Nand 2 Tetris[1] is a good starting place. You should get a good view of how the different level interact. Coursera have two cources [2][3] that cover the same material as the book
I second this course. It's awesome. The next step from there is probably Coursera's VLSI course, starting with https://www.coursera.org/learn/vlsi-cad-logic. It's all about how real-world VLSI CADs work.