Sr Systems MSP Engineer, AI-Enabled Service Delivery (Hybrid)

ModernIT•La Verne, CA

2d•$110,000 - $130,000•Hybrid

About The Position

Modern IT is a new kind of MSP: more intentional, more informed, and more inspired. Founded on the belief that today’s business needs require different, we’ve rewritten the rules of IT against tool sprawl and hardware that creates more headaches than help. Our ideology is simple: IT should put people and business into motion, not stand in the way. By thoughtfully putting services over servers, training and trust over technology, and heartbeats over hardware, we help harmonize people and processes and create IT ecosystems that foster calm, spur confidence, and energize people in the right direction: forward. Modern IT is a platform-centric managed services provider that propels businesses into the digital age through strategic partnerships with Microsoft and ConnectWise. With a global clientele and a distributed team, we are positioned at the forefront of innovation and operational excellence. Why This Role Exists Client trust is built—or lost—every single day inside Modern IT’s Reactive Operations Center. This team sits at the heart of the client experience, owning critical moments that directly impact service quality and long-term relationships. Internally, we refer to this team as the ROC (Remote Operations Center), and this role as ROC L2. Externally, this role is best understood as a Senior MSP Systems Engineer. Internally. At Modern IT, we believe this work deserves senior-level talent. We are building a ROC led by engineers who combine technical depth, business awareness, strong communication, and a passion for improving the way service is delivered. The AI era requires a new kind of service engineer: someone who can troubleshoot deeply, think systematically, mentor others, and work with AI architects to turn real service patterns into automation, prediction, better documentation, and better client outcomes. Who Thrives in This Role This role is for the senior technical leader who has seen enough reactive IT to know there has to be a better way. You may be the person everyone already goes to when tickets get complicated, when clients need clarity, or when the team needs a calm technical leader to help move things forward. You enjoy solving technical problems, but you also care about the human experience behind the issue. You do not want to spend your career closing tickets just to hit a metric. You want to identify patterns, improve systems, mentor teammates, and help build a service model that is smarter, calmer, and more scalable. This role is also for the engineer who wants meaningful access to AI and the opportunity to build with it as part of real service delivery. You will work alongside AI architects and service leaders to identify where automation, ticket intelligence, knowledge retrieval, and predictive support can improve the experience for both clients and engineers. If you are energized by deep technical problem-solving, continuous learning, client trust, and the chance to help reinvent frontline IT for the AI era, this role was built for you. Success Factors Success in this role is measured by the ability to create a calmer, more reliable, and more scalable service experience for clients and engineers. Client Environments Become Quieter and More Stable: Client environments become more stable over time, with the ROC driving toward world-class benchmarks of fewer than 0.25 reactive hours per user per month and fewer than 0.25 tickets per user per month. Issues Are Resolved Quickly and Correctly : More than 80% of eligible reactive incidents are resolved the same day, without sacrificing quality, documentation, communication, or long-term fix discipline. Clients Feel Informed and Confident: Clients do not have to chase updates or wonder who owns their issue. Communication is proactive, clear, expectation-driven, and trust-building throughout the incident lifecycle. Knowledge Compounds Across the ROC: Meaningful resolutions improve documentation, knowledge base quality, and team repeatability, reducing dependency on tribal knowledge and helping the next engineer resolve similar issues faster. AI and Automation Create Real Service Leverage: AI and automation are used to identify patterns, improve documentation, reduce repeat issues, support faster resolution, and help the ROC prevent more problems before they become tickets. What You’ll Own Own reactive support incidents from intake through resolution, ensuring clear triage, prioritization, communication, documentation, and follow-through, both remotely and on-site. Provide technical leadership for complex issues across Microsoft 365, endpoints, networking, identity, access, and client environments, both remotely and on-site. Lead client communication during incidents by setting expectations, providing proactive updates, and maintaining confidence throughout the resolution process. Identify recurring issues, service patterns, and root causes that should become documentation, standards, automation, or permanent fixes. Create and improve knowledge base articles, ticket documentation, troubleshooting guides, and client-specific support notes. Maintain high-quality PSA data in ConnectWise, including notes, time entries, categorization, statuses, resolution details, and next steps. Support ROC team consistency by mentoring teammates, sharing knowledge, reinforcing process discipline, and helping reduce unnecessary escalations. Partner with leadership and AI architects to turn real service patterns into practical AI, automation, documentation, and prevention improvements. AI-Enabled Service Delivery This role is expected to actively use and help shape AI-enabled service delivery. That means using AI to improve ticket analysis, summarize technical work, strengthen documentation, identify recurring patterns, support knowledge retrieval, and surface opportunities for automation. The goal is not to replace great engineering judgment with AI. The goal is to give great engineers better tools, better insight, and more leverage.

