Helper Connectwise Jobs in Iowa (NOW HIRING)

Reports to: Service Operations Manager

As a Help Desk Technician (Tier 1) at Winsor Consulting Group, you will serve as the first point of contact for our clients, providing frontline technical support for a wide range of IT issues. This client-facing role is essential to maintaining positive customer relationships and ensuring the smooth operation of our clients’ environments. You'll work within a team-oriented service desk, triaging and resolving issues or escalating as necessary, while documenting your work accurately and consistently in our systems.

You will contribute to a standardized, ITIL-aligned support experience that reinforces Winsor’s reputation for fast, professional, and reliable service. Success in this role comes from responsiveness, clear communication, a desire to learn, and an ability to follow processes.

• Provide Level 1 support for clientreported issues via phone, email, or ticketing system.
• Troubleshoot common user issues including password resets, email access, device performance, printing, and basic networking.
• Monitor and respond to alerts for supported environments.
• Participate in the oncall rotation to provide afterhours emergency support as scheduled.
• Configure and deploy new workstations per Winsor’s documented imaging and setup procedures.
• Travel onsite when necessary to assist with support issues that require a physical presence.
• Escalate unresolved issues to Tier 2 or Systems teams following Winsor’s documented escalation paths.
• Maintain accurate and thorough documentation of client interactions, troubleshooting steps, and resolutions.
• Adhere to established SLAs, escalation timelines, and clientspecific standards.
• Contribute to internal documentation and process improvement initiatives.
• Deliver a positive customer experience by maintaining a helpful and professional demeanor in all interactions.
Preferred Skills:
• Foundational understanding of Microsoft 365, Windows 10/11, and basic networking (TCP/IP, DNS, DHCP), application troubleshooting.
• Excellent verbal and written communication skills with an emphasis on client service.
• Experience with RMM/PSA tools (ConnectWise Manage, Automate, ScreenConnect) is a plus.
• Ability to follow defined processes and troubleshoot using checklists or SOPs.
• Strong time management and organizational skills.
• Commitment to continual learning and process improvement.
Experience:
• 1 to 2 years of experience in a help desk or technical support role preferred.
• Experience working in a Managed Service Provider (MSP) or multiclient support environment is a plus.
• Familiarity with ITIL principles is a bonus but not required.
Education:
• High school diploma or equivalent required.
• Associate degree in IT, Computer Science, or related field preferred.
• Relevant certifications such as CompTIA A+, Network+, or Microsoft Fundamentals are advantageous.