Enablement Systems Engineer

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 workflow orchestration frameworks (e.g., Zapier, Workato)

• Experience applying AI/ML or LLM-based tools in practical business workflows (prompting, evaluation, guardrails, integration into systems)

• Strong problem-solving skills and comfort working with ambiguous or loosely defined requirements

• Strong communication skills. Ability to communicate technical concepts clearly to non-technical stakeholders and influence cross-functional partners

Why This Role Matters

This role is critical to scaling Enablement efficiently. By automating workflows, building AI-driven tooling, and optimizing systems, this role directly offsets the need for additional operational headcount across Sales and Technical Enablement—allowing teams to move faster, operate more consistently, and focus on higher-value strategic work.

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:

• Continuous career development and pathing opportunities for internal mobility

• Intra-departmental mentor and buddy program for in-house networking

• An inclusive company culture, ability to join our Community Guilds

• New hire stock equity (RSUs) and employee stock purchase plan (ESPP)

• Free global mental health benefit through Spring Health

• Generous global benefits

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

#LI-Hybrid

Datadog offers a competitive salary and equity package, and may include variable compensation. Actual compensation is based on factors such as the candidate's skills, qualifications, and experience. In addition, Datadog offers a wide range of best in class, comprehensive and inclusive employee benefits for this role including healthcare, dental, parental planning, and mental health benefits, a 401(k) plan and match, paid time off, fitness reimbursements, and a discounted employee stock purchase plan.

The reasonably estimated yearly salary for this role at Datadog is:

$78,000—$114,000 USD

About Datadog:

Datadog (NASDAQ: DDOG) is a global SaaS business, delivering a rare combination of growth and profitability. We are on a mission to break down silos and solve complexity in the cloud age by enabling digital transformation, cloud migration, and infrastructure monitoring of our customers’ entire technology stacks. Built by engineers, for engineers, Datadog is used by organizations of all sizes across a wide range of industries. Together, we champion professional development, diversity of thought, innovation, and work excellence to empower continuous growth. Join the pack and become part of a collaborative, pragmatic, and thoughtful people-first community where we solve tough problems, take smart risks, and celebrate one another. Learn more about #DatadogLife on Instagram, LinkedIn, and Datadog Learning Center.

Equal Opportunity at Datadog:

Datadog is proud to offer equal employment opportunity to everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, and other characteristics protected by law. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. Here are our Candidate Legal Notices for your reference.

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Any information you submit to Datadog as part of your application will be processed in accordance with Datadog’s Applicant and Candidate Privacy Notice. For information on our AI policy, please visit Interviewing at Datadog AI Guidelines.