Senior Field Enablement Manager - Leadership Development

Location: New York City
Reports to: Director, Field Enablement

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.

Within this organization, Field Enablement focuses on bringing enablement to life—delivering, reinforcing, and contextualizing programs in close partnership with Sales and CS leaders. Leadership Development is a core pillar of this work as we continue to scale and invest in strong, consistent sales leadership across Datadog.

The Opportunity

Datadog is looking for a Senior Field Enablement Manager to lead the delivery of Sales and Customer Success leadership development enablement as part of the Global Field Enablement Team. This role will focus on enabling frontline and second-line leaders with the skills, behaviors, and mindset required to coach effectively, lead teams through change, and drive consistent execution across the GTM organization.

This is a senior, highly visible role designed for an experienced enablement leader who has deep experience delivering leadership development programs as a trainer and facilitator. You will serve as a core partner to the Sales Leadership Curriculum team, helping translate curriculum into impactful, high-quality learning experiences for leaders in the field.

In addition to delivering leadership enablement, this role will help set the standard and uplevel how leadership enablement is delivered across Field Enablement globally —coaching and influencing other senior field trainers and raising the bar for how we engage, challenge, and develop Sales and CS leaders at Datadog.  

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.