Should You Chase Enterprise Now Or Later?
Going upmarket is a sequence, not a slogan.
Usage is strong among 20-person teams. Enterprise prospects are curious, but every late-stage call surfaces admin controls, audit requirements, and reference questions the team cannot yet answer well. Expand upmarket only when trust becomes repeatable Enterprise readiness is a combination of ICP clarity, whole product, and the right human motion. Do not promote a segment into your active motion until you can name the repeatable proof and operating support it requires. What should you inspect first? Suppose enterprise users love the product, but security and admin rollout always stall. What follows? A mid-market segment starts showing the same admin questions…
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