The Team
- Our GTM Enablement team plays a critical role in equipping Datadog’s Sales and Customer Success organizations with the skills, knowledge, and tools they need to perform at the highest level. We partner closely across Curriculum, Product Marketing, Operations, and GTM leadership to ensure enablement translates into meaningful behavior change and performance improvement in the field.
What You’ll Do
- Deliver high-impact live and virtual leadership development programs for Sales and Customer Success leaders, including frontline managers and second-line leaders.
- Partner closely with the Sales Leadership Curriculum team to align on program goals, learning outcomes, and reinforcement approaches—serving as a thought partner on how curriculum is brought to life in the field
- Facilitate leadership-focused sessions such as manager onboarding, coaching skill development, change leadership, and execution excellence.
- Design and lead reinforcement experiences (e.g., manager roundtables, coaching labs, leader practice sessions) that help leaders apply concepts in real team scenarios.
- Serve as a trusted partner to Sales and CS leadership, building strong relationships and adapting delivery based on leader needs, maturity, and business context.
- Use data, leader feedback, and field observations to assess program effectiveness and recommend improvements to delivery and reinforcement.
- Act as a standard-bearer for leadership enablement delivery, modeling best-in-class facilitation, presence, and executive communication.
- Coach and influence other Field Enablement Managers—particularly senior trainers—on delivering effective leadership enablement and facilitating leader-level audiences.
- Support leadership enablement across global regions as needed, partnering with regional Field Enablement leaders to ensure consistency and quality.
Who You Are
- 8+ years of experience in sales enablement, sales leadership development, sales leadership, or a related GTM role, with significant experience delivering GTM leadership development.
- Proven experience facilitating sessions for Sales and Customer Success leaders, including frontline and second-line managers.
- Strong executive presence and facilitation skills—you are confident leading discussions with experienced leaders and navigating complex dynamics in the room.
- Deep understanding of the realities of sales leadership, including coaching, performance management, change management, and driving execution through teams.
- Highly collaborative and skilled at partnering cross-functionally, particularly with curriculum and senior GTM stakeholders.
- Comfortable using performance data, leader feedback, and qualitative insights to inform enablement delivery and recommendations.
- Excellent communicator who can simplify complex leadership concepts and drive clarity and action.
- Acts as a mentor and role model—raises the bar for peers and helps develop other enablement leaders.
- Familiarity with sales methodologies (e.g., MEDDICC, Command of the Message) and how leaders coach to them.
- Willing and able to travel approximately 30% of the time globally to deliver trainings.
- 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.
About Datadog:
- 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.
Equal Opportunity at Datadog
- 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.
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Privacy and AI Guidelines
- 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.
