This case asks how startup founders make scaling decisions in light of their priorities for their business and for themselves. Otto was a technology company that applied artificial intelligence technology to sales. It deployed natural language processing to find sales targets for companies, write messages for those targets, and send them over email, social media, and other means. Otto's automated sales outreach was personalized at scale and improved results for its clients. Early in 2024, its founders had to decide how to scale their business. They had three options: they could focus on business-to-business sales for individual clients, which posed the specific challenge of growing while working with large customer organizations; they could concentrate on the financial services field, in which they sourced deals for private equity companies and investment banks; or they could sell Otto to a larger sales firm.