Enablement Systems Engineer

The Team:

Our Go-to-Market (GTM) Enablement & Business Value team plays an integral part in connecting our go-to-market approach to customer value. We’re interdisciplinary thinkers leveraging diverse business backgrounds in engineering, education, management consulting, business operations (and more!) to define, manage and measure Datadog’s global go-to-market motion. We empower all of Datadog’s customer-facing teams with the right training, skills, and tools at the right time in order to maximize their ability to drive Datadog’s next phase of growth. 

The Opportunity:

At Datadog, the Enablement Systems Engineer plays a critical role on the Enablement Operations team, supporting our global Go-to-Market (GTM) Enablement & Business Value function. This role is responsible for configuring, maintaining, and evolving our enablement systems and tool stack, with a strong focus on automation, scalability, and operational efficiency.

In this role, you will partner closely with GTM Enablement stakeholders, as well as Sales Operations, RevOps, Internal Analytics, IT, and Sales & Technical Solutions teams, to design and deliver scalable, system-driven solutions that reduce manual effort and accelerate enablement impact across Sales and Technical teams.

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:

You will be responsible for scaling Sales and Technical Enablement through systems, automation, and AI-driven tooling—reducing manual effort, improving speed to impact, and increasing operational efficiency across Enablement teams.

Specifically, you will:

• Identify, design, and automate manual, repetitive, and error-prone enablement workflows across Sales Enablement, Technical Enablement, and GTM teams
• Build and own end-to-end automated workflows across systems,alerts, integrations, and lifecycle automations
• Design and implement AI-powered tooling to support GTM teams (e.g., content discovery, learning reinforcement, deal support, coaching insights, enablement analytics)
• Configure, administer, integrate, and onboard new enablement and GTM tools, ensuring seamless adoption and measurable business impact
• Partner closely with Enablement, Sales Ops, RevOps, IT, Data, and Product teams to translate business workflows into scalable technical solutions
• Act as a technical owner for enablement systems, ensuring reliability, security, scalability, and ease of use
• Reduce technical debt by modernizing legacy workflows, simplifying system sprawl, and proactively improving existing automations
• Establish best practices for documentation, testing, monitoring, and support of enablement tooling
• Measure and communicate impact through metrics such as time saved, headcount avoided, adoption, and enablement effectiveness
• Conduct ad-hoc GTM enablement owned systems reporting
• Complete data entry tasks (migrate records between systems, upload data, mass data changes via API or system upload)
• Assist broader GTM Enablement team in content creation, configuration, net new use case builds leveraging toolstack

Who you are:

• BS or MS in Computer Science, Engineering, or a related technical field (or equivalent practical experience)
• 2-3 years of experience building automation, internal tools, or workflow systems in a production environment
• Strong programming skills in one or more of the following: Python, JavaScript, or similar languages
• Hands-on experience working with APIs, system integrations, and cross-platform workflows
• Experience with LMS, Sales Recording, or Enablement platforms
• Familiarity with automation platforms, low-code/no-code tools, or workfl