Systems Administrator Tier 2 (MSP), AI-Enabled Service Delivery

Modern IT•La Verne, CA

5d•Hybrid

About The Position

Modern IT is a platform-centric managed services provider that propels businesses into the digital age through strategic partnerships with Microsoft and ConnectWise. We are seeking a Systems Administrator Tier 2 (MSP), AI-Enabled Service Delivery, to join our Remote Operations Center (ROC). This role is crucial for maintaining client trust and ensuring high-quality service delivery. The ROC is where issues are triaged, expectations are managed, and problems are solved. The Systems Administrator Tier 2 is the engineer who owns the majority of mid-level and advanced reactive tickets, keeps work moving with clear communication, and shows up on-site when a ticket or user request needs hands-on support. We are building a ROC staffed by capable engineers who combine solid technical skills, strong communication, process discipline, and a genuine interest in using AI and automation to deliver a calmer, smarter service.

Requirements

4-6 years of experience in a Level 2 or higher technical support, escalation, or systems administration role within an MSP environment.
Proven ability to own tickets from intake through resolution in a fast-paced, high-volume service environment.
Hands-on experience supporting Microsoft 365 environments, including Exchange, SharePoint, Teams, Entra ID, identity and access issues, and endpoint troubleshooting.
Strong networking skills, including hands-on troubleshooting across TCP/IP, DNS, DHCP, VPNs, wireless, switching, routing, firewalls, and advanced LAN/WAN connectivity issues.
Hands-on experience in ConnectWise PSA or a comparable PSA/RMM environment, with strong ticket hygiene, documentation, time entry, and workflow discipline.
Ability to communicate technical issues clearly with non-technical clients during urgent or ambiguous incidents, including setting expectations and explaining business impact in clear, non-technical terms.
Proven ability to assess incident severity, business impact, and urgency to ensure issues are prioritized, communicated, and resolved appropriately.
Ability to exercise escalation judgment, knowing when to continue troubleshooting independently and when to engage additional resources with clear, actionable context.
Ability to travel to client sites in the greater Los Angeles area as required, with a valid driver’s license and reliable transportation.
Curiosity and practical interest in using AI, automation, and modern tools to improve service delivery and documentation.
Ownership: Takes responsibility for outcomes, not just assigned tasks.
Calm execution: Brings clarity, structure, and confidence to urgent or ambiguous situations.
Technical curiosity: Enjoys learning, troubleshooting deeply, and understanding why problems happen.
Communication: Knows that great service requires clear expectations, not just technical answers.
Continuous improvement: Looks for patterns, reduces repeat issues, and leaves the system better than found.
People-first service: Cares about the person and business impact behind every technical issue.

Nice To Haves

Microsoft platform: Microsoft 365 Administrator Expert (MS-102), Endpoint Administrator Associate (MD-102), Azure Administrator Associate (AZ-104), Identity and Access Administrator (SC-300)
AI and automation: Azure AI Fundamentals (AI-900), Microsoft Applied Skills related to Copilot and Power Automate
Networking: CompTIA Network+, Cisco CCNA, UniFi/Ubiquiti Academy, Cisco Meraki
Service operations: ConnectWise University, ConnectWise PSA certification, or equivalent hands-on ConnectWise service operations experience.
ITIL 4 Foundation

Responsibilities

Own mid-level and advanced escalated reactive support tickets from intake through resolution, with clear triage, prioritization, communication, documentation, and follow-through.
Provide advanced troubleshooting and support across Microsoft 365, Entra ID, Exchange Online, SharePoint, Teams, Intune, endpoint management, networking, firewalls, VPNs, identity and access management, and client line-of-business applications.
Go on-site to client locations as required for tickets, including hardware, networking, and hands-on support that cannot be resolved remotely.
Communicate with clients during incidents by clearly setting expectations, providing proactive updates, and maintaining confidence through resolution.
Escalate effectively to Senior ROC Engineers or the Service Manager when tickets are stuck, with clear context on what has been tried and what is needed.
Maintain high-quality PSA data in ConnectWise, including notes, time entries, categorization, statuses, resolution details, and next steps.
Maintain and enhance knowledge base articles, troubleshooting guides, and client-specific documentation to improve support quality and operational efficiency.
Identify and communicate recurring issues, trends, and automation opportunities to ROC leadership to support root cause analysis and long-term service improvements.
Adhere to ROC processes, workflows, and operational standards, and actively participate in team meetings, huddles, and scheduled on-call responsibilities.
Actively use AI as part of daily service delivery, including using AI tools to improve ticket analysis, summarize technical work, strengthen documentation, and find answers faster through knowledge retrieval.
Provide real feedback to AI architects and service leaders on what works, what does not, and where automation can remove repetitive work from the queue.
Lead the technical resolution of P1 incidents, including root cause identification.
Contribute to the resolution of P1 incidents, maintaining ownership of assigned workstreams and supporting root cause analysis led by senior engineers.

Benefits

Medical insurance (HMO, PPO, Nationwide, and High-Deductible Plan options)
Coverage effective Day 1
Modern IT contributes toward employee and dependent premiums
Basic Life and AD&D insurance
Optional supplemental Life and AD&D insurance (employee, spouse/domestic partner, children)
Long-Term Disability insurance (employer-sponsored; effective after 3 months)
Optional Dental and Vision insurance (effective Day 1 if elected)
Medical Flexible Spending Account (FSA)
Health Savings Account (HSA) for HDHP participants
Health Advocacy Program (24/7 support for claims, billing, scheduling, coordination)
Employee Assistance Program (confidential counseling and resources)
Additional Voluntary Benefits: Critical Illness, Accident, and Disability coverage
Perks at Work (discounts on travel, electronics, home goods, etc.)
Adoption Assistance Program (up to $1,500 reimbursement)
Commuter Benefits Program (pre-tax transit/parking)
80 hours of PTO per anniversary year (for new full-time employees)
6 paid sick days per anniversary year
7 paid company holidays
Up to 2 floating holidays per calendar year
401(k) plan with employer match