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Gogo, the inflight Internet company, recently underwent significant transformation. The ecosystem for business operation had shifted rapidly. These changes required the company to quickly adapt elements of its business strategy to increase focus on both innovation of new technology and mature operational practices in order to grow and scale the business globally. To enable these changes, the way employees worked together inside the organization also needed to be transformed. This was the impetus to change the PM process. At its core, the philosophy driving Gogo’s changes to PM centered on building a culture of agility. Internal research in partnership with leaders, people managers, and individual contributors was conducted along with external research. Based on the findings from this research, PM practices were redesigned to focus on changes in four key areas: (1) creating a feedback-rich environment; (2) ensuring focus and alignment on meaningful goals; (3) building a cadence for reflection and planning at both the organization and group levels and between employees and their managers; and (4) enabling a culture of development. This case provides insight into the first 2 years of Gogo’s journey—beginning with the discovery process and continuing through the design, implementation, and evaluation (inclusive of ongoing adaptation). Throughout the process, significant time and energy were invested in stakeholder engagement, which was imperative for making significant cultural change stick.