Manager, Sales Field Enablement - New York

The Team

As part of Datadog’s GTM Enablement organization, the Field Enablement team drives seller performance through world-class training, coaching, and scalable learning experiences. We partner closely with Sales Leadership, Product Marketing, and cross-functional teams to deliver live enablement that helps sellers ramp faster, execute consistently, and drive impact throughout the customer journey. Our mission is simple: empower Datadog’s sales teams to be confident, consultative, and quota-crushing.

The Opportunity

Datadog is scaling rapidly, and with that growth comes the need for high-impact enablement that supports onboarding, skills development, and sales excellence. As the Manager of Field Enablement, you’ll lead a team of Field Enablement Managers responsible for delivering engaging, results-driven training sessions across the global sales org—while continuing to roll up your sleeves and facilitate programs yourself.

This is a player-coach role: you’ll split your time between managing a team and directly engaging with sellers. You’ll work cross-functionally with Sales, Enablement, and Product stakeholders to align programming with business needs and drive consistency in the field.

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

• Manage, coach, and develop a team of Field Enablement Managers responsible for delivering onboarding and continuous sales training
• Facilitate live training sessions (virtually and in person) for sellers, with a focus on sales methodology, product positioning, discovery, value selling, and competitive differentiation
• Oversee planning and execution of regional and global sales workshops, onboarding programs, and ad hoc training requests
• Partner with Curriculum and Program teams to co-create and scale new training initiatives across segments and regions
• Build strong relationships with Sales Leadership to surface skill gaps, gather field feedback, and shape enablement priorities
• Define and track enablement success metrics that align with seller performance and business outcomes
• Champion a high-quality, engaging learner experience across all live sessions
• Contribute to hiring, onboarding, and performance management within the enablement team, fostering an inclusive and collaborative team culture

Who You Are

• 5–7+ years of experience in sales, sales enablement, or revenue-focused learning and development, with at least 1–2 years of experience leading or mentoring others
• A confident facilitator with excellent communication and presentation skills—comfortable in front of groups, whether live or virtual
• Passionate about coaching and empowering others to succeed
• Skilled at building trust and alignment with cross-functional partners and sales leaders
• Data-driven, with the ability to connect training programs to business performance
• Experienced in high-growth SaaS or tech environments with a fast-moving sales organization 
• Based in New York City and able to work in a hybrid in-office/remote model

Bonus Points

• Experience leading onboarding or enablement for Commercial, Mid-Market, or Enterprise sales teams
• Familiarity with sales methodologies (e.g. MEDDIC, Challenger, Command of the Message)
• Background in adult learning, facilitation, or instructional design 
• Experience leading enablement programs globally or across multiple sales segments

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.

Benefits and Growth

• High income earning opportunities based on individual performance
• New hire stock equity (RSUs) and employee stock purchase plan (ESPP)
• Continuous professional development, product training, and career pathing
• Sales training in MEDDIC and Command of the Message
• Intradepartmental mentor and buddy program for in-house networking
• An inclusive company culture, ability to join our Community Guilds (Datadog employee resource groups)
• Access to Inclusion Talks, our Internal panel discussions
• Free, global Spring Health benefits for employees and dependents age 6+
• Competitive global benefits
• Giving programs

Benefits and Growth listed above may vary based on the country of your employment and the nature of your employment with Datadog.