Role Overview

Datadog, the world's leading cloud monitoring and security platform, is seeking a Director, Sales Field Enablement to join our high-growth team in New York, New York. As we continue to dominate the observability and DevOps markets, we're scaling our Go-To-Market (GTM) enablement programs to empower sales and customer success teams worldwide. This leadership role offers the chance to shape the future of sales training at a hypergrowth SaaS leader.

Our Sales Enablement team transforms how field teams sell Datadog's cloud observability solutions, from infrastructure monitoring to application performance management. You'll lead talented Field Enablement Managers, partnering across Sales, Customer Success, Product Marketing, and Curriculum & Strategy to deliver measurable business impact. If you thrive in fast-paced environments and have a passion for developing sales talent in cloud technology, this is your opportunity to make a lasting impact.

Key Responsibilities at Datadog

• Lead and mentor a high-performing team of sales and customer success trainers executing world-class enablement programs for global field teams.
• Design and deliver ongoing field training through sales kickoffs, quarterly business reviews, live classroom sessions, interactive e-learnings, and innovative formats.
• Spearhead the evolution of the Field Enablement team from traditional facilitators to proactive, data-driven business partners who identify knowledge gaps and prescribe targeted solutions.
• Embed directly with go-to-market teams to gain deep understanding of regional selling realities and Datadog's competitive landscape in cloud monitoring.
• Collaborate with subject matter experts and Curriculum & Strategy teams to create engaging live training experiences and rigorously measure their business impact.
• Develop specialized one-to-one and one-to-few coaching programs targeting the most critical sales and sales leadership competencies.
• Serve as the authentic voice of the field, representing sales and customer success perspectives in cross-functional strategy sessions.
• Drive continuous improvement through agile methodologies, building minimum viable training 'products' and iterating based on field feedback and performance data.
• Plan and execute large-scale sales summits and enablement events for hundreds of professionals across Datadog's global organization.

Qualifications & Requirements

To succeed as Director, Sales Field Enablement at Datadog, you'll need:

• 8+ years of progressive work experience, including at least 4 years in sales enablement, Learning & Development, or equivalent roles teaching sales professionals.
• 3+ years of people management experience leading direct reports in highly complex, ambiguous, high-growth environments.
• Proven track record leading classroom-style instruction and developing comprehensive sales training curricula from scratch.
• Exceptional emotional intelligence with outstanding listening skills and genuine passion for helping sales professionals grow their careers.
• Demonstrated ability to tie enablement initiatives directly to quantifiable business outcomes like pipeline growth, win rates, and revenue attainment.
• Experience building and scaling enablement programs that support global sales organizations in SaaS or technology companies.
• Agile mindset with proven success iterating quickly, launching MVPs, and continuously improving based on data and feedback.

Bonus Qualifications: Previous experience as a seller or customer-facing rep, sales coaching expertise, high-growth SaaS background, and knowledge of DevOps, cloud technologies, or observability platforms.

Salary & Benefits

Datadog offers competitive compensation for our Director, Sales Field Enablement role in New York, NY, including base salary, unlimited performance bonus potential, and significant equity upside. Our comprehensive benefits package includes:

• Family health insurance coverage with multiple plan options
• Generous equity package with stock options
• Unlimited PTO and flexible work policies
• Fitness reimbursements up to $1,200/year
• Professional development stipend for conferences and certifications
• Commuter benefits and transportation allowances
• 401(k) matching with immediate vesting
• Paid parental leave for maternity and paternity
• Home office setup allowance and premium equipment

Why Join Datadog?

Datadog isn't just a monitoring platform—we're at the forefront of the cloud observability revolution, helping thousands of companies achieve digital resilience through our unified platform. As a Director, Sales Field Enablement, you'll:

• Work with the brightest minds in DevOps and cloud infrastructure.
• Drive real business impact in a company growing 50%+ YoY.
• Shape enablement strategy during our most exciting growth phase.
• Join a collaborative culture that values innovation, ownership, and results.
• Access unlimited career growth opportunities across our global organization.

Our New York headquarters puts you at the heart of tech innovation, with easy access to finance, media, and enterprise customers who power the digital economy.

How to Apply

Ready to elevate sales enablement at the world's leading observability platform? Apply now for the Director, Sales Field Enablement position at Datadog. Submit your resume and tell us why you're passionate about empowering sales teams to sell cutting-edge cloud monitoring solutions. Don't miss this chance to join a hypergrowth leader—positions like this fill quickly!

Datadog is an Equal Opportunity Employer committed to diversity. We celebrate different perspectives and are dedicated to creating an inclusive environment for all employees.