Remote Help Desk Technician

Remote Help Desk Technician

Location: Remote — United States

Department: Information Technology

Reports To: Director of Enterprise Technology & Security

Employment Type: Full-Time

Salary: $50,000–$65,000 annually

Build the Future of Transportation Technology

At Transit Technologies, we help transportation organizations improve safety, efficiency, compliance, and rider experience through innovative software and technology solutions. Our portfolio serves more than 4,000 customers and supports more than 100 million rides annually across public transit, school transportation, fleet operations, and mobility services.

We are looking for an experienced Remote Help Desk Technician who enjoys solving problems, helping people, and taking ownership from the first call through final resolution.

About the Opportunity

As a Remote Help Desk Technician, you will provide day-to-day technical support for our fully remote workforce of approximately 500 users.

You will be a primary point of contact for employees experiencing technology issues and will support Microsoft 365, Windows and macOS devices, user accounts, software applications, connectivity, hardware, and other end-user technology.

This is more than a ticket-routing role. We need someone who can independently diagnose and resolve issues, communicate clearly with users, document their work, and know when and how to engage internal IT, managed service providers, application vendors, security teams, and other escalation resources.

What You'll Do

• Provide remote technical support through phone, email, chat, screen sharing, and approved remote-support tools.
• Monitor, triage, prioritize, document, and resolve incidents and service requests in Jira ServiceDesk.
• Own user issues through resolution, providing timely updates and confirming successful outcomes.
• Troubleshoot Microsoft 365 applications and services, including Outlook, Exchange Online, Teams, SharePoint, OneDrive, authentication, licensing, and mail flow.
• Perform delegated administration and support within Microsoft Entra ID/Azure AD, Active Directory, Intune, Microsoft Defender, and Microsoft Purview.
• Handle user, group, password, account, and access-management tasks.
• Support Windows and macOS workstations, including operating systems, profiles, updates, endpoint configuration, printers, peripherals, and desktop applications.
• Install, configure, update, and troubleshoot approved software and business applications.
• Diagnose hardware, Wi-Fi, VPN, browser, network, printer, peripheral, and connectivity issues.
• Assist with onboarding, offboarding, account setup, equipment preparation, role changes, and access changes.
• Escalate advanced networking, infrastructure, security, application, and high-impact issues with complete diagnostic information.
• Coordinate with managed service providers and application vendors when outside escalation is required.
• Create and maintain knowledge-base articles, user instructions, and repeatable support procedures.
• Identify recurring issues and recommend improvements to documentation, training, self-service, and support processes.
• Protect company and customer information by following security, privacy, change-management, and access-control requirements.

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What You Bring

Required Qualifications

• 5+ years of hands-on IT support, help desk, service desk, or desktop-support experience; equivalent experience may be considered.
• Strong experience supporting Microsoft 365 and Windows environments.
• Hands-on experience supporting both Windows and macOS operating systems.
• Working knowledge of Jira ServiceDesk or a comparable IT service-management/ticketing platform.
• Experience troubleshooting hardware, printers, Wi-Fi, VPN, peripherals, software, and connectivity issues.
• Experience installing, configuring, updating, and troubleshooting software on end-user devices.
• Experience providing remote technical support using phone, email, chat, screen sharing, and remote-access tools.
• Strong troubleshooting, organization, prioritization, and time-management skills.
• Excellent customer-service and written and verbal communication skills.
• Ability to translate technical issues into clear, nontechnical explanations.
• Ability to work independently in a fully remote environment while collaborating effectively with internal teams and external partners.

Preferred Qualifications

• Microsoft 365 administration experience, including Exchange Online, Teams, SharePoint, OneDrive, Intune, Entra ID/Azure AD, Purview, or Defender.
• Endpoint management, device enrollment, software deployment, application packaging, patching, or remote-assistance experience.
• Familiarity with VPN, DNS, DHCP, TCP/IP, Wi-Fi, and basic network troubleshooting.
• Experience supporting a distributed or fully remote workforce.
• Experience working with managed service providers or vendor escalation processes.
• Familiarity with ITIL practices, service-level targets, knowledge management, and change control.
• CompTIA A+, Network+, Microsoft, or comparable certification.

The Ideal Candidate

You are the person others rely on when technology stops working. You don't immediately pass a difficult ticket to someone else—you investigate, ask the right questions, isolate the problem, and take ownership of getting it resolved.

You are comfortable troubleshooting Microsoft 365, supporting Windows and Mac devices, diagnosing connectivity issues, documenting solutions, and coordinating escalations when necessary.

Most importantly, you understand that great IT support isn't just about technology. It's about the experience of the person who needs your help.

What Success Looks Like

• Users receive timely, professional communication and effective resolutions.
• Common Microsoft 365, Windows, macOS, software, access, hardware, and connectivity issues are resolved efficiently whenever possible.
• Tickets are accurately prioritized, documented, and progressed through Jira ServiceDesk.
• Escalations contain the troubleshooting detail needed for rapid resolution.
• Knowledge articles and repeatable procedures reduce recurring issues and improve self-service.
• Security, privacy, and access-control requirements are consistently followed.

Our A-Player Attributes

At Transit Technologies, we look for people who don't just meet the requirements—they raise the standard.

Our A-Players:

• Drive Results — Deliver outcomes and follow through.
• Own It — Take accountability and act like an owner.
• Inspire & Elevate — Make the people around you better.
• Think Critically — Ask the right questions and solve problems thoughtfully.
• Communicate with Impact — Communicate clearly and effectively.
• Obsess Over Growth — Continuously learn and improve.
• Raise the Standard — Don't settle for "good enough."
• Stay Coachable — Seek feedback and adapt.

Why Join Transit Technologies?

You'll join a growing organization where technology matters, individual ownership is valued, and your work directly impacts employees across the company.

This is a 100% remote U.S. position. Employees are expected to be available during scheduled business hours and maintain a quiet, secure home workspace.

Benefits include medical, dental, and vision insurance; HSA options; company-paid life and AD&D coverage; voluntary life and disability coverage; Employee Assistance Program; 401(k) with company match; paid time off; sick leave; and company-paid holidays.

Benefits are subject to plan documents, eligibility requirements, waiting periods, applicable law, and annual plan changes.

Join Us

If you're an experienced help desk professional who takes ownership, enjoys solving problems, communicates exceptionally well, and believes great IT support should make technology easier for everyone, we'd like to hear from you.

Help us support the people who are building the future of transportation technology.

Transit Technologies is an Equal Opportunity Employer committed to providing equal employment opportunities to all qualified applicants and employees.