We Speak Safety and Efficiency:
In September of 2024, Bestpass, Fleetworthy, ExpressTruckTax and Drivewyze rebranded as Fleetworthy. This rebrand reflects our ongoing mission to simplify fleet safety, compliance, and toll management under one unified brand.
Fleetworthy is revolutionizing road safety and fleet management with a command center for safety, compliance, and efficiency. Our connected suite provides real-time insights and control, enabling customers to maximize efficiency, reduce risk, and save money.
With technology that unifies safety, compliance, toll management, weigh station bypass, and more, Fleetworthy empowers organizations to perform at their best. We simplify operations to ensure every vehicle and driver is not just compliant, but beyond compliant. Supporting millions of drivers and vehicles, Fleetworthy is leading a new era in road safety and fleet technology.
At Fleetworthy, you’re in the driver’s seat!
We’re looking for a skilled Systems Engineer to maintain and support our internal IT infrastructure, systems, and cloud environments. This role is critical to ensuring smooth operations across endpoints, servers, and virtual infrastructure. The ideal candidate brings strong troubleshooting ability, a systems mindset, and experience supporting hybrid environments across on-prem and cloud.
Core Responsibilities
System & Server Administration
- Administer Windows and Linux systems across on-prem and cloud environments.
- Support and maintain virtual infrastructure including VMware ESXi and vCenter.
- Manage system patching, updates, backups, and performance monitoring.
- Maintain user account provisioning, deprovisioning, and RBAC controls.
Cloud Infrastructure Support
- Support daily operations in AWS and/or Azure environments (e.g., EC2, IAM, VPC).
- Assist in backup, recovery, and storage configuration for cloud workloads.
- Apply cloud cost controls and resource optimization practices.
Security & Access
- Enforce endpoint protection, MFA, and least privilege access standards.
- Support group policy management, SSO, and user access reviews.
- Administer and document account creation, permission changes, and deprovisioning in line with ISO 27001 standards for access control.
- Collaborate with Security team on periodic access reviews and privileged account audits.
Monitoring & Incident Response
- Operate and maintain system monitoring and alerting tools.
- Triage infrastructure-related tickets and participate in incident workflows.
- Document changes and maintain system health dashboards.
Internal Tools & Support Escalation
- Support internal productivity tools (e.g., Google Workspace, M365, VPNs).
- Act as Tier 3 support for escalated issues from the Help Desk.
- Document systems procedures and support onboarding/offboarding.
Skills & Qualifications
Required
- 4+ years in a Systems Administrator, Infrastructure, or IT Operations role.
- Proficiency with Windows and Linux systems.
- Experience administering VMware ESXi and vCenter environments.
- Familiarity with AWS and/or Azure administration.
- Competence with IAM, GPO, and endpoint security tools.
- Scripting skills (PowerShell, Bash, or Python).
Preferred
- Experience with endpoint management tools (Intune, Jamf, CrowdStrike).
- Knowledge of compliance frameworks like SOC 2 or ISO 27001.
- M365 administration and familiarity with SSO/IAM integrations.
- Experience supporting hybrid environments (cloud/on-prem).
- Network administration or troubleshooting experience (e.g., Cisco switches, firewalls, VLANs).
Ideal Candidate
- Reliable systems administrator who ensures infrastructure stability and uptime.
- Works cross-functionally with IT, Security, and Engineering teams.
- Proactive about monitoring, automation, and security hygiene.
- Clear communicator and documentation-oriented.
Compensation
$65,000 to $75,000 USD Yearly
What Drives Us to Work Every Day:
- We pride ourselves on making a difference, for our employees, clients, and their businesses.
- We accept team members for who they are and what they bring to the table.
- We are proud to build all our relationships based on transparency and trust.
- We are a team of energetic and curious individuals passionate about the work we do every day!
Our Core Values – We are 1TEAM
- People 1st - People 1st! We win as a team by collaborating, having each other’s backs, and bringing out the best in each other. We always treat others as they would like to be treated.
- Trust - We inspire trust by delivering on our promises, owning outcomes, being transparent in our communications, and acting with integrity.
- Every Trip Matters - Because every trip that our customers take is important to them, it's important to us. Whether it is a load being hauled across the country or a service vehicle traveling on a toll road, our customers count on us to deliver the right expertise, software, and data to make every trip safe, efficient, and productive.
- Always Innovating - We solve for the customer and focus on outcomes. We are nimble in our approach. When we fail, we fail fast and learn from it. We are here to disrupt, not to fit in.
- Mindset - We are committed to a growth mindset. Our efforts and attitudes are what determine our abilities. We embrace good criticism. We seek new challenges. We never stop learning.
About Bestpass: Bestpass is a comprehensive payment platform provider and leader in toll management solutions for commercial fleets of all sizes. Bestpass saves fleets time and money by consolidating payments and providing insight into cost per vehicle. Bestpass, founded in 2001, covers 100% of major toll roads across the U.S., supports more than 30,000 customers, and processes over $1.5 billion in toll transactions annually. Bestpass offers a range of toll coverage options for owner-operators, regional fleets, and national fleets, as well as customized solutions for specific needs.
About Fleetworthy Solutions: Fleetworthy Solutions, Inc. provides DOT safety and regulatory compliance services to commercial fleets that take them Beyond Compliant. Fleetworthy combines exceptional client service, advanced technologies, and more than 40 years of transportation industry expertise to make sure that drivers and assets are truly fleetworthy. The company helps private fleets, for-hire carriers and third-party logistics companies of all sizes surpass compliance of federal, state, and local regulations and streamline processes to reduce costs and mitigate risks.
Fleetworthy is committed to fostering a diverse and inclusive culture that is respectful and welcoming of individual differences. We are proud to be an equal opportunity employer and all qualified applicants will receive consideration for employment without regard to race, color, religion or belief (or lack thereof), sex, nationality, national or ethnic origin, civil status, age, citizenship status, sexual orientation, disability, genetic information, familial status, marital or registered civil partnership status, pregnancy or maternity status, gender identity, gender reassignment, military or veteran status, or any other protected characteristic in accordance with applicable laws and regulations
Top Skills
What We Do
Bestpass is the comprehensive payment platform provider and leader in toll management solutions for commercial fleets of all shapes and sizes. With more than 30,000 customers and processing more than $1.5 billion in toll transactions in the United States and Canada, Bestpass ensures data accuracy, consolidates payments, and saves its users time and money. Founded in 2001 by truckers for truckers, we are a trusted partner on the road and in the back office for customers and tolling authorities. To learn more, visit www.bestpass.com.
