Executives at large health systems across the United States have an interest in developing or expanding telehealth programs. While interest is increasing, telehealth implementation teams (or e-health teams) often face challenges that can hinder the successful transition from pilot to full-scale implementation. Here we share lessons learned by four large health systems that have faced and largely surmounted these challenges. For e-health teams to successfully engage senior leaders in new telehealth initiatives, it is essential to align proposals with the strategic goals of the institution and use patient stories to highlight the benefits of telehealth. To manage the demand for telehealth offerings from patients and dozens of clinical departments, e-health teams should develop a framework for deciding what's most important. To get large medical staffs to adopt telehealth workflows, e-health teams should nurture telehealth champions at each staff level and incentivize them with career development opportunities and rewards. To enroll a heterogeneous population of patients in telehealth programs, e-health teams should use multiple methods of education to accommodate different learning styles. And finally, health systems should develop telehealth-specific outcome measures and repeatedly use them to motivate improvement.