Information Technology (IT) service contracts imply a transfer of risk between parties. There has been little research conducted on how firms can apply quantitative analysis of risk factors in IT service delivery and contract negotiation. This dissertation applies risk management theory and methods from financial economics to inform negotiation of contractual parameters in IT Services agreements. The research offers contributions to the development and application of risk management and investment under uncertainty models to the problem space of information technology services investment. I develop a new model for managing risk in IT services contracts. In addition, I develop new analytic models to provide both valuation and strategic direction for benchmarking IT services under opaque conditions of market opaqueness and price volatility. Essay 1 develops the optimal trade-offs of risk and return in contract negotiation and introduces a new method IT Services Profit-at-Risk for evaluating contractual concessions. Essay 2 provides a model of valuing price benchmark provisions in IT services contracts and gives guidance on how to value and when to execute these provisions. Essay 3 examines the role of visibility of the market prices of IT services and provides a model for valuing market price information in the context of IT services price benchmarks.