When is EV/Gross Profit a better multiple than EV/Revenue for tech companies?

When the comp set mixes business models with very different gross margins - e.g., an 85%-margin subscription software company against a 60%-margin usage/infrastructure business or a 30%-take-rate marketplace against a gross-recognized e-commerce player. EV/Revenue implicitly assumes every revenue dollar has equal earnings potential; EV/Gross Profit corrects for the first and biggest driver of that difference, since gross profit is what actually funds opex and eventually margin. It is especially useful for fintech, marketplaces, and consumption businesses where revenue recognition conventions (gross versus net) make revenue itself non-comparable. Limitation: it still ignores opex efficiency and growth durability, so it complements rather than replaces the full analysis.