Crossing the Chasm to Enterprise: Why Your SMB Roadmap Will Fail Big Clients
January 7, 2026 • 10 min read
SMB roadmaps fail upmarket because the buyer changes. In a small company the user and the buyer are the same person; in an enterprise the buyer is IT, security and procurement, and they judge you on provisioning, audit logs, compliance and uptime rather than on the features your users love. You just lost a $100k […]