Service Desk Support Analyst II - Minneapolis, MN

Road Safety Services, Inc. (RSS) is the second-largest provider of highway striping and pavement markings for roads and parking lots across the United States. We value safety, quality, and integrity in everything we do. As our company continues to grow through both acquisition and expansion, we're looking for a Service Desk Support Analyst II who can solve complex technical problems both remotely and in the field.

We are also looking for someone who is comfortable using AI tools as part of their daily workflow. The ideal candidate already leverages tools like Microsoft Copilot, ChatGPT, or Claude to research issues, create documentation, develop scripts, and improve efficiency while exercising sound judgment and validating results.

The Service Desk Support Analyst II provides advanced technical support across more than 50 locations and multiple operating companies. This role combines remote service desk support with hands‑on field work, supporting end users, infrastructure, Microsoft cloud technologies, and IT projects. Success in this role requires strong troubleshooting skills, initiative, and a mindset focused on continuous improvement through automation and AI.

• Provide remote support via phone, email, and remote access tools.
• Troubleshoot and resolve complex hardware, software, network, and system issues.
• Document incidents, resolutions, and troubleshooting steps in the ticketing system.
• Use AI tools to accelerate research, diagnostics, scripting, and documentation while validating outputs before implementation.

• Provide on‑site support at offices and operational locations.
• Install, upgrade, repair, and replace computers, servers, printers, and peripherals.
• Configure and maintain network equipment including switches, routers, wireless devices, and cabling.
• Support office relocations, expansions, and new site launches.

• Administer and troubleshoot Microsoft Entra  Microsoft 365.
• Manage user provisioning, access controls, groups, SSO, and MFA.
• Maintain security best practices and user access governance.

• Identify opportunities to automate repetitive tasks using Power Shell, Power Automate, or similar tools.
• Create and maintain documentation, knowledge base articles, and technical procedures.
• Analyze support trends and recommend improvements to processes, technology, and service delivery.

• Partner with IT team members and business stakeholders to resolve escalated issues.
• Mentor Tier I support staff and share best practices.
• Participate in projects supporting company growth, acquisitions, and operational efficiency.

• 4+ years of IT support experience, including at least 2 years in a Tier II or similar role.
• Experience administering and troubleshooting Microsoft Entra  (Azure AD).
• Experience supporting Microsoft 365 environments.
• Strong knowledge of Windows operating systems, hardware support, and networking fundamentals.
• Experience with ticketing systems, remote support tools, and IT asset management.
• Demonstrated ability to balance remote support with hands‑on field work.
• Experience using AI tools such as Copilot, ChatGPT, or Claude to improve productivity.
• Strong troubleshooting, communication, and customer service skills.
• Valid driver's license and ability to travel.

• Experience supporting multi‑site organizations.
• Power Shell, Power Automate, or other automation experience.
• Experience with networking infrastructure and office buildouts.
• CompTIA, Microsoft, ITIL, or similar certifications.
• Experience supporting hybrid and cloud-based environments.

• Approximately 25% overnight travel throughout the United States.

At RSS, you'll support a growing nationwide organization, work with modern technologies, and play a key role in keeping our teams productive and connected. We encourage innovation, continuous learning, and practical use of AI and automation to improve how work gets done.

Road Safety Services, Inc. is an Equal Opportunity Employer.