A company that cannot express what its product is worth in the customer's own numbers will discount under pressure, lose renewals it should win, and never raise prices. This is one of the most tractable problems in the first 100 days after an acquisition.
Seat-based pricing is no longer the default it was, and among the companies buyers look at in this range it often was not the default to begin with. What matters in diligence is not which model a target uses but whether anyone has examined it since it was set, and what moving it would cost.
ARR is a management convention, not an accounting standard, and the convention is set by the seller. Reconstructing the recurring base from billing data rather than accepting the ARR schedule is often the single largest price mover in a software deal.
Software margins are under pressure from infrastructure and inference costs, but the pressure is uneven and the industry median has not moved. That gap between the aggregate and the cohort is the thing to examine, because a healthy blended margin can hide accounts that lose money.
A customer logo in a deck asserts that the company bought, that they are still customers, and that the relationship is meaningful. The slide distinguishes none of the 3, and all of them are testable before you have any access at all.
A company that succeeds in one market often treats the second as a question of introductions rather than strategy. The competitive set is different, the buying process is different, and in Europe sovereignty requirements have moved from preference to written specification. This plays out over quarters, which is why it belongs at board level.
Flexibility and customization are not differentiators, because a competitor can claim them and nobody can disprove them. Stickiness is different: it is a claim about switching cost, and switching cost leaves evidence in public.
Where the commercial engine turns out to be one or two people and one of them is the founder, that is not a red flag by itself. What matters is whether it is repeatable without them, and current quota attainment data makes rebuilding it slower and more expensive than a plan built on headcount alone suggests.
