AI-Driven Recruiting Operations Leader

Datadog, Inc.; New York (NY); Hybrid; USD 180,000 - 240,000; Full time

Job summary

Datadog is seeking a Director of Recruiting Operations and Systems to lead strategy, evolution, and execution of the technology, systems, and operating model powering hiring across the company. You will oversee Recruiting Operations, Recruiting Technology, and AI Enablement for a team of about 200 recruiters, sourcers, and coordinators in a hybrid workplace.

You will partner with executives and cross-functional teams to drive platform adoption, governance, and continuous improvement, while

Qualifications

• Significant leadership experience in enterprise-scale recruiting operations or comparable platform organizations.
• Proven ability to manage complex technology or operational transformations with measurable impact.
• Experience with ATS configurations, Workday-to-Greenhouse integrations, and data flows.
• Strong analytical and systems-thinking skills; translate data into priorities and executive decisions.

Responsibilities

• Define and execute long-term goals and roadmaps for recruiting tech stack, AI capabilities, automation, and workflows.
• Lead multidisciplinary teams toward an AI-native recruiting approach.
• Apply product management to gather user feedback and drive investments and improvements.
• Establish governance for AI and drive automation to improve recruiter productivity and hiring quality.
• Collaborate with analytics and stakeholders to provide data for business decisions and training.

Skills

Leadership

Recruiting operations

Product management

Data analytics

Stakeholder management

Vendor management

Tools

Workday

Greenhouse

Workato

Job description

Datadog is seeking a Director of Recruiting Operations and Systems to lead strategy, evolution, and execution of the technology, systems, and operating model powering hiring across the company. You will oversee Recruiting Operations, Recruiting Technology, and AI Enablement for a team of about 200 recruiters, sourcers, and coordinators in a hybrid workplace.

You will partner with executives and cross-functional teams to drive platform adoption, governance, and continuous improvement, while