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 the recruiting team. You will be a key player leading a team that supports a recruiting function of approximately 200 recruiters, sourcers, and coordinators. We are undergoing an exciting transformation across our People and Recruiting teams, and we need a leader who can bring expertise in recruiting, systems, and data, along with a product management mindset, to help build the best experience for our candidates, recruiting teams, and interviewers. At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create the work-life harmony that best fits them. At Datadog, we place value in our office culture - the relationships and collaboration it builds and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them.   What You'll Do: * 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.   Who You Are: * 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. You should be able to spot trends in recruiting data and propose ways in which your team can provide support. * Experience leading managers and individual contributors. * Exceptional communication and stakeholder management skills, with experience influencing senior leaders across multiple functions. * Passionate about building scalable systems, developing high-performing teams, and creating exceptional user experiences through continuous improvement. Datadog values people from all walks of life. We know that not everyone will meet all of the above qualifications on day one. That's okay. If you're passionate about technology and want to grow your experience, we encourage you to apply. Benefits and Growth: * Lead the strategy for one of the company's most critical enterprise platforms, directly influencing how talent is hired at scale. * Shape the future of AI-enabled recruiting by introducing innovative technologies, automation, and intelligent workflows. * Partner with senior leaders across the business to influence company-wide hiring strategy and operational excellence. * Build and mentor a multidisciplinary organization spanning operations, technology, analytics, and AI capabilities. * Drive meaningful business impact through measurable improvements in hiring quality, recruiter productivity, and platform adoption. * Join a culture that values experimentation, continuous learning, and customer-centered product thinking. Benefits and Growth listed above may vary based on the country of your employment and the nature of your employment with Datadog.       #LI-Hybrid Datadog offers a competitive salary and equity package, and may include variable compensation. Actual compensation is based on factors such as the candidate's skills, qualifications, and experience. In addition, Datadog offers a wide range of best in class, comprehensive and inclusive employee benefits for this role including healthcare, dental, parental planning, and mental health benefits, a 401(k) plan and match, paid time off, fitness reimbursements, and a discounted employee stock purchase plan. The reasonably estimated yearly salary for this role at Datadog is: $200,000—$245,000 USD ---------------------------------------- About Datadog:  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. ---------------------------------------- Equal Opportunity at Datadog: Datadog is proud to offer equal employment opportunity to everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, and other characteristics protected by law. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. Here are our Candidate Legal Notices for your reference.  Datadog endeavors to make our Careers Page accessible to all users. If you would like to contact us regarding the accessibility of our website or need assistance completing the application process, please complete this form. 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