Director Learning Enablement Jobs (NOW HIRING)

The GTM Enablement & Business Value Operations team is the center of excellence responsible for how go-to-market execution is designed, enabled, measured, and continuously improved across Sales Enablement, Technical Solutions Enablement, and Business Value.

As Director, GTM Enablement Operations, you will lead the center of excellence and build the operational foundation that enables this organization to scale. You will lead the Operations and Systems & Analytics teams, establishing the operating model, technology capabilities, analytics, governance, and business processes that support every enablement program across the organization.

You will also serve as the Operations Leader for GTM Enablement's largest cross-functional initiatives—including Sales Kickoff (SKO), Technical Sales Kickoff (TSKO), and other enterprise programs—ensuring they are planned, governed, and executed with operational excellence.

Success in this role is measured by the organization's ability to scale. The outcome is an operating model that enables GTM Enablement & Business Value to continuously improve execution, adopt new technologies, leverage AI effectively, and demonstrate business impact.

What You'll Do:Build the GTM Enablement & Business Value Operating Model

Design and evolve the operational foundation for GTM Enablement & Business Value. Establish the governance, planning processes, operational cadence, portfolio management, and delivery standards that enable the organization to execute consistently at scale.

Build Technology Capabilities That Scale

Lead the Systems & Analytics organization responsible for enablement technology, learning systems, content management, reporting, analytics, automation, and AI-enabled workflows. Partner with Enablement & Business Value leadership to evaluate, implement, and optimize technologies that improve productivity, learning, and business performance.

Build Operational Insight

Develop the operational measurement framework that enables leaders to understand organizational health, capacity, program effectiveness, productivity, and business impact. Deliver dashboards and reporting that improve planning, prioritization, and investment decisions.

Lead Enterprise Program Operations

Serve as the Operations Leader for GTM Enablement's largest cross-functional initiatives, including SKO, TSKO, enterprise launches, and other strategic programs. Build the operational frameworks that enable complex initiatives to be planned, governed, and delivered successfully across multiple organizations.

Advance AI & Technology Innovation

Partner with GTM Enablement leadership to identify where AI and emerging technologies can create meaningful organizational leverage. Evaluate new platforms, operationalize AI-enabled workflows, establish governance and best practices, and help the organization adopt new capabilities responsibly and effectively.

Build a High-Performing Organization

Lead and develop the Operations and Systems & Analytics teams while fostering a culture of operational excellence, innovation, accountability, and continuous improvement. Build strong partnerships across the business and create capabilities that increase the effectiveness of every enablement team.

Who You Are:

• 10+ years leading Operations, Enablement Operations, Revenue Operations, Business Operations, Program Management, or similar functions in a high-growth SaaS organization.
• Proven experience building operating models, governance frameworks, and scalable business processes that improve organizational effectiveness.
• Experience leading multiple operational disciplines, including operations, systems, analytics, business intelligence, or program management.
• Experience selecting, implementing, and optimizing enterprise technologies that support learning, enablement, collaboration, and operational excellence.
• Strong understanding of enablement technologies, including Learning Management Systems (LMS), Content Management Systems (CMS), knowledge management platforms, workflow automation, business intelligence, and analytics platforms.
• Experience evaluating and implementing AI-enabled technologies that improve learning, content development, coaching, analytics, and operational productivity.
• Hands‑on expertise with enterprise AI platforms such as Claude, ChatGPT, and other large language models, with a practical understanding of prompt engineering, governance, workflow design, and organizational adoption.
• Experience leading enterprise-wide initiatives involving executive stakeholders and multiple cross-functional organizations.
• Strong executive communication, organizational leadership, and stakeholder management skills.
• A builder who enjoys creating capabilities that enable organizations to scale.
• Bachelor's degree required.
• MBA or other advanced degree preferred

Preferred Experience:

• Experience supporting Sales, Technical Solutions, or Customer Success organizations.
• Experience with platforms such as Docebo, Gong, Asana, Tableau, or similar enterprise technologies.
• Experience planning and delivering enterprise initiatives such as Sales Kickoff (SKO), organizational transformations, technology implementations, or global enablement programs.
• Experience introducing AI into business workflows and driving organizational adoption.

Benefits & Growth:

• Generous and competitive benefits package
• New hire stock equity (RSUs) and employee stock purchase plan
• Continuous career development and pathing opportunities
• Employee-focused best in class onboarding
• Internal mentor and cross-departmental buddy program
• Friendly and inclusive workplace culture

#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:

$203,000 — $270,000 USD

About Datadog:

Datadog is the leading observability and security platform for the AI era, providing businesses with unified visibility across the technology stack to manage complexity at scale. It brings applications, infrastructure, data, models, and security into one place, using AI to detect and resolve issues before they impact customers. Trusted globally by Fortune 500 companies and high-growth AI leaders, Datadog enables businesses to move faster with clarity and confidence. 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.

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