Enablement Designer, Recruiting and People – Contractor (12-Month Engagement)

Datadog is looking for a contract Enablement Designer for Recruiting and People to build and deliver the training content for our global team over a 12-month engagement. This is a hands-on build-and-facilitate role: you will design curriculum, produce content, and run live training for recruiters, sourcers, coordinators, and people leaders across our global sites. This engagement is scoped around content, design, and delivery. Overall program ownership, roadmap, and long-term governance sit with Recruiting Operations leadership, who you will report to and partner with closely. Your job is to build the material and get it into people’s hands — and to leave behind a documented, maintainable system when the engagement ends. 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: Design and build modular enablement content across the recruiting lifecycle: intake, sourcing, assessment, closing, candidate experience, systems. Produce it to a publishable standard: facilitator guides, participant materials, job aids, async modules, knowledge checks, and the LMS and SCORM packaging that gets them live. Facilitate the core curriculum on an agreed cadence, including regional delivery. Build the measurement layer: completion, confidence, and manager-reported readiness against a baseline. Contribute the AI layer into existing manager development rather than building a parallel leader track. Leave a maintainable content model: source files, owners, review cadence, update triggers. Who You Are: 5+ years in Talent Acquisition, Enablement, Learning & Development, or instructional design, with meaningful time inside or directly supporting a recruiting function A prolific content builder — you can point to curricula, playbooks, and training materials you personally designed and shipped A confident facilitator who can hold a room of experienced recruiters, in person and virtually Fast to ramp and comfortable operating with limited hand-holding; you can walk into a new organization, diagnose the gaps, and start producing Experienced working as a contractor or consultant, with a track record of scoped delivery against a timeline Skilled at building credibility quickly with stakeholders you do not manage Comfortable designing for a global audience across the Americas, EMEA, and APAC Experienced developing or coaching people leaders is a strong plus What This Role Is Not: Ownership of the overall Recruiting Enablement program, roadmap, or budget — that remains with Recruiting Operations leadership People management or headcount ownership Ongoing operational support for recruiting systems or processes 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: Generous and competitive benefits package New hire stock equity (RSUs) and employee stock purchase plan (ESPP) Continuous career development opportunities Product training to develop understanding of our product and space Best in breed onboarding Internal mentor and buddy program cross-departmentally Friendly and inclusive workplace culture 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: $131,000 — $164,000 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 cust