Product Milestones
Users hit value, not approvals
Activation looks healthy. Users deepen usage. But free-to-paid conversion stalls because approval sits elsewhere.
Signal: Strong engagement, weak conversion
Buyer Friction
Security and procurement questions arrive early
High-intent accounts ask about SSO, legal, admin, or procurement before the motion is designed for it.
Signal: Buyer friction before purchase step
Expansion
Expansion only happens after human intervention
Product generates intent, but a human layer is needed to translate that intent into revenue.
Signal: Sales-assisted upgrade rate is high