Thomas Sobolik, one of Datadog's Engineering VPs, shared his career journey and insights on leadership, technology, and company culture in this edition of the Datadog Engineering Spotlight. Ivo Dimitrov, another Engineering VP, discussed his background as an engineering manager for top organizations, his transition to management, and what excites him about building distributed data systems at Datadog. Sobolik reflected on his 30-year career, starting with a passion for electrical engineering and software development, and transitioning from individual contributor to manager. He highlighted the importance of teamwork, innovation, and continuous learning in his role as a manager. Sobolik discussed his experience working with product teams, helping colleagues, and navigating the challenges of growing a company like Datadog. He emphasized the need for a balance between introducing new processes and respecting the existing substrate to avoid resistance. The interview also touched on the importance of humility, experimentation, and taking intelligent risks in the engineering culture at Datadog.