Responsibilities Deploy Datadog Agent on servers (SQL, IIS web, app), scaling to 350 servers, ensuring comprehensive monitoring of Windows services and performance metrics. Configure Datadog dashboards for real-time visibility into server health, FactorSoft API performance, and infrastructure metrics. Set up monitoring to meet security team requirements for FactorSoft API release, including Windows Event Logs and Cloud SIEM. Automate agent deployment and configuration using tools like Ansible or monitoring-as-code. Develop and deliver training for the DevOps team on Datadog usage, alerting, and dashboard management; provide detailed documentation. Plan for scalability to 500-600 additional servers for other products. Collaborate with stakeholders to align on server counts and project timelines. Optimize Datadog usage costs using Cloud Cost Management features. Qualifications, 5+ years in observability/DevOps; 3+ years with Datadog in Windows environments (IIS, SQL Server, app servers). Expertise in Datadog Agent setup, Windows Service monitoring, and integrations (e.g., SQL Server, Active Directory). Experience with automation (e.g., Terraform, Ansible) and creating dashboards, alerts, and SLOs. Strong communication skills for training and documentation. Datadog certifications (e.g., Fundamentals) or willingness to obtain. Preferred: Experience in financial services, on-premise monitoring, or Datadog security features. Bachelor’s degree in Computer Science or equivalent experience.