The posting
Milestone Retirement · Information Technology
Cloud Systems Administrator (Tier 3)
Hybrid · Full-Time · Reports to the Chief Technology Officer
$90,000 per year
Full-time, salaried base pay
At a glance
- Salary: $90,000 per year
- Schedule: Full-Time · Salaried · Exempt
- Work arrangement: Hybrid, in-office and remote, with travel to communities and corporate offices as needed
- Department: Information Technology
- Reports to: Chief Technology Officer (CTO)
Why you’ll want this role
Technology at Milestone keeps senior living communities running around the clock, and this role is where the hardest problems land. As our Tier 3 Cloud Systems Administrator, you’ll own the cloud, identity, network, and SaaS environments that support our residents and team members in Oklahoma, California, Washington, Colorado, and Oregon.
You’ll have room to build: design new on-premises and cloud systems to industry standards, write the automation that keeps them consistent, and set the configuration standards the rest of the IT team follows. Your work has a direct line to resident care.
What you’ll do
Run and protect our systems
- Administer, configure, audit, and maintain the systems that support daily operations at every community and our Support Center, including identity, access, device management, and file services.
- Administer Microsoft 365 and Google Workspace (users, devices, groups, conditional access, security policies) and support enterprise SaaS platforms such as Yardi.
- Support community and Support Center networks, including firewalls, VLANs, switching, and Wi-Fi, and work with internet and network vendors on installs, outages, and upgrades.
- Apply patches, updates, and security baselines on a regular schedule, following change control.
Be the final escalation point
- Oversee Tier 3 escalations from the help desk, making sure issues are prioritized, resolved, and documented.
- Assess incidents quickly for business impact and urgency, find the root cause, and keep users and leaders informed until service is restored.
- Lead root-cause reviews after significant outages.
Prevent problems before they start
- Watch systems, endpoints, and ticket trends to catch issues before they become outages.
- Put permanent fixes in place through patches, configuration changes, and automation.
- Build knowledge-base articles, SOPs, and self-service resources that reduce ticket volume.
Design and build what’s next
- Design and implement new on-premises and cloud systems that meet best practices for security, reliability, and scalability.
- Plan and lead technical projects from requirements through testing, rollout, and handoff.
- Find and drive improvements to workflows for IT and for community operations.
Keep us secure and compliant
- Safeguard ePHI and sensitive data in line with HIPAA, the HITECH Act, and Milestone security policy.
- Apply practices aligned with the NIST Cybersecurity Framework and HHS 405(d) HICP: least privilege, multifactor authentication, encryption, logging, and timely account provisioning and deprovisioning.
- Support audits and security reviews, keep documentation audit-ready, and respond to security incidents according to our procedures.
Document, communicate, and mentor
- Maintain the authoritative documentation for our infrastructure, including network maps, system configurations, and change records.
- Explain technical issues, risks, and options clearly to non-technical staff and leaders.
- Coach help desk and Tier 2 staff through documentation, training, and hands-on support, and lead project teams as assigned.
How we work
- Compassion. We lead with empathy, respond patiently, and communicate clearly with non-technical staff, remembering that reliable technology supports resident care.
- Innovation. We look for better ways to solve and prevent problems, automate repetitive work, and champion tools that scale as Milestone grows.
- Accountability. We document our changes, follow change control, close the loop with users, and report results openly and on time, including outages and mistakes.
What you bring
Required
- Associate’s or Bachelor’s degree in Information Technology, Computer Science, Information Systems, or a related field, or an equivalent combination of education, certification, and directly relevant experience.
- Cloud services administration experience with Microsoft 365, AWS, or Google Workspace.
- Working knowledge of identity and access management, multifactor authentication, and endpoint security tools.
- Understanding of ITIL concepts (incident, problem, and change management) and experience with ticketing systems and service levels.
- Strong problem-solving, analytical, and communication skills, and the discretion to handle sensitive information confidentially.
- Ability to work a hybrid schedule with on-site travel as needed, including occasional overnight travel.
Nice to have
- Enterprise SaaS administration experience, particularly Yardi.
- Experience managing networks and domain environments and producing infrastructure documentation and diagrams.
- Scripting in PowerShell, Python, or Bash.
- Familiarity with HIPAA, the HITECH Act, the NIST Cybersecurity Framework, HHS 405(d) HICP, and handling ePHI.
- Experience managing a team.
Work environment
- Hybrid role; both in office and remote, must be reachable during scheduled support hours, with flexibility to support communities in the Pacific, Mountain, and Central time zones.
- Travel to communities and corporate offices, including occasional overnight travel.
- After-hours or on-call support may be needed during incidents, outages, or scheduled maintenance.
- Ability to lift and handle IT equipment, typically up to 25–50 lbs, during on-site deployments.
Ready to make technology work for the people who make Milestone home? Apply today.
All duties listed are essential job functions and may be modified to reasonably accommodate individuals with disabilities. This description is not an employment agreement and may change as business needs change.
