Senior Systems MSP Engineer, AI-Enabled Service Delivery

Jobtailor; La Verne (CA); On-site; USD 95,000 - 130,000; Full time

Job summary

Jobtailor in La Verne, CA is seeking a Senior IT Support professional to own reactive incidents from intake to resolution, coordinating triage, communication, and documentation while on-site and remotely.

You will lead complex Microsoft 365 environments, networking issues, and client environments, mentor teammates, and drive automation and knowledge-base improvements. A strong PSA/RMM tool experience and ConnectWise usage are essential.

Qualifications

• 6+ years of experience in technical support or similar client-facing IT environment.
• Proven ability to own complex incidents from intake through resolution in a fast-paced service setting.
• Strong hands-on experience with Microsoft 365 environments (Exchange, SharePoint, Teams, Entra ID).
• Solid networking fundamentals (TCP/IP, VLANs, routing, firewalls, VPNs, DNS, DHCP).
• Experience using ConnectWise PSA or similar PSA/RMM tools with good ticket hygiene and documentation.

Responsibilities

• Own reactive support incidents from intake through resolution, ensuring triage, prioritization, communication, and documentation.
• Provide technical leadership for complex issues across Microsoft 365, endpoints, networking, identity, access, and client environments.
• Lead client communication during incidents with proactive updates and clear expectations.
• Identify recurring issues and facilitate documentation, standards, automation, or permanent fixes.
• Create and improve knowledge base articles, ticket notes, and resolution details.
• Maintain high-quality PSA data in ConnectWise, including time entries and categorization.
• Mentor teammates to reinforce process discipline and reduce escalations.
• Collaborate with AI architects to turn service patterns into automation and prevention improvements.

Skills

Incident Management

Microsoft 365 Support

Client Communication

Documentation

Mentoring

Process Improvement

Problem-Solving

AI & Automation

Tools

ConnectWise PSA

PSA/RMM Tools

AI Automation Tools

Job description

• 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.

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.

Core Competencies

Demonstrates expertise in managing complex technical support incidents, particularly within Microsoft 365 environments, while maintaining high standards of documentation and client communication. Proficient in identifying service patterns and implementing automation and process improvements to enhance service delivery.

Highest-signal resume keywords

• Microsoft 365 Support
• Incident Management
• ConnectWise PSA Experience
• Networking Fundamentals
• Documentation Discipline

ATS Optimization Keywords

Hard Skills

• Technical Support
• Incident Resolution
• Microsoft Exchange
• SharePoint
• Microsoft Teams
• Entra ID
• TCP/IP
• VLANs
• Routing
• Firewall Troubleshooting

Soft Skills

• Client Communication
• Mentoring
• Process Improvement
• Curiosity
• Problem-Solving

Industry Keywords

• Managed Services
• Client-Facing IT
• Service Patterns
• Root Cause Analysis
• Knowledge Base Management

Tools & Technologies

• ConnectWise
• PSA/RMM Tools
• AI Automation Tools