The Chrome extension was once Clockwise’s core product, but had become cluttered, fragile, and nearly invisible to users. I led a 3.5-month redesign to restore trust and make the value of Clockwise more visible… especially around our key automation feature, Flexible Meetings.

After validating that rebuilding the old UI wasn’t sustainable, I proposed a new pattern: a lightweight, branded assistive panel (“the Sidecar”) that sat alongside Google Calendar, not inside it. This shift clarified automation, surfaced key settings when users needed them, and built trust through subtle, passive communication.

The launch led to increased engagement, higher flexible meeting adoption, and stronger user understanding of how Clockwise works. All without adding unnecessary complexity!