DataDog Observability Engineer - Part Time (R-00231)

True Zero Technologies, a veteran-owned small business, was founded on the principle that the purposeful enablement of people and technology in an organization directly ties to the quality of its outcomes. True Zero recognizes that those outcomes begin and end with our people, and that is what we have built a community of like-minded, driven, and passionate individuals and innovators who are aligned in a common goal of delivering top-tier services to our customers. Our culture and commitment have been recognized through numerous accolades, including being named one of the Best Places to Work in 2023 in two categories (“Prosperous and Thriving” ($5MM–$50MM in gross revenue) and “Mid-Atlantic Region” (DC, DE, MD, NC, VA, WV)), and again in 2025 as a Best Places to Work honoree. In addition, True Zero earned coveted spots on the Inc. 5000 list of fastest-growing companies in America in 2022, 2023, and 2025 , a testament to our sustained growth driven by our people-first approach and unwavering dedication to excellence. Position Overview True Zero is seeking a Datadog Observability Engineer to lead the design, implementation, and operation of enterprise-grade observability solutions built on the Datadog platform across secure, mission-critical, and healthcare environments. This is a senior technical role for an engineer who pairs deep, hands-on expertise in infrastructure monitoring, APM, log management, and synthetic testing with the judgment to guide teams, engage clients, and deliver production-grade, highly reliable observability capabilities. The ideal candidate brings a track record of architecting and operating Datadog environments across large, distributed systems — including experience monitoring healthcare applications and infrastructure subject to HIPAA and other regulatory requirements, where uptime, data integrity, and patient-safety-critical alerting are paramount. Experience integrating endpoint and asset visibility from Tanium into the overall observability and security architecture is a strong plus, giving teams a unified view across infrastructure health, application performance, and endpoint risk. Job Responsibilities Observability Architecture: Design, implement, and maintain end-to-end observability solutions using Datadog — infrastructure monitoring, APM/distributed tracing, log management, RUM, and synthetic monitoring — across cloud and on-premises environments. Dashboard & Alerting Development: Build and maintain dashboards, SLOs, and intelligent alerting policies that surface actionable signal and reduce noise for on-call teams. Healthcare Systems Monitoring: Implement and tune observability for healthcare applications and infrastructure (EHR/EMR platforms, HL7/FHIR interfaces, clinical systems) to protect uptime, data integrity, and compliance with HIPAA and related regulatory requirements. Log & Metrics Pipeline Engineering: Configure log pipelines, custom metrics, and telemetry ingestion (via Datadog Agent, OpenTelemetry, and APIs) to ensure high-fidelity, cost-efficient data collection at scale. Incident Response & On-Call Support: Partner with SRE and engineering teams to detect, triage, and resolve incidents; drive root-cause analysis and post-incident reviews using Datadog’s tooling. Systems & Security Integration: Integrate the Datadog platform with existing ITSM, CI/CD, and security tooling; collaborate with security teams to incorporate endpoint and asset data from Tanium into the overall observability and security architecture for unified risk and health visibility. Infrastructure as Code: Manage Datadog configuration (monitors, dashboards, SLOs) as code using Terraform or the Datadog API/CLI to ensure consistency, version control, and repeatable deployments. Cost & Performance Optimization: Monitor and optimize Datadog usage, tagging strategy, and data retention to control cost while maintaining coverage and performance. Governance & Compliance: Ensure observability practices align with regulatory and security requirements, including HIPAA, NIST SP 800-53, and Zero Trust principles. Reporting: Deliver technical reports on system health, performance trends, and reliability posture with clear, actionable recommendations. Client Collaboration: Engage with clients and stakeholders throughout the project lifecycle to align observability strategy with mission and business objectives. Team Development: Coach and mentor junior engineers on observability best practices and Datadog platform capabilities. Job Qualifications Experience: Minimum of 5 years in observability, DevOps, SRE, or systems engineering, with substantial hands-on experience administering and architecting the Datadog platform. Citizenship: U.S. citizenship required; must be willing to undergo a U.S. Government background investigation. Datadog Expertise: Deep hands-on experience with Datadog APM, Infrastructure Monitoring, Log Management, Synthetic Monitoring, RUM, and Cloud Security Management. Healthcare Experience: Experience monitoring and supporting healthcare applications and infrastructure (EHR/EMR, HL7/FHIR, clinical or patient-facing systems) in HIPAA-regulated environments is highly valued. Endpoint & Security Integration: Familiarity with Tanium or similar endpoint management/visibility platforms, and experience incorporating endpoint telemetry into the overall observability and security architecture, is a strong plus. Cloud & Infrastructure: Hands-on experience with major cloud platforms (AWS, Azure, GCP), containerized environments (Kubernetes, Docker), and hybrid/on-prem infrastructure. Automation & IaC: Proficiency with Terraform and scripting/automation (Python, Bash) for configuration-as-code and pipeline automation. Methodologies: Strong understanding of SRE principles, SLIs/SLOs/error budgets, incident management, and root-cause analysis. Governance: Familiarity with NIST SP 800-53, HIPAA technical safeguards, and Zero Trust architecture principles. Integration: Experience integrating observability tooling with ITSM platforms (ServiceNow, Jira), CI/CD pipelines, and SIEM/security tooling. Communication: Excellent written and verbal skills to convey technical information to diverse audiences. Education: Bachelor’s degree in Computer Science, Information Technology, Engineering, or a related field preferred; equivalent experience considered. Certifications Candidates should possess three or more of the following: Datadog Fundamentals Certification Datadog APM & Distributed Tracing Fundamentals Certification Datadog Log Management Fundamentals Certification AWS Certified Solutions Architect – Associate or AWS Certified DevOps Engineer – Professional Microsoft Certified: Azure Administrator Associate or Azure Solutions Architect Expert Google Cloud Professional Cloud DevOps Engineer Certified Kubernetes Administrator (CKA) HashiCorp Certified: Terraform Associate ITIL Foundation Certification We’re actively searching for talented and expereinced professionals who are ready to experience the True Zero difference. As a True Zero team member, you’ll enjoy: