Principal Infrastructure Engineer - Microsoft Systems (Remote)

About the Role

Join Greenvelope as a Principal Infrastructure Engineer, where your expertise will directly support a platform used by millions globally. This remote role allows you to work from anywhere while leading the modernization and operation of our Microsoft-based server infrastructure.

What You'll Do

• Own the architecture, reliability, and security of our Microsoft server infrastructure.
• Design, implement, and maintain high-availability systems, including redundancy, failover, and disaster recovery.
• Lead modernization efforts for Windows Server environments and supporting systems.
• Manage server patching, OS upgrades, lifecycle planning, and maintenance windows.
• Own firewall configuration, network security, access controls, and system hardening.
• Monitor system health, performance, and uptime; proactively address risks before they become incidents.
• Serve as the primary escalation point for infrastructure-related production issues.
• Own backup strategies, restore testing, and business continuity planning.
• Partner with developers to support application hosting, deployments, and performance needs.
• Automate operational tasks using scripting and tooling where appropriate.
• Document architecture, runbooks, and operational best practices.
• Continuously improve security posture, reliability, and operational maturity.

Requirements

• Deep experience administering and designing Microsoft Windows Server environments.
• Proven ownership of production infrastructure with high availability and uptime expectations.
• Strong understanding of networking fundamentals, firewalls, and security best practices.
• Experience planning and executing system upgrades with minimal downtime.
• Comfort being the “last line of defense” during incidents.
• Strong judgment, pragmatism, and a bias toward reliability.
• Excellent communication skills with both technical and non-technical teammates.
• Ability to work independently and set technical direction in a small team.

Nice to Have

• Azure or hybrid cloud environments experience.
• Security audits, incident response, or compliance-related work.
• Email infrastructure and providers experience (SendGrid, Mailgun, SparkPost, or similar).
• Prior experience as a senior or principal-level individual contributor.

What We Offer

• Competitive salary based on experience and impact.
• Comprehensive healthcare coverage (medical, dental, vision).
• 401(k) program with company match.
• Fully remote work environment with flexibility and autonomy.
• Generous paid time off and holidays.
• Small, collaborative team with real influence on technical decisions.