This case study follows Ritu Narayan, founder and CEO of Zum, as she redefines student transportation by applying a technology-driven approach to an industry that had seen little modernization. Zum evolved from a consumer-facing rideshare marketplace—launched by Narayan to address a problem she knew intimately as a working parent—into a transportation partner to the largest public school districts in the country, and ultimately into a leader in modernizing school bus fleets through electrification. This path required Narayan to pivot the company multiple times, making bold moves and difficult decisions. The case examines the technological transformation Zum brought to student transportation, including the introduction of dynamic route optimization, real-time bus tracking, and RFID-based student check-in systems, which set a new standard for safety and transparency.