Director, Recruiting Operations

Datadog • Boston, MA

5d • Hybrid

About The Position

The Director of Recruiting Operations and Systems leads the strategy, evolution, and execution of the technology, systems, and operating model supporting hiring across Datadog. The role oversees Recruiting Operations, Recruiting Technology, and AI Enablement for a recruiting function of approximately 200 recruiters, sourcers, and coordinators. It calls for expertise in recruiting, systems, and data, along with a product management mindset, to improve experiences for candidates, recruiting teams, and interviewers.

Datadog operates as a hybrid workplace and values the collaboration and creativity fostered by its office culture. The Director will guide a transformation toward a more progressive, AI-native recruiting approach, using responsible AI governance, automation, and continuous improvement to support hiring quality, recruiter productivity, and operational efficiency. The role partners across People Analytics, Recruiting, Engineering, IT, Security, Finance, People Technology, and executive leadership, and ensures compliance with applicable global laws and regulations governing AI use in hiring.

Requirements

• 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 awareness of solutions available in the market.
• Deep expertise in areas such as 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, including the ability to translate data into product priorities and executive decisions.
• Ability to identify trends in recruiting data and propose ways the team can provide support.
• Experience leading managers and individual contributors.
• Exceptional communication and stakeholder management skills, including experience influencing senior leaders across multiple functions.
• Passion for building scalable systems, developing high-performing teams, and creating exceptional user experiences through continuous improvement.

Responsibilities

• Define and execute the long-term goals and roadmap for recruiting technology, systems, integrations, AI capabilities, automation, and operational workflows.
• Lead multidisciplinary teams in transforming recruiting operations toward a more progressive, AI-native approach.
• Apply product management principles to gather user feedback and guide experimentation, investments in tools, and workflow improvements.
• Establish responsible AI governance and lead automation initiatives that improve recruiter productivity, hiring quality, and operational efficiency.
• Partner with People Analytics to ensure recruiting-system workflows produce data for business decisions and train recruiting teams to use the tools for stronger hiring partnerships.
• Partner with Recruiting, Engineering, IT, Security, Finance, People Technology, and executive stakeholders to drive platform adoption, continuous improvement, and organizational change.
• Ensure compliance with applicable laws and regulations governing the use of AI in hiring decisions globally.
• Lead and develop a multidisciplinary organization spanning operations, technology, analytics, and AI capabilities.

Benefits

• Lead the strategy for a critical enterprise platform and influence how talent is hired at scale.
• Shape AI-enabled recruiting through innovative technologies, automation, and intelligent workflows.
• Partner with senior business leaders to influence company-wide hiring strategy and operational excellence.
• Build and mentor a multidisciplinary organization spanning operations, technology, analytics, and AI capabilities.
• Drive measurable improvements in hiring quality, recruiter productivity, and platform adoption.
• Join a culture that values experimentation, continuous learning, and customer-centered product thinking.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed