Remote Server Administrator Jobs in Portland, OR

Heroic Technologies is a growing Managed IT and Cybersecurity firm serving professional services organizations across the West Coast. 

Despite the name, we believe great outcomes come from strong systems and teamwork, not last-minute rescues. We operate on standards, not heroics. Documentation, accountability, and disciplined execution matter here. 

Our environment rewards engineers who value structure, repeatability, and long-term improvement over ad-hoc fixes. If you prefer long-term system health over firefighting, we’d love to meet you. 
 

The Role 

We are hiring an MSP Jr. Systems Administrator to actively support and help manage client infrastructure environments. In this role, you will take ownership of day-to-day administration across standard Windows server, identity, and network environments, independently resolving routine to moderately complex issues while escalating advanced challenges to senior engineers when needed.
We're looking for someone eager to grow into a full-fledged Systems Administrator role. You'll get hands-on exposure across a broad range of technologies, direct mentorship from senior team members, and a path to full independence as your skills develop

What You’ll Do  

• Manage Windows Server environments (AD, DNS, DHCP, file services) 

• Troubleshoot Group Policy and identity issues 

• Manage firewall and VPN configurations 

• Support VLAN and subnet design within defined standards 

• Lead infrastructure upgrades and migrations 

• Implement secure Microsoft 365 and other cloud configurations 

• Reduce repeat issues through documentation and training 

At Heroic, infrastructure stewardship means ownership. 

• You are accountable for the stability, reliability, and security of assigned client environments. 

• You resolve most infrastructure issues independently and confidently. 

• You operate within defined standards—and contribute to improving them. 

• You document your work so others can execute it without you. 

• You elevate the capability of the team, not just your own skill set. 

Bottom line, you are not just supporting servers, networks and systems. You are responsible for keeping them stable, secure, and aligned to standards. 
 

What We're Looking For

• At least one year of hands-on IT infrastructure experience

• One year of experience in an MSP or IT services environment is required

• Windows Server administration experience 

• Firewall/VPN configuration and administration experience

• Strong networking fundamental knowledge

• Proven troubleshooting methodology 

Preferred Competencies 

• MS-102 (or ability to obtain within 90 days) 

• Network+ 

• Security+ 

HR Information 

• Full Time, permanent position 

• Salary: $70,000-$90,000 

• Medical, Dental, Vision (TriNet) 

• 401(k) with match 

• PTO + Holidays 

• Professional development budget 

• Remote role with some travel as needed - must be located in the West Coast