This book contains 14 cases with challenges confronting Chief Information Officers in the largest and most interesting Danish companies, including the three most iconic ones: LEGO (biggest global toy manufacturer), Maersk (biggest global container shipping company) and NOVO (biggest global insulin company). It includes interesting cases from banks, energy, manufacturing, media, retail, gambling, hospitals, and government. The topics cover a range of key issues such as IT for disruption, coping with technological debt, IT challenges in acquisitions, outsourcing, IT security, creating open IT platforms, open innovations, and several other fascinating issues. The cases are especially relevant as teaching cases. All cases end with a list of possible key questions, a five minute video available for class or home study and a one hour video for in depth analysis of the case. Teaching notes are available for faculty.