Zendesk successfully transitioned from serving small businesses to catering to enterprises while maintaining its focus on simplicity and accessibility. The company developed features that appealed to all customer segments, including single sign-on (SSO), compliance and security measures, premium support, and customization options. By following a "land and expand" sales model and focusing on both SMBs and enterprise customers, Zendesk grew from $1 million in revenue in 2008 to $1 billion in 2020.