Abstract: Detection and remediation of technical debt in software-intensive systems has received considerable attention in the software engineering literature. Yet, the strategic implications of technical debt are not well understood and the examination of technical debt through the decision calculus of a managerial audience is under explored. Drawing from my research and consulting projects, I outline a research agenda that calls attention to issues related to (1) design moves that act upon both technical debt and options embedded in enterprise systems, (2) the role played by design capital (i.e., the stock of debt and options in a system) in influencing adoption and maintenance of long-lived enterprise systems, (3) the influence of technical debt on corporate decisions, such as information technology (IT) outsourcing, and (4) the coevolution of debt embedded in technical systems and the business processes that they support. The research agenda aims to build bridges between the software engineering and technology management research communities, as well as to enrich and extend our efforts to theorize and analyze the complex dynamics of technical debt in enterprise IT ecosystems.