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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.
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.
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.
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 sales and customer success professionals.
Collaborative and relationship-oriented—you build credibility quickly with Sales and Customer Success leaders, sellers, and cross-functional partners
Familiarity with sales methodologies such as MEDDICC or Command of the Message.
Foundational understanding of Datadog’s core product pillars (Infrastructure, APM, Logs) and the ability to connect technical product capabilities to customer outcomes.
Organized, detail-oriented, and proactive—able to manage multiple programs and adapt to evolving business priorities.
Clear and confident communicator who can simplify complex technical and business topics for diverse audiences.
Scrappy and entrepreneurial: You enjoy building and iterating, and don’t mind getting messy
This role may require up to 30% travel
Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's okay. If you’re passionate about technology and want to grow your skills, we encourage you to apply.
Generous and competitive benefits package
New hire stock equity (RSUs) and employee stock purchase plan
Continuous career development and pathing opportunities
Employee-focused best in class onboarding
Internal mentor and cross-departmental buddy program
Friendly and inclusive workplace culture
Benefits and Growth listed above may vary based on the country of your employment and the nature of your employment with Datadog.
#LI-Hybrid
Datadog offers a competitive salary and equity package, and may include variable compensation. Actual compensation is based on factors such as the candidate's skills, qualifications, and experience. In addition, Datadog offers a wide range of best in class, comprehensive and inclusive employee benefits for this role including healthcare, dental, parental planning, and mental health benefits, a 401(k) plan and match, paid time off, fitness reimbursements, and a discounted employee stock purchase plan.
The reasonably estimated yearly salary for this role at Datadog is:
$86,000—$127,000 USD
Datadog (NASDAQ: DDOG) is a global SaaS business, delivering a rare combination of growth and profitability. We are on a mission to break down silos and solve complexity in the cloud age by enabling digital transformation, cloud migration, and infrastructure monitoring of our customers’ entire technology stacks. Built by engineers, for engineers, Datadog is used by organizations of all sizes across a wide range of industries. Together, we champion professional development, diversity of thought, innovation, and work excellence to empower continuous growth. Join the pack and become part of a collaborative, pragmatic, and thoughtful people-first community where we solve tough problems, take smart risks, and celebrate one another. Learn more about #DatadogLife on Instagram, LinkedIn, and Datadog Learning Center.
Datadog is proud to offer equal employment opportunity to everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, and other characteristics protected by law. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. Here are our Candidate Legal Notices for your reference.
Datadog endeavors to make our Careers Page accessible to all users. If you would like to contact us regarding the accessibility of our website or need assistance completing the application process, please complete this form. This form is for accommodation requests only and cannot be used to inquire about the status of applications.
Any information you submit to Datadog as part of your application will be processed in accordance with Datadog’s Applicant and Candidate Privacy Notice. For information on our AI policy, please visit Interviewing at Datadog AI Guidelines.
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Datadog is a cloud monitoring and observability platform that aggregates metrics, logs, and traces from applications, infrastructure, and third-party services. The SaaS company serves DevOps, engineering, and operations teams across enterprises of all sizes who need real-time visibility into their systems' performance and health.
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