Jake Sullivan has a 30-60-90 day plan as a new senior Java developer. In the first 30 days, he will focus on learning the company's tech stack and demonstrating Java coding skills. From days 30-60, his goals are to work on a new sync feature and get AWS certification. By days 60-90, Jake aims to finish coding the sync feature, propose improvements, and help build requirements for future features. He will be evaluated based on manager feedback, certification scores, issue reports, and meeting deadlines.