IT Support Technician – Tier I AI Integration, Documentation & Knowledge Management Lead

Iserv; Orlando (FL); On-site; USD 32,000 - 52,000; Full time

Job summary

iServ in Orlando, FL seeks an IT Support Technician – Tier I to join our Desktop Support / Managed Services team. This role blends frontline technical support with added focus on AI integration, knowledge management, and cybersecurity awareness.

The successful candidate will contribute to documentation quality, standard operating procedures, and continuous improvement across the service desk while operating in a fast-paced MSP environment.

Qualifications

• Experience with Windows 10/11 and Microsoft 365 applications.
• Solid understanding of basic networking concepts required.
• Ability to document solutions and troubleshooting steps clearly.

Responsibilities

• Provide professional Tier I IT support with emphasis on first-call resolution.
• Troubleshoot Windows 10/11, M365, Outlook, Teams, printers, and network issues.
• Diagnose DNS/DHCP/VPN problems and handle connectivity troubles.
• Manage ConnectWise tickets with accurate notes and timely updates.
• Document recurring issues and create troubleshooting guides.
• Collaborate with Tier II and other teams to resolve issues.
• Support AI-assisted troubleshooting initiatives and automation efforts.
• Maintain security awareness in accordance with best practices.

Skills

Windows troubleshooting

Microsoft 365

Networking basics

Documentation

Customer service

Team collaboration

Education

Degree in IT/CS preferred

CompTIA Security+ or equivalent preferred

Microsoft Azure or cybersecurity certifications an advantage

Tools

ConnectWise

Microsoft Teams

Outlook

Job description

IT Support Technician – Tier I

AI Integration, Documentation & Knowledge Management Lead

Company: iServ

Department: Desktop Support / Managed Services

Schedule: 7:30 AM – 4:00 PM Eastern, with alternating weekend rotation

Reports To: Desktop Support Management

Position Summary

At iServ, we believe exceptional technical support goes beyond answering calls and closing tickets. We are looking for individuals who take ownership, solve problems, share knowledge, and help improve how we deliver service.

The IT Support Technician – Tier I | AI Integration & Knowledge Management Lead combines frontline technical support with additional responsibilities focused on technical documentation, AI-assisted troubleshooting, cybersecurity awareness, and continuous improvement.

This position is designed for someone who demonstrates leadership through initiative, collaboration, accountability, and knowledge sharing rather than supervisory authority.

The successful candidate will serve as a frontline technical resource while helping build a stronger, more consistent, and better-documented Desktop Support operation.

1. Core Tier I Technical Support

• Provide professional technical support to iServ customers, emphasizing first-call resolution.
• Troubleshoot Windows 10/11, Microsoft 365, Outlook, Teams, network connectivity, printers, and common business applications.
• Diagnose basic DNS, DHCP, VPN, wireless, and connectivity issues.
• Manage assigned ConnectWise tickets, ensuring accurate notes, timely customer communication, and proper resolution documentation.
• Work collaboratively with Tier II, Advanced Services, and other technical teams to resolve issues.
• Participate in monitoring, incident response, and scheduled support coverage.
• Assist with occasional onsite technical support and equipment installations.
• Maintain customer satisfaction and follow established service-level expectations.

2. Technical Documentation & Knowledge Management Leadership

• Take the lead in identifying recurring technical issues that require documented solutions.
• Develop and maintain troubleshooting guides, knowledge base articles, and standard operating procedures.
• Work with Tier I, Tier II, and Advanced Services technicians to capture successful troubleshooting methods.
• Convert resolved tickets into reusable documentation when appropriate.
• Help establish consistent documentation standards within ConnectWise and approved knowledge management platforms.
• Review existing documentation and recommend updates when information becomes outdated.
• Encourage technicians to use existing documentation before escalating issues.
• Help identify knowledge gaps contributing to repeat tickets, unnecessary escalations, or extended resolution times.
• Collaborate with team leads and management to improve documentation quality and accessibility.

Leadership Expectation

This role is not a supervisory or management position. Leadership is demonstrated by setting a positive example, sharing knowledge, supporting colleagues, and taking ownership of documentation improvements.

3. AI Integration & Support Automation

• Explore and evaluate approved AI tools that improve technical troubleshooting and customer support.
• Help develop AI-assisted troubleshooting guides and workflows.
• Identify repetitive support tasks that may benefit from scripting or automation.
• Assist management in evaluating AI-generated ticket summaries, documentation, and suggested resolutions.
• Work with the team to improve consistency and efficiency through AI-supported processes.
• Participate in pilot programs involving AI-based service desk tools.
• Ensure AI tools are used responsibly, following company security and customer confidentiality requirements.
• Measure and communicate the effectiveness of approved AI initiatives.

4. Cybersecurity & Operational Awareness

• Apply cybersecurity principles when troubleshooting customer environments.
• Recognize and properly escalations potential security incidents, suspicious activity, and vulnerabilities.
• Support established security procedures involving Microsoft 365, Azure, identity management, and endpoint protection.
• Assist in documenting security-related incidents and resolutions.
• Contribute to process improvements aligned with NIST and other applicable security frameworks.
• Work with senior technical resources on approved security-related initiatives.

5. Team Collaboration & Informal Leadership

• Serve as a positive technical resource for other Tier I technicians.
• Share newly discovered solutions and troubleshooting methods.
• Assist newer team members in locating documentation and following established procedures.
• Identify opportunities to improve service delivery and communicate recommendations to management.
• Help promote accountability, consistent ticket updates, and customer communication.
• Support a team culture built on collaboration, professional development, and continuous improvement.

This position does not include direct employee supervision, disciplinary authority, or formal performance management responsibilities.

6. Qualifications

Required or Preferred Technical Knowledge

• Working knowledge of Windows operating systems, Microsoft 365, and fundamental networking.
• Understanding of troubleshooting methodologies and customer service principles.
• Familiarity with Microsoft Azure and cybersecurity best practices.
• Ability to produce clear, accurate technical documentation.
• Interest in AI technologies, automation, and operational improvements.
• Strong written and verbal communication skills.
• Ability to work independently while collaborating with multiple technical teams.

Education & Certifications

• Degree in Information Technology, Computer Science, Cybersecurity, or related field preferred.
• CompTIA Security+, Network+, or equivalent certifications preferred.
• Microsoft Azure, AI, or cybersecurity certifications are an advantage.
• Hands‑on MSP experience preferred, with consideration given to relevant education, technical projects, and demonstrated troubleshooting ability.

7. Performance Expectations

Success in this position will be measured through both technical support performance and contributions to operational improvements.

• Consistent ticket ownership and timely customer communication.
• Strong first-call resolution performance.
• Accurate and complete ticket documentation.
• Creation and maintenance of useful technical knowledge articles.
• Reduced repeat troubleshooting and avoidable escalations.
• Positive collaboration with Tier I, Tier II, and Advanced Services.
• Meaningful participation in approved AI and automation initiatives.
• Positive customer feedback and adherence to established SLAs.

8. Growth Opportunities

This position provides a development path into areas such as:

• Tier II Technical Support
• Technical Knowledge Management
• AI & Support Automation
• Cybersecurity Operations
• IT Service Management and Process Improvement