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 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.

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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