The dynamics of innovation in complex products and systems (CoPS) is based on projects and differs from the mass production industries. Many of the investments related to CoPS require the development of cutting-edge technologies and their integration into large and complex systems, requiring appropriate methodologies for risk assessment and management for these investments. Projects are not only part of the operational side but are critical to business innovation, capacity development, and corporate strategy. Determining adequate success criteria and establishing a project categorization system are critical for assessing innovation projects. This article firstly shows the proposal and evaluation of the success criteria model for Oil and Gas projects. From this evaluation, a program was proposed to introduce technologies in systems, aiming at evolving systems and their convergence with the corporate strategy. A categorization system was then proposed to assess innovation projects in this program, based on the diamond approach. It was applied to case studies. The evaluation showed positive results and provided insights about the relative importance of success criteria dimensions. This study contributes to the theory with adaptations to existing models, a program proposal, and empirical data. Organizations dealing with CoPS, especially in the Oil and Gas sector, may benefit from the models and insights presented here.