Requirements

6+ years of experience in technical support, managed services, or a similar client-facing IT environment.
Proven ability to own complex incidents from intake through resolution in a fast-paced, high-volume service environment.
Strong hands-on experience supporting Microsoft 365 environments, including Exchange, SharePoint, Teams, Entra ID, identity/access issues, endpoint troubleshooting, and tenant-level administration.
Solid networking fundamentals, including TCP/IP, VLANs, routing, firewalls, wireless, VPNs, DNS, DHCP, and WAN/LAN troubleshooting.
Hands-on experience working in ConnectWise PSA or a comparable PSA/RMM environment, with strong ticket hygiene, documentation, time entry, categorization, and workflow discipline.
Ability to communicate clearly with clients during urgent or ambiguous incidents, including setting expectations, explaining impact, and maintaining confidence.
Strong documentation discipline, including clear ticket notes, resolution details, knowledge base contributions, root cause findings, and repeat issue tracking.
Demonstrated ability to identify recurring issues, improve processes, and contribute to standards, automation, or permanent fixes.
Curiosity and practical interest in using AI, automation, and modern tools to improve service delivery, documentation, knowledge retrieval, and issue prevention.

Nice To Haves

Microsoft platform: Microsoft 365 Administrator Expert, Azure Administrator Associate, Endpoint Administrator Associate, Identity and Access Administrator Associate, Security Operations Analyst Associate.
AI and automation: Azure AI Fundamentals, Power Platform Fundamentals, Microsoft Applied Skills related to Copilot, Power Automate, Azure AI, AI agents, or automation workflows.
Networking: CCNA, Network+, UniFi/Ubiquiti Academy, Cisco Meraki, or equivalent networking training.
Service operations: ConnectWise University, ConnectWise PSA certification, or equivalent hands-on ConnectWise service operations experience.

Responsibilities

Own reactive support incidents from intake through resolution, ensuring clear triage, prioritization, communication, documentation, and follow-through, both remotely and on-site.
Provide technical leadership for complex issues across Microsoft 365, endpoints, networking, identity, access, and client environments, both remotely and on-site.
Lead client communication during incidents by setting expectations, providing proactive updates, and maintaining confidence throughout the resolution process.
Identify recurring issues, service patterns, and root causes that should become documentation, standards, automation, or permanent fixes.
Create and improve knowledge base articles, ticket documentation, troubleshooting guides, and client-specific support notes.
Maintain high-quality PSA data in ConnectWise, including notes, time entries, categorization, statuses, resolution details, and next steps.
Support ROC team consistency by mentoring teammates, sharing knowledge, reinforcing process discipline, and helping reduce unnecessary escalations.
Partner with leadership and AI architects to turn real service patterns into practical AI, automation, documentation, and prevention improvements.
Actively use and help shape AI-enabled service delivery, including using AI to improve ticket analysis, summarize technical work, strengthen documentation, identify recurring patterns, support knowledge retrieval, and surface opportunities for automation.

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)
60% of earnings up to $10,000/month
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)
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
Eligibility begins the first day of the month following 3 months of employment