Role Overview

Join Datadog's innovative GTM Enablement team as a Senior Field Enablement Manager - Leadership Development in New York City. Datadog, the leading cloud monitoring and security platform, empowers Sales and Customer Success organizations with cutting-edge skills, knowledge, and tools for peak performance. This senior, highly visible role focuses on delivering Sales and Customer Success leadership development enablement, equipping frontline and second-line leaders with essential coaching, change management, and execution skills.

Reporting to the Director of Field Enablement, you'll partner with the Sales Leadership Curriculum team to translate curriculum into impactful field experiences. Set the global standard for leadership enablement while driving behavior change and performance improvement across Datadog's observability platform ecosystem. Ideal for experienced enablement leaders passionate about Datadog careers in sales enablement and cloud observability leadership.

Key Responsibilities at Datadog

• Deliver high-impact live and virtual leadership development programs for Sales and Customer Success leaders at all levels.
• Collaborate closely with the Sales Leadership Curriculum team as a thought partner on program goals, outcomes, and field reinforcement.
• Facilitate critical sessions including manager onboarding, coaching skill development, change leadership, and execution excellence.
• Design innovative reinforcement experiences such as manager roundtables, coaching labs, and real-world leader practice sessions.
• Serve as a trusted advisor to Sales and CS leadership, building relationships and customizing delivery based on business needs.
• Leverage performance data, leader feedback, and field observations to measure impact and drive continuous improvement.
• Act as the standard-bearer for leadership enablement, modeling elite facilitation and executive communication skills.
• Coach senior Field Enablement Managers globally, elevating delivery standards across regions.
• Support international leadership enablement efforts, ensuring consistency and quality worldwide.

Qualifications & Requirements

• 8+ years in sales enablement, leadership development, sales leadership, or GTM roles with proven GTM leadership program delivery.
• Direct experience facilitating for Sales and CS leaders, handling frontline managers and second-line executives.
• Executive presence and masterful facilitation skills for complex leader discussions and group dynamics.
• Deep expertise in sales leadership challenges: coaching, performance management, change leadership, and execution.
• Proven cross-functional collaboration, especially with curriculum teams and senior GTM stakeholders.
• Strong analytical skills using data, feedback, and insights to optimize enablement strategies.
• Exceptional communication simplifying complex leadership concepts into actionable insights.
• Mentorship mindset to develop peer enablement leaders and raise performance bars.

Experience in cloud monitoring platforms like Datadog, observability, DevOps, or SaaS GTM environments strongly preferred.

Salary & Benefits

Datadog offers competitive compensation for Senior Field Enablement Manager roles in New York, typically ranging from $165,000 to $225,000 base salary plus bonuses, equity, and comprehensive benefits. Enjoy family health insurance, commuter benefits, fitness reimbursements, and professional development support. Additional perks include unlimited PTO, 401(k) matching, parental leave, and wellness programs tailored for high-performers in the observability and cloud security space.

Why Join Datadog?

Datadog is the fastest-growing cloud observability platform, trusted by thousands of innovative companies for monitoring, security, and analytics. As a public company, we offer unmatched growth opportunities in New York tech careers. Work with world-class teams driving DevOps, SRE, and GTM excellence. Our culture emphasizes innovation, collaboration, and impact—perfect for leadership development professionals passionate about scaling sales success in cloud-native environments.

Thrive in a dynamic setting where your enablement expertise directly accelerates Datadog's mission to help DevOps teams monitor and secure modern applications. Access cutting-edge tools, global reach, and a supportive community focused on continuous learning and leadership growth.

How to Apply

Ready to elevate sales leadership at Datadog? Apply now for this Senior Field Enablement Manager position in New York City. Submit your resume highlighting GTM leadership development experience and facilitation achievements. Join our mission to power the most observant companies in the world. Datadog is an equal opportunity employer committed to diversity.

This role offers hybrid flexibility in NYC with opportunities for global impact. Don't miss your chance to shape the future of sales enablement at a cloud monitoring leader.