Web-based coaching shows significant promise for linking teachers to highly expert practitioners. This is particularly important in districts that cannot afford to hire full-time school-based coaches or to train and support coaches to be experts in all content areas. While web-based teacher professional development shows a great deal of potential for improving practice, research is in the early stages of determining how to best design these experiences to further teaching and learning. This article describes what educators are learning about designing a web-based literacy coaching program based on translating the Institute for Learning's Content-Focused Coaching program (Bickel, Berstein-Danis, & Matsumura, 2015) to an online format.