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Director, Recruiting Operations

Datadog· People / Recruiting
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Hybrid (Boston, MA / New York, NY), Hybrid (Remote), Hybrid (Various US locations)$200k - $245kfull-timePosted 5d ago

About the role

The Director of Recruiting Operations and Systems will lead the strategy, evolution, and execution of the technology, systems, and operating model that powers hiring across Datadog. Oversees Recruiting Operations, Recruiting Technology, and AI Enablement for the recruiting team, supporting ~200 recruiters, sourcers, and coordinators. Hybrid workplace.

Responsibilities

  • Define and execute the long-term goals and roadmap for how our recruiting tech stack can best support and drive efficiency, including recruiting systems, integrations, AI capabilities, automation, and operational workflows.
  • Lead multidisciplinary teams to move from traditional recruiting operations to an AI-native approach.
  • Apply product management principles to gather user feedback and drive experimentation, tool investments, and workflow improvements.
  • Establish responsible AI governance while driving automation initiatives that improve recruiter productivity, hiring quality, and operational efficiency.
  • Partner with People Analytics to ensure workflows provide data for critical business decisions and train recruiting teams on tool usage.
  • Collaborate with Recruiting, Engineering, IT, Security, Finance, People Technology, and executives to drive platform adoption, continuous improvement, and regulatory compliance in AI-enabled hiring.

Qualifications

  • Significant leadership experience in 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 in ATS configuration, Workday-to-Greenhouse connections and data flows, API issue resolution, integrations, and low-code automation tools (e.g., Workato).
  • Strong analytical and systems-thinking skills with ability to translate data into product priorities and executive decisions.
  • Experience leading managers and individual contributors.
  • Exceptional communication and stakeholder management skills with experience influencing senior leaders across functions.
  • Passion for building scalable systems, high-performing teams, and exceptional user experiences through continuous improvement.

Skills

Required:Recruiting operations leadershipATS configuration and integrationsAPI integration and automationProduct managementData-driven decision makingStakeholder management

Benefits

  • Competitive salary and equity package; may include variable compensation
  • Healthcare, dental, parental planning, and mental health benefits
  • 401(k) plan and match
  • Paid time off
  • Fitness reimbursements
  • Discounted employee stock purchase plan
Last updated Oct 22, 2026. Interested? Apply on the company site.

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