Greenvelope.com · 3 hours ago
Principal Infrastructure Engineer (Microsoft Systems)
United States
Full-time
Remote
Lead/Staff
$150K/yr - $200K/yr
8+ years expGreenvelope.com is a company focused on creating beautiful digital invitations and is seeking a Principal Infrastructure Engineer to modernize and operate their Microsoft-based server infrastructure. This senior, hands-on role involves ensuring system reliability, availability, and security while leading major upgrades and serving as the primary decision-maker for infrastructure architecture.
Event ManagementInformation Technology
Responsibilities
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
Qualification
Required
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
Microsoft Windows Server (architecture, administration, and modernization)
Active Directory, Group Policy, DNS, DHCP
High availability and disaster recovery concepts (clustering, failover, redundancy, backups)
Firewall management, network segmentation, and access control
Monitoring, alerting, and logging systems
Microsoft SQL Server (operational awareness, backups, performance support)
PowerShell or similar scripting for automation
IIS and ASP.NET application hosting
Git-based workflows and CI/CD awareness (supporting deployments)
A four-year degree in Computer Science (or equivalent experience such as 8+ years in systems administration or infrastructure roles)
Preferred
Azure or hybrid cloud environments
Security audits, incident response, or compliance-related work
Email infrastructure and providers (SendGrid, Mailgun, SparkPost, or similar)
Experience supporting small engineering teams with production systems
Prior experience as a senior or principal-level individual contributor
Benefits
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
No additional incentive compensation is offered
Company
Greenvelope.com
Uniting beautiful design & streamlined event management tools // elegant, effortless, and eco-friendly digital missives for every occasion
11-50 employees
Funding
Current Stage
Early StageLeadership Team
Sam Franklin
CEO / Founder
Kyle Leesman
Chief Technology Officer
Company data provided by crunchbase