Subscription pricing at consumer software firms has converged on a small menu of tiers: typically a free version, a mid-priced plan, and a premium plan bundling nearly every feature. Executives often defend this convergence by citing the paradox of choice: offering finely differentiated prices, the argument runs, would confuse customers and depress conversion rates more than it would capture additional willingness to pay. It is true that laboratory studies of consumer choice have repeatedly found that expanding an assortment beyond roughly seven options tends to reduce purchase rates among first-time buyers. Yet this concession describes only the moment of initial selection; it says nothing about a customer who has already committed to a vendor and is choosing whether to upgrade. For that established customer, more granular tiers do not multiply comparison costs in the same way, because the customer already understands the product and is evaluating a single question: does the next tier's added functionality clear my price threshold? Firms that segment their upgrade paths, splitting a single premium tier into a team tier and a data tier priced against distinct usage patterns, consistently report higher upgrade revenue than firms that hold one premium price for all upgraders, even though both groups start from the same simplified menu at signup. A pricing team that imports the choice-paradox finding wholesale, treating it as a blanket argument against granularity, will under-price its most engaged customers, the very segment whose willingness to pay is best known and least risky to test. The efficient design keeps acquisition simple while letting the upgrade path branch, matching menu complexity to what each stage of the relationship can actually support.