Stephen is the Senior Director of Technical Support Engineering, EMEA at Datadog, where he leads regional support operations to ensure customers maximise value from Datadog’s observability and security platform. Known for building high-performing teams and driving operational excellence, he brings extensive experience in scaling international support, onboarding, and deployment functions across fast-growing technology companies. Before joining Datadog, he spent over nine years at Rapid7, progressing from Senior Technical Support Manager to Senior Director of International Support, Onboarding & Deployment. In these roles, he led multi-regional teams, enhanced customer experience programs, and implemented strategies that improved efficiency, responsiveness, and cross-functional collaboration. Stephen's career reflects a commitment to empowering teams, delivering measurable business impact, and helping customers succeed at scale.