Mat Keep for Oso

SMBs won’t scale you: The hard truth about expanding upmarket to win enterprise customers

Every high-growth software company eventually hits the same crossroads: Small and medium businesses (SMBs) can get you started, but only enterprises can get you scale. In this article, Oso , a unified permissions layer for apps and AI, explains what it really takes to break through.

Breakout Companies Hit Their Stride Only After Navigating The Enterprise Shift

For technology vendors, moving from SMBs to enterprises is the most reliable accelerant of growth. It’s also one of the hardest. Larger customers extend deal cycles and demand higher product maturity. The payoff: bigger contracts, faster revenue expansion, and stronger valuations.

Take Amazon Web Services as an example. A

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