Role Overview

Join Datadog's Enterprise IT Operations - Endpoint team as a Senior Endpoint Administrator in Boston, Massachusetts. This critical role manages thousands of devices across Windows, Linux, and AWS Workspaces environments while ensuring FedRAMP, IL5, and NIST 800-53 compliance. You'll leverage Datadog monitoring and Infrastructure as Code (Terraform, GitOps) to deliver secure, observable endpoints for our cloud-native observability platform serving Fortune 500 customers worldwide.

Datadog's hybrid workplace fosters collaboration while supporting work-life harmony. As endpoint security and compliance become mission-critical for cloud applications, your expertise in endpoint management, cloud security, and DevOps practices will directly impact our ability to serve U.S. government and public sector clients with elevated security rigor.

Key Responsibilities at Datadog

• Operate endpoint tooling supporting FedRAMP, IL5 compliance frameworks with continuous monitoring via Datadog.
• Design and deploy AWS Workspaces Applications environments using Terraform Infrastructure as Code for scalable, auditable deployments.
• Manage Windows and Linux endpoints including patching, hardening, configuration drift detection, and full lifecycle management.
• Implement NIST 800-53 security baselines and validate compliance through automated testing and Datadog dashboards.
• Maintain Git-based workflows for endpoint policies ensuring version control, peer review, and audit trails.
• Partner with Security and Compliance teams for audits, assessments, and real-time threat observability.
• Automate reliability improvements across MDMs and device fleets using DevOps automation and Datadog insights.
• Serve as technical authority for Federal endpoint programs and participate in IT On-Call rotation.
• Drive operational excellence through documentation, automation, and cloud observability best practices.

Qualifications & Requirements

• 7+ years in endpoint administration, enterprise IT operations, or infrastructure engineering roles.
• Proven experience with FedRAMP, IL5, or U.S. Federal compliance frameworks in regulated environments.
• Expertise in Infrastructure as Code using Terraform, CloudFormation, or equivalent for endpoint infrastructure.
• Deep knowledge of Windows and Linux endpoint management, MDM platforms, and security hardening.
• Hands-on experience implementing NIST 800-53 controls and supporting compliance audits.
• Familiarity with AWS Workspaces, GitOps workflows, and modern DevOps tooling.
• Strong collaboration skills working with Security, Compliance, and engineering teams.
• Experience with Datadog monitoring, observability platforms, or similar cloud-native tools is highly desirable.

Salary & Benefits

The estimated salary range for this Senior Endpoint Administrator role at Datadog in Boston is $165,000 - $225,000 USD annually, plus competitive equity, comprehensive benefits, and performance bonuses. Actual compensation depends on experience, skills, and qualifications.

• Competitive equity package with meaningful stock options vesting over 4 years.
• Comprehensive health insurance for individuals and families including dental and vision.
• Generous commuter benefits and public transportation reimbursements.
• Fitness reimbursements up to $100/month for gym memberships and wellness programs.
• Professional development stipend for certifications (AWS, Terraform, FedRAMP) and industry conferences.
• Unlimited PTO and flexible hybrid work supporting Boston office collaboration.
• 401(k) matching and retirement planning support.
• Parental leave and family-friendly benefits including fertility support.

Why Join Datadog?

Datadog is the essential monitoring and security platform for cloud applications, trusted by 20,000+ organizations including Airbnb, Peloton, and Slack. As a Senior Endpoint Administrator, you'll work on mission-critical infrastructure supporting our FedRAMP-authorized environments while leveraging cutting-edge Datadog observability to monitor your own endpoints.

Our Boston team contributes to global IT operations serving customers who rely on Datadog for cloud monitoring, application performance monitoring (APM), log management, and cloud security. Enjoy collaborative office culture, career growth opportunities, and the impact of building secure infrastructure at internet scale.

How to Apply

Ready to secure endpoints at the world's leading observability platform? Apply now for the Senior Endpoint Administrator position in Boston. Submit your resume highlighting FedRAMP experience, Terraform expertise, and endpoint security achievements. Datadog is an Equal Opportunity Employer committed to diversity. We review applications on a rolling basis - don't wait!

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