This dissertation consists of two essays on the role of incomplete information, and the timing with which it is revealed, in agents' strategic behavior and the mechanisms that are designed to account for this behavior. The first essay studies the question of optimal information provision by a monopolist platform when sellers learn about key features of the auction process as they gain experience. Online platforms often do not directly control users' pricing strategy, and instead offer analytics and other information to help steer user behavior. I study how information provision by an auction platform to sellers shapes platform fees and outcomes using data from eBay auctions of children's toys. I present evidence that new sellers face uncertainty about how to set optimal reserve prices: they set lower reserve prices and earn higher revenues as they gain more experience. I develop a model where new sellers learn to set reserve prices on an auction platform with selective participation, and I show that sellers choose reserve prices to both extract surplus from bidders and attract additional bidders to their auction. I provide conditions under which new sellers' beliefs about the effect of reserve prices on bidder arrival are semiparametrically identified. Estimates from the learning model indicate that new sellers underestimate the effect of high reserve prices on deterring bidder entry, which leads to higher reserve prices and more items listed than for fully-informed sellers. Counterfactual simulations show that platform information provision can help new sellers learn the true bidder arrival process, which increases bidder entry as well as seller and platform profits. However, when jointly choosing information provision and platform fees, it may be optimal to not fully reveal information to sellers.

The second essay studies the timing of contract design in large corporate transactions, where the suitability of various contract terms for a particular deal is not known until firms expend costly effort developing these terms. Significant corporate transactions (such as financing and acquisition agreements) are typically negotiated in stages, wherein core pricing terms are fixed early while most non-price provisions are relegated to subsequent bargaining. This ordering stands in stark (and curious) contrast with canonical theories of contract design, which overwhelmingly counsel that non-price terms should be set first, saving price negotiations for last so as to fine tune the parties' net payoffs. This longstanding disjunction between theory and practice has become a celebrated puzzle for transactional design. We present an analytic framework that helps to reconcile the two, marrying a bargaining model and a search game over innovative contractual provisions. Our framework delivers a robust and tractable set of intuitions about when fixing price before other terms optimally incentivizes strategic search investments by the contracting parties. Our analysis is also amenable to making counterfactual comparisons of regimes where price is (and is not) set first, generating in the process several empirically testable implications.