Calendly

Unlocking Customer Value & Reducing Churn

My Role

Staff Product Designer

Project Dates

Q1-Q4 2024

Head of Product
Senior Product Managers (2)
Senior Product Designers (3)
Senior Engineering Managers (3)
Software Engineers (various levels) (16)

Team

Context

Overview

I led multiple projects focused on simplifying Calendly’s scheduling workflows, specifically targeting individuals in teams of 1-20. The goal was to reduce churn and increase conversions to paid plans by addressing key user pain points.

Business Problem

78% of new revenue (~$87M/$112M) was offset in 2023 due to customer churn.

Users reported not finding enough value in the product to continue to pay for a subscription.

User Problem

Process

Understanding the Problem: Why are Customers Leaving?

By analyzing product usage data, reviewing support tickets, conducting user surveys, and performing moderated user interviews, I uncovered key insights into unmet user needs. 

Key Insight: Poor discoverability of specific advanced scheduling and sharing features

Solution

Improve the discoverability of key scheduling features (1) and enhance sharing features (2) to increase perceived value and reduce churn

Part 1: Product audit to assess issues with current scheduling features

Calendly offers five different "scheduling link" options, many of which have confusing names and hidden creation points, likely contributing to discoverability issues.

Architecture Updates: Simplifying scheduling links

To simplify scheduling options, I consolidated the 5 types of scheduling links to 3 and updated naming conventions based on user feedback. Doing so did not remove any current functionality.

UI Updates: Organizing scheduling features

To enhance discoverability, I added tabs for single-use links and meeting polls under the new “Scheduling” page. To clearly differentiate types of scheduling links, I consolidated scheduling link creation entry points to a single button, which opens a drop down menu detailing the benefits of each type of link.

User Testing

  • Users mentioned that they were interested in the “new” ways to schedule (meeting polls and single-use links)

  • Validated an increase in discoverability

  • Validated value of single-use links and meeting polls

  • Validated usability of accessing all three link types (15/16 users completed the task given)

Part 2: Evaluating problems with the current sharing experience

“Add times to email” and “customize & share” were features that were not discoverable, but rated as highly valuable by users

Design: Rethinking how users are expose to sharing options

I updated the visual and interaction design of the meeting type component to improve discoverability of “add times to email”, highlight a new option to send availability directly from Calendly, and ensure nomenclature alignment with user mental models.

Component updates: Meeting type cards

Cross-platform Implementation

I then worked with product and design partners responsible for the mobile app and extension to implement the scheduling and sharing updates across the mobile app and the web extension.

Final Solution: Full prototype

Results

Success metrics (Pending Q4, 2024 Launch)

Based on positive user feedback during usability testing, we anticipate a 10% increase in single-use link adoption and a 5% reduction in churn among target users within the first quarter post-launch.