Enablement Systems Engineer Careers at Datadog - New York, New York

Role Overview

Join Datadog's innovative Go-to-Market Enablement & Business Value team as an Enablement Systems Engineer in New York, New York. This critical role focuses on configuring, maintaining, and evolving enablement systems with a strong emphasis on automation, scalability, and operational efficiency. You'll partner with GTM Enablement stakeholders, Sales Operations, RevOps, IT, and technical teams to deliver system-driven solutions that reduce manual effort and accelerate impact across Sales and Technical teams.

Datadog, the leading cloud monitoring and security platform, empowers you to scale Sales and Technical Enablement through cutting-edge systems, AI-driven tooling, and workflow automation. Operating in a hybrid workplace, you'll contribute to Datadog's next phase of growth while enjoying work-life harmony in the heart of New York City.

This position is perfect for engineers passionate about DevOps automation, observability engineering, and building internal tools that drive business value. Leverage your expertise in Python, JavaScript, APIs, and platforms like Zapier or Workato to transform enablement operations at a hyper-growth SaaS leader.

Key Responsibilities at Datadog

As an Enablement Systems Engineer, you'll drive operational excellence through technology. Key responsibilities include:

• Automate workflows: Identify and eliminate manual, repetitive processes across Sales Enablement, Technical Enablement, and GTM teams using Python and JavaScript.
• Build end-to-end automations: Own lifecycle automations, system integrations, alerts, and cross-platform workflows for maximum efficiency.
• Implement AI tooling: Design AI-powered solutions for content discovery, learning reinforcement, deal support, coaching insights, and enablement analytics.
• Manage enablement platforms: Configure, administer, and onboard LMS, Sales Recording, and GTM tools ensuring seamless adoption and measurable ROI.
• Collaborate cross-functionally: Translate business requirements into scalable technical solutions with Sales Ops, RevOps, IT, Data, and Product teams.
• Ensure system reliability: Act as technical owner maintaining security, scalability, and ease-of-use for all enablement infrastructure.
• Modernize legacy systems: Reduce technical debt by simplifying workflows and proactively improving automations.
• Drive metrics & reporting: Measure impact through time saved, headcount avoided, adoption rates, and enablement effectiveness KPIs.
• Establish best practices: Create standards for documentation, testing, monitoring, and support of enablement tooling.

Your work will directly contribute to Datadog's observability platform success by empowering customer-facing teams with the right tools at the right time.

Qualifications & Requirements

Datadog seeks proven technical talent with enablement systems expertise:

• BS/MS in Computer Science, Engineering, or related field (or equivalent experience)
• 2-3+ years building automation, internal tools, or workflow systems in production
• Strong programming in Python, JavaScript, or similar languages
• Hands-on API integration and cross-platform workflow experience
• Experience with LMS platforms, Sales Recording tools (Gong, Chorus), or Enablement platforms
• Familiarity with automation platforms like Zapier, Workato, or workflow orchestration frameworks
• Practical experience applying AI/ML or LLM tools in business workflows
• Excellent problem-solving with ambiguous requirements
• Strong communication translating technical concepts for non-technical stakeholders

Bonus: Experience with Datadog monitoring, cloud observability, or sales tech stacks.

Salary & Benefits

Datadog offers competitive compensation for Enablement Systems Engineers in New York:

• Salary Range: $135,000 - $175,000 base (depending on experience)
• Competitive equity package with stock options
• Comprehensive health insurance for individuals and families
• Commuter benefits and transit subsidies
• Fitness reimbursements and gym memberships
• Professional development stipend for certifications and conferences
• Unlimited PTO and flexible hybrid work
• 401(k) matching and retirement planning
• Parental leave and family support programs
• Wellness programs including mental health resources

Why Join Datadog?

Datadog is the essential monitoring and security platform for cloud applications, trusted by thousands of innovative companies worldwide. As an Enablement Systems Engineer, you'll:

• Work with cutting-edge observability, DevOps, and AI technologies
• Impact global GTM strategy at hyper-growth scale
• Collaborate in New York's vibrant tech ecosystem
• Enjoy hybrid flexibility with strong office culture
• Grow your career through internal mobility and development
• Contribute to products that developers love

Datadog's interdisciplinary Enablement team combines engineering, education, and business expertise to drive customer value and revenue growth.

How to Apply

Ready to automate the future of sales enablement at Datadog? Apply now for the Enablement Systems Engineer position in New York, New York. Submit your resume and tell us how you've driven operational efficiency through automation. Join thousands of Datadogs building the world's best cloud monitoring platform.

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