M365 & AI Administrator

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 You will serve as a hands-on administrator responsible for configuring and maintaining the organization’s Microsoft 365 Copilot environment. Working under the direction of IT leadership, you will manage technical settings that govern Copilot functionality, access, and licensing. This role focuses on executing established policies while escalating decisions related to architecture, vendor strategy, and governance frameworks. You will ensure Copilot operates efficiently and securely while identifying risks and opportunities for leadership review. Essential Responsibilities Copilot Configuration & Administration Configure and maintain Copilot using the Microsoft 365 Admin Center and Copilot Control System Execute day-to-day system settings, feature toggles, and configuration updates as directed by IT leadership Ensure Copilot operates reliably, securely, and in alignment with defined policies License & Access Management Manage Copilot license allocation and revocation using security groups Monitor license utilization via the Copilot Dashboard Identify and flag underutilized licenses for reallocation Security & Governance Enforcement Implement sensitivity labels, access controls, and SharePoint permissions aligned with governance frameworks Identify and remediate overly permissive access that may expose sensitive data through Copilot Support enforcement of data protection and compliance standards within M365 Monitoring, Reporting & Escalation Monitor Copilot usage telemetry and generate regular reports for IT leadership Track license counts and contract renewal timelines Identify trends, anomalies, and adoption gaps Surface recommendations while deferring architectural and vendor decisions to leadership AI Tool Oversight & Deployment Support Monitor usage of secondary AI tools (e.g., ChatGPT Business for marketing) against acceptable use policies Escalate policy violations or data handling concerns to management Support deployment of custom AI agents in Copilot Studio, including testing configurations and verifying access controls Document deployment procedures and technical processes Qualifications 3–5 years of experience administering Microsoft 365 environments (Admin Center, Entra ID, security groups, access policies) Hands-on experience with Microsoft 365 Copilot configuration, including the Copilot Control System, license management, and Copilot Dashboard Strong understanding of access controls, sensitivity labels, and data loss prevention within the M365 ecosystem Experience with role-based access control (RBAC) Ability to document technical procedures clearly and communicate status updates effectively Experience with Copilot Studio for building or managing custom AI agents Experience working with IT leadership, security and compliance teams, and business users across departments Eligible to work in the United States Bonus Points For Basic understanding of API authentication (OAuth 2.0, REST APIs) Experience with Microsoft Purview or similar compliance tools Familiarity with Privileged Identity Management (PIM) Relevant certifications such as MS-4006 or MS-102 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. Paid parental leave. 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. Company-wide bonus and commission plans. 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.