Director, Recruiting Operations

Datadog • Boston, MA

6d • $155,000 - $206,000 • Hybrid

About The Position

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. The role oversees Recruiting Operations, Recruiting Technology, and AI Enablement for a recruiting function of approximately 200 recruiters, sourcers, and coordinators. The Director will help transform the People and Recruiting teams by combining expertise in recruiting, systems, and data with a product management mindset to improve the experience for candidates, recruiting teams, and interviewers.

Datadog operates as a hybrid workplace and values the relationships, collaboration, and creativity built through its office culture. The position leads the recruiting technology strategy and roadmap, supports an AI-native recruiting approach, and partners across the company to strengthen platform adoption, operational efficiency, and compliant use of AI in hiring. The role offers a competitive salary and equity package, which may include variable compensation. Compensation depends on skills, qualifications, and experience.

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.
• 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 and identify trends in recruiting data.
• 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 transitioning from a traditional recruiting operations approach to a more progressive, AI-native approach.
• Use product management principles to gather user feedback and guide experimentation, tool investments, and workflow improvements.
• Establish responsible AI governance and drive automation initiatives to improve recruiter productivity, hiring quality, and operational efficiency.
• Partner with People Analytics to ensure recruiting-system workflows provide data for business decisions and train recruiting teams to use tools for better hiring partnerships.
• Partner with Recruiting, Engineering, IT, Security, Finance, People Technology, and executive stakeholders to drive platform adoption, continuous improvement, and organizational change.
• Ensure ongoing compliance with applicable laws and regulations governing the use of AI in hiring decisions globally.
• Lead and mentor a multidisciplinary organization spanning operations, technology, analytics, and AI capabilities.

Benefits

• Competitive salary and equity package, potentially including variable compensation.
• Healthcare benefits.
• Dental benefits.
• Parental planning benefits.
• Mental health benefits.
• 401(k) plan and match.
• Paid time off.
• Fitness reimbursements.
• Discounted employee stock purchase plan.

What This Job Offers

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