This checklist serves as a guide for individuals responsible for hiring a Chief Information Security Officer (CISO). It outlines considerations for selecting a virtual Chief Information Security Officer (vCISO) or Deputy CISO, emphasizing the benefits of utilizing a DeepSeas CISO Advisory Program. The document details challenges faced in recruiting top talent for the CISO role, including high demand and limited supply, and highlights the advantages of a vCISO in terms of cost-effectiveness and access to a broader team of cybersecurity experts. It explains how a DeepSeas CISO can assist organizations in transforming their cybersecurity programs by evaluating existing measures and planning strategic improvements. The checklist also addresses options for those who already have a cyber leader but wish to enhance their cybersecurity efforts through additional advisory services. Overall, the document provides a structured approach to evaluating the CISO role and the potential benefits of engaging with DeepSeas for cybersecurity leadership.