Director, Recruiting Operations

Boston · New York · USD 155,000-206,000 / year · Full-time · Hybrid · Posted Oct 16, 2026

At a glance

Datadog is the leading observability and security platform for the AI era, providing businesses with unified visibility across the technology stack to manage complexity at scale. It brings applications, infrastructure, data, models, and security into one place, using AI to detect and resolve issues before they impact customers. Trusted globally by Fortune 500 companies and high-growth AI leaders, Datadog enables businesses to move faster with clarity and confidence. Learn more about #DatadogLife on Instagram, LinkedIn, and Datadog Learning Center.

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.
This leader will oversee Recruiting Operations, Recruiting Technology, and AI Enablement for a recruiting team supporting approximately 200 recruiters, sourcers, and coordinators.
You will bring expertise in recruiting, systems, and data along with a product management mindset to build the best experience for candidates, recruiting teams, and interviewers.

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 us from a traditional recruiting operations approach to a more progressive, AI-native approach.
Apply product management principles to continually gather user feedback and use it to drive experimentation, new tool investments, and workflow improvements.
Establish responsible AI governance while driving automation initiatives that improve recruiter productivity, hiring quality, and operational efficiency.
Partner with our People Analytics teams to ensure that the workflows in our recruiting systems provide the data needed to drive critical business decisions and train recruiting teams on how to use these 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, while ensuring that we continually comply with applicable laws and regulations governing the use of AI in hiring decisions globally.

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, maintaining awareness of the solutions available in the market, and developing 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 with the 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 multiple functions.

We operate as a hybrid workplace to ensure our Datadogs can create the work-life harmony that best fits them.
Datadog places value in office culture, including the relationships and collaboration it builds and the creativity it brings to the table.