Box

Box is a strong pick for small businesses in regulated industries — like healthcare, legal, or financial services — that need serious document security and built-in e-signatures.

The biggest pro is that you get enterprise-grade security and compliance tools at a price most small teams can manage, starting at $15 per user per month. The main downside is that the best AI features and compliance tools are locked behind pricier plans, so smaller teams on the entry-level Business plan may feel limited.