Organizations are under increasing pressure to adopt Internet-based e-business solutions for improving internal efficiency and collaboration with partners, suppliers, and customer firms within the environment of e-business webs. To realize these benefits, companies must transition towards an e-business organization. Such transformation demands IT knowledge and expertise at different levels. Each level requires special IT skills introduced as a result of the complex and dynamic nature of an e-business environment. In this chapter we examine the e-business environment and its implications for firm-level IT skills portfolio management. We then present five levels of challenges related to an e-business firm’s IT skills requirement. We further present: (1) future trends relating to the changing landscape for e-business IT skills; (2) activities that support acquisition, development, and maintenance of these skills; and (3) the gap between academic programs and e-business needs. In conclusion, we propose a research agenda.