Senior Systems Administrator

Job Description:

GreyOwl is hiring a Senior Systems Administrator to serve as the technical escalation point for complex issues across our managed clients. You’ll troubleshoot and resolve high-impact incidents, lead root-cause analysis, mentor Tier 1–2 technicians, and help improve standards, documentation, and tooling. You’ll also partner with projects and leadership to reduce repeat issues and strengthen client environments.

Perks & Benefits:

LA & Seattle:

When you feel good, you do good. At Onni we put your health at the forefront and give you the choice to select a benefits package that best represents you. From no cost to  $11, $44, or $103 per pay our PPO, HSA and HMO have you covered.  In addition we offer:

• 3 weeks PTO

• Annual education allowance of up to $1,000

• Referral program

• Residential housing discount after 1 year of continuous employment

• Friends and family rates for our Hotel Properties throughout the company

Chicago:

• Competitive pay  

• Health Saving Account, Flexible Saving Account, Employee Assistance Program 

• Annual Education Allowance 

• Generous Referral Program 

• Fun and collaborative company culture with lots of team-building events 

• Discounted hotel stays in multiple locations through our Hospitality brand. 

What You Will Do:

Tier 3 Escalation & Incident Resolution

• Take ownership of escalations from Tier 1–2 and drive issues to resolution with strong client communication.

• Troubleshoot complex problems across servers, identity, cloud services, networking, security, endpoints, and line-of-business applications.

• Perform structured root-cause analysis and implement permanent fixes (not just workarounds).

Systems Administration & Platform Ownership

• Administer and improve client environments (typical MSP scope): Microsoft 365, identity, endpoint management, servers/virtualization, backups, and core networking.

• Implement proactive maintenance, monitoring improvements, and security hardening aligned to best practices.

• Support lifecycle initiatives: patching, renewals, onboarding/offboarding, migrations, and standardization.

Service Excellence & Continuous Improvement

• Maintain excellent ticket hygiene: clear notes, time entries, documentation, and closure summaries in the PSA.

• Create and maintain internal KB articles, SOPs, and runbooks.

• Identify recurring pain points and propose/execute automation or process improvements.

• Participate in (or lead) problem management to reduce repeat ticket volume.

Mentorship & Collaboration

• Coach and mentor technicians (technical skills, troubleshooting approach, documentation quality).

• Collaborate with Service Manager/dispatch to prioritize effectively during high-volume periods.

• Partner with Professional Services/Projects for clean handoffs and production-ready implementations.

On-Call / After-Hours (as applicable)

• Participate in an after-hours escalation rotation and support critical incidents when needed.

What You Will Bring:

• 5+ years in IT support, with significant time in Tier 3 / escalation or Senior SysAdmin responsibilities (MSP experience strongly preferred).

• Strong troubleshooting skills across Microsoft-centric environments:

  • Windows Server administration, Active Directory / Entra ID concepts

  • Microsoft 365 administration (Exchange Online, SharePoint/Teams fundamentals)

• Solid networking fundamentals (TCP/IP, DNS/DHCP, VPN, VLANs, firewall concepts).

• Experience with virtualization (VMware or Hyper-V) and backup/DR concepts.

• Scripting/automation mindset (PowerShell preferred).

• Strong written communication and client-facing professionalism.

Salary Range:

$100,000 - $120,000 Per Year

About The Company:

Onni

For over half a century, Onni has been building communities for people to live, work, and play. Our success reflects our commitment to our employees and partners, and our dedication to quality construction, innovation, sustainability, and customer satisfaction. Our expertise expands across North America, with offices in Vancouver, Toronto, Los Angeles, Seattle, Phoenix, and Chicago.

How To Apply:

Please apply through the link on the job posting and attach your resume and any other required documents.

We thank all applicants for your interest in the Onni Group. Note that only those applicants under consideration will be contacted.