Several, large-scale quantitative studies suggest virtual coaching is an effective professional development strategy capable of producing similar results as face-to-face (F2F) programs. Virtual coaching can also be cost-effective, convenient, and even essential when in-person learning is disrupted. However, existing research offers few descriptions of how virtual coaching practices differ from F2F or what modifications coaches must make. To date, no studies have explored virtual coaching for technology integration, which likely has different purposes and more non-directive approaches than existing studies. To address this gap, this case study documents an organization's first-time transition from F2F to online instructional technology coaching, with an in-depth focus on one coach's experiences. Findings offer proof-of-concept that virtual technology coaching can be successful, but coaches must overcome challenges associated with enrollment, sustaining relationships, and adapting technologies to coaching purposes. Additionally, a strong grounding in the coaching literature is a necessary precursor for success.