Advances in AI are widely understood to have implications for cybersecurity. Articles have emphasized the effect of AI on the cyber offense-defense balance, and commentators can be found arguing either that cyber will privilege attackers or defenders. For defenders, arguments are often made that AI will enable solutions like formal verification of all software--and for some well-equipped companies, this may be true. This conversation, however, does not match the reality for most companies. "Trailing-edge organizations," as we term them, rely heavily on legacy software, poorly staff security roles, and struggle to implement best practices like rapid deployment of security patches. These decisions may be the result of corporate inertia, but may also be the result of a seemingly-rational calculation that attackers may not bother targeting a firm due to lack of economic incentives, and as a result, underinvestment in defense will not be punished. This approach to security may have been sufficient prior to the development of AI systems, but it is unlikely to remain viable in the near future. We argue that continuing improvements in AI's capabilities poses additional risks on two fronts: First, increased usage of AI will alter the economics of the marginal cyberattack and expose these trailing-edge organizations to more attackers, more frequently. Second, AI's advances will enable attackers to develop exploits and launch attacks earlier than they can today--meaning that it is insufficient for these companies to attain parity with today's leading defenders, but must instead aim for faster remediation timelines and more resilient software. The situation today portends a dramatically increased number of attacks in the near future. Moving forward, we offer a range of solutions for both organizations and governments to improve the defensive posture of firms which lag behind their peers today.