Sr Systems Engineer, AI-Enabled Service Delivery (MSP - Hybrid)
About The Position
This role exists to challenge the traditional MSP model and redefine what great frontline IT service can be. Externally, this role is best understood as a Senior MSP Systems Engineer. Internally, it sits within Modern IT’s ROC, or Reactive Operations Center, where client trust is won or lost. 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. 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 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. 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 proper 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.
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 (up to $50,000 provided by Modern IT)
- 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
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
