Help Desk Specialist II

About Us

IT TechPros is a Managed Service Provider built on the belief that IT should be simple, reliable, and genuinely helpful. We know how nuanced technology can be, and that’s why it’s our goal to make it work seamlessly for your business.

We see our clients as partners, not tickets in a queue. Our team delivers a premium level of support that helps your people feel supported, confident, and productive while we manage the complexity behind the scenes. By connecting the tools you depend on with the people who use them every day, we make IT feel more human, dependable, and stress-free. 

Overview

The Help Desk II Technician is a mid-level IT support role designed for professionals with hands-on technical experience and strong customer-facing skills. This position builds on Help Desk I responsibilities and requires deeper technical knowledge, greater autonomy, and the ability to troubleshoot and resolve more complex issues across systems, networks, and applications. Help Desk II technicians handle escalations from Help Desk I for issues that require greater technical depth and experience, while continuing to support reliable, secure, and efficient IT environments.

Key Responsibilities

• Provide advanced technical support for desktops, laptops, mobile devices, operating systems, and business applications
• Receive and resolve escalated tickets from Help Desk I that require deeper technical investigation
• Troubleshoot hardware, software, network connectivity, and performance issues both remotely and onsite
• Traveling to client locations to assist with hands-on troubleshooting (all client sites are within 20 miles of the office)
• Support Windows and macOS environments, including user profiles, system configurations, and OS-level troubleshooting
• Manage and support Microsoft 365, including Exchange, Teams, SharePoint, and OneDrive
• Assist with user account management in Active Directory and Azure AD, including permissions, group policies, and password issues
• Identify recurring issues and recommend long-term fixes or process improvements
• Document solutions, troubleshooting steps, and known issues in the ticketing system and internal knowledge base
• Communicate clearly with end users, setting expectations and providing timely updates
• Support onboarding and offboarding processes, including device setup and access provisioning
• Assist with patching, updates, and basic security tasks under established procedures
• Participate in an on-call rotation, including occasional weekend coverage, to support client needs
• Collaborate with senior engineers and other departments on projects and larger technical initiatives

Required Skills and Experience

• 2-5 years of experience in a help desk or technical support role
• Strong working knowledge of Windows operating systems and basic macOS support
• Experience supporting Microsoft 365 and common business productivity tools
• Solid understanding of networking fundamentals such as DNS, DHCP, TCP/IP, VPNs, and Wi-Fi
• Hands-on experience with Active Directory and basic Azure AD administration
• Familiarity with endpoint management, remote support tools, and ticketing systems
• Proven ability to troubleshoot independently and manage multiple issues at once
• Strong customer service skills with experience interacting directly with end users
• Ability to explain technical concepts clearly to non-technical audiences

Preferred Qualifications

• Experience in an MSP or fast-paced support environment
• Exposure to security best practices, endpoint protection, and access controls
• Basic scripting or automation experience 
• Relevant certifications such as CompTIA A , Network , Microsoft, or equivalent experience

What Success Looks Like in This Role

• Issues are resolved efficiently with minimal escalation
• End users feel supported, informed, and confident in the help they receive
• Documentation is clear, accurate, and consistently maintained
• Technical judgment improves system reliability and reduces repeat issues
• The technician operates with confidence, ownership, and accountability

Why Work at IT TechPros

IT TechPros is a place to build real technical experience and move your career forward. This role offers hands-on exposure to more complex IT environments, direct collaboration with senior engineers and cybersecurity professionals, and participation in projects that deepen your technical skills. Strong performance leads to expanded responsibilities, deeper specialization, and clear paths into senior support or cybersecurity-focused roles.

We also focus on creating a workplace where people are supported and equipped to do their best work:

• Health and dental coverage for you and your family
• Generous vacation time that increases with tenure, allowing you to disconnect and recharge
• Company laptop and phone stipend to stay equipped and connected
• Ongoing training and certification support to continue building your skills
• Real-world experience with a well-established MSP and opportunities for career advancement
• Team lunches and seasonal events at some of San Diego’s best spots

Reporting Structure

This role reports to the Chief Technology Officer and works closely with senior engineers and other technical teams.

Salary : $22 - $27