The landscape of measurable venture key performance indicators (KPIs) in the venture capital (VC) industry is dispersed and opaque, which is why they have not yet played the supportive decision-making role they potentially could have played so far. The limited and asymmetric information between the entrepreneurs and the investors leads to inefficient capital allocations, frictions, and agency problems. We address this transparency issue with a design science research approach by developing two artifacts: one for investors and one for entrepreneurs. For investors, transparency is increased by a portfolio reporting solution, which provides a useful “how-to-guide” on formal venture reporting processes and structures, supporting future venture selections, portfolio monitoring, and value-adding activities. For relevant groups of entrepreneurs, transparency is increased by a benchmarking solution, which provides useful descriptive insights on measurable venture KPIs and their relationships to venture milestones along the life cycle, such as funding events. The post-development evaluations of the artifacts show that practitioners have a strong need for such transparency. We conclude that beyond structural challenges of the venturing environment, such as pace, dynamics, and the inherent uniqueness of ventures, also the fragmentation of the VC industry seems to pose a key challenge to the establishment of a direct linkage between venture performance and measurable venture KPIs.