Join a nimble, product-focused team where your work directly supports a platform used by millions of people worldwide. Greenvelope was founded in Seattle in 2008 with a simple idea: create beautiful, effortless, environmentally friendly digital invitations. Sixteen years later, we’re still crafting thoughtful experiences for hosts and guests all over the world.

We’re a small, tight-knit team of fewer than 20 people, and we like it that way. Our size means less red tape, more autonomy, and real ownership. Several team members have celebrated 10+ year anniversaries, and we’re intentional about maintaining a culture where smart, kind people enjoy working together long-term.

If you enjoy being the technical authority for infrastructure, designing systems that are calm under pressure, and owning availability and security end-to-end, this role could be a great fit.

Summary

We’re looking for a Principal Infrastructure Engineer to own, modernize, and operate Greenvelope’s Microsoft-based server infrastructure. This is a senior, hands-on individual contributor role with full responsibility for system reliability, availability, security, and ongoing improvements.

You’ll act as the primary decision-maker for infrastructure architecture, lead major upgrades and improvements, and serve as the escalation point for production issues. While you’ll work closely with our development team, this role is not focused on feature development. It is focused on keeping systems stable, secure, and resilient.

Although Greenvelope is proudly rooted in Seattle, this is a fully remote role.

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

What we’re looking for

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

Core tools and experience

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)

Bonus experience

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

You are

Calm and methodical under pressure
Thoughtful about risk and tradeoffs
Highly accountable for systems you own
Pragmatic and solutions-oriented
Comfortable making decisions with imperfect information

Benefits

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
No additional incentive compensation is offered

Experience:

A four-year degree in Computer Science (or equivalent experience such as 8+ years in systems administration or infrastructure roles).

Employment Type: Full time / W-2

Location: Remote (WA, IL, MO, CA, or OR)

Compensation: $150k-$200k annual base salary depending on experience

To apply: Please answer the following two questions with your application:

Describe a recent (within the last 3–5 years) production Windows Server environment you personally owned or led as the primary technical authority.
Walk through your standard approach to planning and executing a major Windows Server OS upgrade (e.g., 2016 → 2019/2022) or a significant modernization effort in a production environment where high availability and minimal downtime were critical.

Applicants who need a reasonable accommodation for any part of the application or hiring process may contact hr@greenvelope.com. Requests will be considered in accordance with the ADA and applicable state law.

California applicants, please review our Privacy Policy

https://www.greenvelope.com/terms#privacy

Greenvelope is an Equal Opportunity Employer and does not discriminate on the basis of any protected characteristic.

Greenvelope.com jobs

Principal Infrastructure Engineer (Microsoft Systems)

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