Candace Shamieh's piece delves into the roles of Bella Barbera and Emilio Rodriguez, two Customer Success Sales Engineers (CSSEs) at Datadog who transitioned from nontraditional backgrounds into sales engineering, highlighting their contributions to the company's Sales Engineering team. Bella, previously a mechanical engineer, shifted her career focus to software by enhancing her technical skills through self-directed learning, ultimately finding her niche in the collaborative and problem-solving aspects of sales engineering. Emilio, initially a Customer Success Associate, sought to deepen his technical knowledge to provide more comprehensive customer support, leveraging mentorship and self-directed study to transition into his current role. Both individuals exemplify Datadog's culture of curiosity, continuous learning, and cross-functional collaboration, contributing to customer success and the growth of the Sales Engineering team through leadership, innovative problem-solving, and cross-cultural engagement. Their journeys underscore the value Datadog places on initiative and adaptability, encouraging others to consider careers in a dynamic, supportive environment.