Droplr

Droplr is the screenshot capture and file sharing tool bootstrapped from the US by Scott Nagy and Cody Caldwell in 2010. It installs as a Mac and Windows app that intercepts screenshot shortcuts — instead of saving to the desktop, screenshots are automatically uploaded to the cloud and the URL is copied to clipboard in under 2 seconds. The platform grew to $2M+ ARR with a small team by being the default tool recommendation for designers and developers who share work-in-progress screenshots dozens of times per day. Droplr added basic annotation tools (arrows, text, blur for hiding sensitive information, crop) without the overhead of a full screen capture suite — the philosophy is that the most important tool is the fastest path from "I need to share this" to "URL is in my clipboard." Enterprise features (team boards where all screenshots are visible to teammates, access controls, custom domains like share.yourcompany.com) enabled per-seat billing to larger organizations. The enterprise pivot from individual developer tool to team sharing platform was the key revenue expansion move.