In recent years, the Web has become an ever more sophisticated and irreplaceable tool in our daily lives. While the visual Web has been advancing at a rapid pace, assistive technology has not been able to keep up, increasingly putting visually impaired users at a disadvantage. Web automation has the potential to bridge the accessibility divide between the ways blind and sighted people access the Web; specifically, it can enable blind people to accomplish quickly web browsing tasks that were previously slow, hard, or even impossible to complete. In this paper, we propose guidelines for the design of intuitive and accessible web automation that has the potential to increase accessibility and usability of web pages, reduce interaction time, and improve user browsing experience. Our findings and a preliminary user study demonstrate the feasibility of and emphasize the pressing need for truly accessible web automation technologies.