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. 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.
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 certifications: Microsoft 365 Administrator Expert, Azure Administrator Associate, Endpoint Administrator Associate, Identity and Access Administrator Associate, Security Operations Analyst Associate.
- AI and automation certifications: Azure AI Fundamentals, Power Platform Fundamentals, Microsoft Applied Skills related to Copilot, Power Automate, Azure AI, AI agents, or automation workflows.
- Networking certifications: CCNA, Network+, UniFi/Ubiquiti Academy, Cisco Meraki, or equivalent networking training.
- Service operations certifications: 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 (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)
- 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
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
