Redesigning Calendly’s core scheduling architecture and sharing workflows to make high-value features easier to discover, contributing to a 6% reduction in churn.
Role
Staff Product Designer - led research, IA, interaction design, and cross-platform rollout
Team
2 Product Managers · 2 Senior Product Designers · 16 Software Engineers
Overview
Simplifying Calendly’s core scheduling model became a retention priority
The business problem
In 2023, customer churn offset 78% of new revenue, making retention a company-level priority. Users reported not finding enough value in the product to justify continuing their subscription.
Company goal
Reduce churn and improve paid conversion by helping individuals and small teams get more value from Calendly’s core scheduling capabilities.
Research
High-value scheduling features already existed—but users couldn’t find them
I combined usage data, support tickets, surveys, and moderated interviews to separate true feature gaps from discoverability problems. Several of users’ most-requested capabilities already existed, but adoption remained extremely low.
2/5
Top feature requests already existed
Pointing to a discoverability gap
5%
Adoption of customizable links
Despite being a top-requested capability
3%
Adoption of meeting polls
Despite being a top-requested capability
63%
Unaware of ability to share specific time slots
Despite users rating capability as valuable
Takeaway: Calendly already offered much of the functionality users wanted, but fragmented architecture and hidden entry points made it difficult to discover.
Scheduling Architecture
Reduce five overlapping scheduling objects to three clear concepts
Scheduling functionality was spread across five link types with inconsistent names and multiple creation points, making it difficult for users to understand which option to use.
Organizing each option around a distinct scheduling intent
I consolidated the overlapping link types into Meeting types, Single-use links, and Meeting polls, giving each a clearer purpose and aligning the naming around distinct user intents.
One hub made every scheduling option visible in context
I brought all three link types into a single Scheduling hub, organized them into clear tabs, and replaced scattered creation points with one menu that explained when to use each option.
Validation
15 of 16 users found all three scheduling options
Usability testing validated the new architecture, while also revealing how hidden several existing features had been in the previous experience.
15/16
Found all three scheduling options
Successfully completed the task
7/16
Thought existing features were new
Revealing how hidden they had been
56%
Found a relevant use case
For Single-use links or Meeting polls
Sharing Workflows
Make high-value sharing actions easier to discover
Users primarily interacted with meeting type cards, while fewer than 3% opened the Share modal. That modal contained valuable capabilities such as “Add times to email” and “Customize & share,” making discoverability—not feature availability—the primary problem.
Meeting type cards became the primary entry point for sharing
I redesigned the card hierarchy and interaction states to expose high-value actions without adding persistent clutter. Users could now book a meeting, offer time slots, share availability, or create a Single-use link directly from the place they already managed each meeting type.
Interaction System
One card pattern had to support multiple states and platforms
Cross-Platform Rollout
The same scheduling model had to work across three surfaces
I partnered with the mobile and extension teams to adapt the new scheduling and sharing model across surfaces while preserving the underlying information architecture and using interaction patterns appropriate to each platform.
Final Experience
A single scheduling hub for creating, managing, and sharing links
Impact
Lower churn and faster access to advanced scheduling
6%
Reduction in user churn
One quarter after launch
50%
Reduction in interaction steps
From 6 to 3 clicks