Help Desk Technician - Gillette, WY

The Help Desk Technician serves as a first point of contact for client support requests involving workstations, Microsoft 365, Windows, basic networking, user accounts, printers, security tools, and common business applications. The successful candidate will troubleshoot issues, communicate updates, escalate when appropriate, and maintain accurate documentation in our ticketing system., · Provide friendly, professional technical support by phone, email, chat, remote session, and in person.

· Troubleshoot and resolve common issues with Windows, Microsoft 365, Outlook, Teams, SharePoint, OneDrive, printers, basic networking, and end-user devices.

· Create, update, and resolve support tickets with clear notes, accurate time entries, and documented next steps.

· Follow established processes for ticket prioritization, escalation, client communication, and service delivery.

· Assist with workstation setup, user account support, password resets, application installs, updates, and basic device configuration.

· Educate clients in a clear, patient, and respectful manner so they understand the resolution and how to avoid repeat issues when appropriate.

· Identify tickets that require escalation and coordinate with higher-level technicians to ensure timely resolution.

· Participate in onboarding, training, knowledge sharing, and continuous improvement efforts.

High school diploma or equivalent required; coursework, training, or certification in information technology is preferred.

Familiarity with Windows computers, Microsoft 365 applications, common mobile devices, basic networking concepts, and general troubleshooting practices.

Strong problem-solving skills with the ability to listen carefully, ask good questions, research solutions, and follow through to resolution.

Excellent verbal and written communication skills, including the ability to explain technical information to non-technical users.

Customer service mindset with patience, professionalism, and a desire to help others succeed.

Ability to manage multiple support requests, follow procedures, prioritize work, and maintain accurate documentation.

Dependable, adaptable, and comfortable working in a team-oriented technical support environment.

Preferred Qualifications

· Previous experience in a help desk, technical support, customer service, or managed IT services role.

· Experience with remote support tools, ticketing systems, and documentation platforms such as ConnectWise, ScreenConnect, or similar tools.

· Entry-level certifications such as CompTIA A+, Network+, Microsoft Fundamentals, or similar credentials.

· Basic understanding of cybersecurity best practices, multi-factor authentication, endpoint protection, and password management.

Pulled from the full job description

• Health insurance
• 401(k) matching
• Paid time off
• Vision insurance
• Dental insurance
• Life insurance, Schedule: Full-time position. Occasional evenings, weekends, or on-call participation may be required based on client and business needs.

Equipment: Company-provided equipment and access to the tools, documentation, and systems needed to perform the role.

Support: Structured onboarding, mentorship from experienced technicians, and opportunities to build technical and client service skills.

Growth Opportunities

· Career advancement into Level 2/3 support or specialized roles (e.g., Systems Administrator, Network Technician, Microsoft 365 Specialist).

· Access to professional certifications and continued education, including Microsoft Certified: Fundamentals and Associate pathways.

· Participation in internal knowledge-sharing sessions and collaborative projects.

Why Join CleverPath IT?

· Join a growing technology company that values teamwork, accountability, and professional development.

· Gain hands-on experience supporting real business clients across a wide range of technologies.

· Work with Microsoft 365, Windows, security tools, remote support platforms, and business technology systems.

· Develop a career path in technical support, systems administration, networking, cybersecurity, or cloud services.

Receive competitive compensation and a benefits package that supports your health and long-term success.

Job Type: Full-time

Pay: $18.00 - $25.00 per hour, * 401(k) matching

• Dental insurance
• Health insurance
• Life insurance
• Paid time off
• Vision insurance

CleverPath IT is seeking a motivated, customer-focused Help Desk Technician to join our team in Gillette, Wyoming. This role is ideal for someone who enjoys solving technical problems, communicating clearly with clients, and learning in a fast-paced managed IT services environment. As a frontline member of our support team, you will help clients resolve technology issues, document work accurately, and deliver a professional support experience that reflects CleverPath IT’s commitment to reliable service and practical solutions.

About CleverPath IT

CleverPath IT provides managed technology services, support, and security-focused solutions for business clients. Our team values responsiveness, accountability, teamwork, and continuous improvement. We invest in our people, encourage professional growth, and work together to help clients use technology with confidence.