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Salary: USD 155,000 - 206,000 / annual
Datadog is seeking a Director of Recruiting Operations and Systems to lead the strategy, evolution, and execution of the technology, systems, and operating model powering hiring across the organization. This leader will oversee Recruiting Operations, Recruiting Technology, and AI Enablement for the recruiting team, managing a team that supports approximately 200 recruiters, sourcers, and coordinators.
In this role, you will define and execute long-term goals and roadmap for the recruiting tech stack to support efficiency, including systems, integrations, AI capabilities, automation, and operational workflows. You will lead multidisciplinary teams to transition from traditional recruiting operations to a progressive, AI-native approach. Applying product management principles, you will gather user feedback to drive experimentation, new tool investments, and workflow improvements.
Key responsibilities include establishing responsible AI governance while driving automation initiatives that improve recruiter productivity, hiring quality, and operational efficiency. You will partner with People Analytics teams to ensure recruiting system workflows provide data for critical business decisions and train recruiting teams on tool usage. Cross-functional collaboration with Recruiting, Engineering, IT, Security, Finance, People Technology, and executive stakeholders is essential to drive platform adoption, continuous improvement, and organizational change while ensuring compliance with global AI hiring regulations.
Datadog operates as a hybrid workplace, valuing office culture for relationships, collaboration, and creativity while enabling work-life harmony.
REQUIREMENTS:
- Significant leadership experience driving enterprise-scale recruiting operations, people technology, product management, business operations, or comparable platform organizations
- Proven success leading complex technology, systems, or operational transformation initiatives with measurable business impact
- Strong experience managing recruiting vendors and maintaining awareness of market solutions
- Deep expertise in ATS configuration, Workday-to-Greenhouse connections and data flows, API issue resolution, integrations, and low-code agentic or workflow automation tools such as Workato
- Strong analytical and systems-thinking skills with ability to translate data into product priorities and executive decisions
- Experience spotting trends in recruiting data and proposing team support strategies
- Experience leading both managers and individual contributors
- Exceptional communication and stakeholder management skills, with experience influencing senior leaders across multiple functions
- Passion for building scalable systems, developing high-performing teams, and creating exceptional user experiences through continuous improvement
