, and unlock deeper engagement.

The amount of experience that Cro Metrics has is very impressive. We’re able to learn best practices, and have the benefit of ideas and strategies that we wouldn’t otherwise have access to if run internally.

– Senior Director of Digital Product, Calendly

Calendly’s Challenges

  • User Journey Friction: Users struggled with accessing their calendar links, creating events quickly, and logging into their accounts, causing frustration and leading to a suboptimal experience.
  • Low Trial-to-Paid Conversions: Calendly sought innovative ways to drive trial users toward paid subscriptions by enhancing product appeal and decreasing the risk of users churning.
  • Underutilized Product Features: With users not fully exploring product features, Calendly sought ways to drive adoption and demonstrate the product’s true value.
  • Underperforming User Engagement: Users not creating enough calendar events hindered the product’s ability to drive meaningful usage, leading to lower retention rates and lost revenue potential.

Our Strategy:

Conceptualize & Plan: We partnered with Calendly’s marketing and product teams to co-create a testing strategy grounded in real user behavior, focusing on the three key actions that define successful engagement.

Test & Analyze: Built and launched targeted experiments based on user insights—capturing activity data, validating hypotheses, and surfacing actionable wins and areas to refine.

Iterate & Validate: Used real-time behavior and test learnings to continuously evolve strategy, fine-tune content, and drive compounding optimizations across the user journey.

Results

By eliminating friction, aligning messaging, and personalizing the user experience, we helped Calendly turn passive visits into meaningful action. What started as a static, misaligned homepage evolved into a dynamic experience that meets users where they are—with faster access, smarter CTAs, and real-time guidance.

The result? A +2.6% lift in product visits, +3.5% more events created, and a +5% increase in key actions taken.

Even better? Users noticed—publicly praising Calendly for the thoughtful UX and seamless design that gave them exactly what they needed, right when they needed it.

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