Lesson 1: The loosening of federal government regulations enabled the rapid scaling of telehealth, as it enabled providers to be reimbursed for video visits at the same rate as in-person services. Lesson 2: While resistance to change was the norm, the COVID-19 crisis motivated improvements to four major internal operational workflows (scheduling, appointment conversions, patient support and Virtual Rooming Assistants) for video visits, which were met with acceptance by both clinical and non-clinical staff. Lesson 3: Leveraging prior intraorganizational relationships and active collaboration between different stakeholders, helped drive rapid operational change. An ongoing centralized communication and support strategy, ensured all stakeholders were informed and engaged during these uncertain times. Lesson 4: Regular electronic health record (EHR) training and educational material increased end-user knowledge of video visits and helped ensure the visit was safe, medically effective and maintained patient-provider relationships. Lesson 5: A clearly defined intake and evaluation process to filter out technologies that do not integrate with the patient portal or the EHR, ensures operational consistency and long-term sustainability. Lesson 6: Personalized support to patients of different levels of technical literacy with using the preferred patient portal and application, was vital to its use, adoption and overall patient experience.