This episode explores the challenges and strategies of leading a large, publicly traded B2B software company, specifically HubSpot, as its CEO. Against the backdrop of Yamini Rangan's transition into the CEO role, the discussion delves into the complexities of navigating founder involvement and maintaining deep conviction in the face of market pressures. More significantly, the conversation highlights HubSpot's counterintuitive approach to AI monetization, emphasizing customer value over immediate revenue maximization. For instance, the discussion contrasts outcome-based pricing with HubSpot's chosen strategy of integrating AI into its existing platform and monetizing the entire platform. As the discussion pivoted to leadership, Rangan emphasizes the importance of aligning resources across different organizational functions to achieve strategic goals. Finally, the interview concludes with Rangan's insights on the transformative potential of AI for SMBs, the competitive landscape with Salesforce, and the evolving nature of digital marketing in the age of AI-powered search.