As online learning continues to grow and became an integral component of many higher education institutions, the role of leadership in guiding those online learning initiatives differs from institution to institution. This paper explores the experiences of leaders in centers for teaching and learning who have a role in online learning leadership at small, private colleges. With online learning being just one of my many roles for leaders, a phenomenological study was used to fully understand the perceptions of leaders in leading online initiatives. Findings from the voices of those leaders can inform approaches for other leaders in online learning.