Henry Schuck, CEO of ZoomInfo, offers insights on a crucial challenge faced by CEOs of Series B companies: deciding whether to uplevel internal leaders or hire externally. As businesses evolve, the demands on leadership change significantly. Schuck emphasizes the importance of assessing what the company needs in the near term—specifically, over the next 12 to 24 months. He points out that leaders must not only understand their role but also adapt quickly to the company’s growth in scale and complexity. Schuck shares his experiences with promoting first-time executives and the necessity of making tough decisions when someone isn’t fitting their role anymore. Delaying such decisions can have negative effects on the team, customers, and the overall business. He advises being respectful in communication during transitions and ensuring that departing leaders are supported in finding their next opportunity. This approach maintains team morale and sets a standard of performance for the organization. When considering external hires, Schuck warns against common pitfalls. Candidates from large companies may struggle in a startup environment due to a lack of necessary infrastructure and may not align with the company’s values. Successful internal promotions depend on the leader’s self-awareness, willingness to learn, and existing trust within the organization. However, these internal bets often require more hands-on support initially to help them succeed in their new roles.