Field Enablement Manager (Customer Success)

The Team Our GTM Enablement team is a unique strategy and curriculum team that plays an integral part in connecting our go-to-market approach and curriculum to customer value. We’re interdisciplinary thinkers leveraging diverse business backgrounds in engineering, education, management consulting, business operations (and more!) to define, manage and measure Datadog’s global go to market motion. We empower all of Datadog’s customer-facing teams with the right information, skills, and tools at the right time in order to maximize their ability to land, expand and drive Datadog’s next phase of growth. The Opportunity: Datadog continues to grow at a rapid rate, and with this exciting growth, our onboarding and ongoing enablement programs are also increasing in scale and complexity. This position is part of a dynamic Field Enablement team responsible for delivering onboarding and ongoing enablement training and programs for all of our Sales and Customer Success teams . At the same time, this role will specialize in supporting our Post-Sales Customer Success teams across the Americas . We’re looking for a structured communicator and facilitator with strong business acumen and a knack for simplifying complex concepts. You’ll deliver engaging, practical learning experiences that help Customer Success Managers apply key skills in their day-to-day work. The primary focus of this role is to deliver, facilitate, and reinforce existing enablement programs while partnering closely with Customer Success leaders, the Curriculum team, and other enablement stakeholders to identify performance gaps, tailor programs to regional needs, and strengthen behaviors that drive results. You’ll use data, feedback, and qualitative insights to identify where teams need the most support, curate relevant enablement resources, and design hands-on reinforcement activities that help sellers apply what they’ve learned in real-world scenarios. At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. What You’ll Do Deliver engaging live and virtual enablement sessions for global Sales and Customer Success teams, including onboarding, ongoing training, and reinforcement programs. Partner with Customer Success and GTM leaders across the Americas to identify performance trends and development needs using sales data, field observations, and stakeholder feedback. Collaborate closely with the Curriculum team to share field insights, validate program effectiveness, and ensure enablement content aligns with the needs of Customer Success Managers. Curate and adapt existing enablement materials to ensure content relevance for regional and segment-specific needs, with a focus on Customer Success motions. Design and facilitate reinforcement activities such as deal clinics, role plays, and skill application workshops to help teams apply core concepts in their daily workflow. Track participation, collect feedback, and analyze results to measure enablement effectiveness and recommend improvements. Build trusted relationships with Sales and Customer Success stakeholders to understand business priorities, diagnose challenges, and identify appropriate enablement interventions. Act as a connector between the field and internal enablement —surfacing field insights that inform future program development and execution. Who You Are 3–5 years of experience in sales enablement, specializing in field enablement and training delivery Experience supporting GTM Teams in a SaaS or technology company is preferred, but not required Strong business acumen and ability to interpret performance data (e.g., pipeline health, conversion rates, adoption metrics) to identify enablement opportunities. Experienced facilitator skilled in leading engaging, discussion-driven sessions for experienced ... (truncated, view full listing at source)