Senior IT Helpdesk Specialist

About PrePass

PrePass® is North America's most trusted weigh station bypass and toll management platform. We’re transforming how the transportation industry operates, creating solutions that keep trucks moving safely, efficiently, and compliantly. This means making bold decisions and building systems that support not only fleets but the broader economy. It all starts with enabling commercial vehicles to keep rolling with seamless toll management, weigh station bypass, and safety solutions. It’s what we do best, and we do it to meet the demands of the road every day.

That’s why people join us: our solutions are implemented in real-time, on highways and interstates across the nation, helping fleets go farther, faster. This work challenges and rewards, presenting complex problems that need ambitious answers. We hire bold thinkers with a heart for impact, a passion for progress, and the optimism to shape the future of transportation.

About the Role

The Senior IT Helpdesk Specialist serves as the primary escalation point for complex technical issues, ensuring timely resolution and exceptional customer service. This role involves advanced troubleshooting, mentoring junior technicians, and improving IT processes. The specialist will manage hardware, software, and network-related issues across Windows and macOS platforms, iOS and Android devices, and Office 365 services, ensuring minimal downtime and optimal system performance. This is a hybrid role based at our downtown Phoenix office.

Key Responsibilities

Advanced Technical Support

• Diagnose and resolve complex hardware, software, and network issues for Mac and PC systems, as well as iOS and Android devices, both remotely and on-site.
• Handle escalated tickets from Level 1 and Level 2 support teams.

System Administration & Tools

• Manage user accounts, permissions, and security settings in Office 365 and Active Directory.
• Administer and support Jira Service Management for ticketing and workflow.
• Manage Apple Business Manager for macOS and iOS device enrollment and provisioning.
• Configure and maintain Microsoft Intune for device management and compliance across Windows, macOS, iOS, and Android.

Office 365 Support

• Provide advanced support for Microsoft 365 apps and services (Exchange Online, Teams, SharePoint, OneDrive).
• Assist with mailbox management, distribution lists, and security policies.

Process & Documentation

• Maintain accurate records in the ticketing system, documenting resolutions and best practices.
• Develop and update knowledge base articles and technical documentation for cross-platform and Office 365 support.

Collaboration & Mentorship

• Provide guidance and training to junior helpdesk staff.
• Collaborate with infrastructure, security, and application teams to resolve systemic issues.

Continuous Improvement

• Identify recurring issues and recommend process or technology improvements.
• Participate in IT projects, system upgrades, and deployment initiatives for multi-platform environments.

Requirements

Qualifications

Education

• Bachelor’s degree in information technology, Computer Science, or related field (or equivalent experience).

Experience

• 4–6 years in IT helpdesk or technical support roles, with at least 2 years in a senior or escalation capacity.

Technical Skills:

• Strong knowledge of Windows and macOS environments, Office 365 administration, and networking fundamentals.

• Proficiency with Jira Service Management, Apple Business Manager, and Microsoft Intune.

• Experience supporting iOS and Android mobile devices.

• Familiarity with security best practices and endpoint protection tools.

Certifications (Preferred)

• CompTIA A+, Network+, Security+, or Microsoft Certified: Modern Desktop Administrator Associate.
• Apple Certified Support Professional (ACSP) or equivalent is a plus.

Soft Skills

• Excellent problem-solving, communication, and organizational skills.
• Ability to work independently and mentor team members effectively.

Benefits

How We Will Take Care of You

• Robust benefit package that includes medical, dental, and vision that start on date of hire.
• Paid Time Off, to include vacation, sick, holidays, and floating holidays.
• 401(k) plan with employer match.
• Company-funded “lifestyle account” upon date of hire for you to apply toward your physical and mental well-being (i.e., ski passes, retreats, gym memberships).
• Tuition Reimbursement Program.
• Voluntary benefits, to include but not limited to Legal and Pet Discounts.
• Employee Assistance Program (available at no cost to you).
• Company-sponsored and funded “Culture Team” that focuses on the Physical, Mental, and Professional well-being of employees.
• Community Give-Back initiatives.
• Culture that focuses on employee development initiatives.

Join Us

At PrePass, our mission drives us.

We invest in relationships. We challenge ourselves to innovate and improve. We win together. Simply put, we live our Core Values.

Ready to help move the transportation industry forward? Join us and let’s drive progress—together.