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Lead Infrastructure Architect

June 2, 2026

<div class="content-intro">Fleetworthy offers the only complete technology suite for fleet readiness, uniting safety and compliance, toll management, and weigh station bypass solutions. We help fleets streamline operations, control costs, and operate with confidence. Trusted by 75% of the top fleets in North America, Fleetworthy offers the most adopted toll management solution and largest weigh station bypass network. Going beyond regulatory requirements, our safety and compliance capabilities strengthen safety programs and enable proactive audit readiness. We support millions of vehicles and drivers and are recognized across the industry for innovation and leadership. Fleetworthy is shaping the future of fleet readiness with AI-enabled, connected fleet technology that keeps drivers safe, fleets compliant, and operations running at peak efficiency. Learn more at <a class="Hyperlink SCXW248234814 BCX0" href="http://fleetworthy.com/" target="_blank">fleetworthy.com</a>.</div>Role Summary The Staff Infrastructure Architect is a senior individual contributor reporting directly to the CTO. This role defines the standards for how Fleetworthy's production environments are designed, operate, and connect, covering infrastructure architecture, networking between systems, reliability, observability, and AI infrastructure and platforming. Standards set here are implemented across the organization. This role is a peer to the Staff Software Architect. One owns how applications are built, the other owns how the environments they run on are designed and operated. Neither owns delivery. Both set the standards the organizations execute against. Key Areas of Responsibility <ul> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Define and own the infrastructure architecture vision across Fleetworthy's production environments, including how systems are designed, connected, and operated</li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Establish centralized observability standards adopted across all teams</li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Define standards for how AI workloads are hosted, scaled, and integrated across the organization</li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Advise on security architecture, partnering with the security manager to ensure infrastructure decisions align with compliance requirements</li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Work alongside embedded architects in Technical Operations, setting standards and providing guidance</li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Partner closely with the Staff Software Architect to maintain clear, complementary standards across both domains</li> </ul> What We Are Looking For <ul> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Deep expertise in infrastructure architecture, production systems design, and networking</li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Strong background in observability, reliability engineering, automation, and production operations at scale</li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Experience with AI infrastructure and platforming, with an eye toward architecture and security alignment</li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Ability to define and socialize standards across multiple teams</li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Strong prioritization skills, with a track record of focusing on the changes that will have the most meaningful impact</li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Ability to influence and align across teams</li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Demonstrated empathy for the teams implementing the standards they set, understanding and caring about the cost and impact of architectural decisions on others</li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Clear communicator across infrastructure, development, and non-technical audiences</li> </ul> What Success Looks Like <ul> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Production environment standards are clearly defined and consistently adopted across the organization</li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Observability is centralized and providing meaningful operational visibility across all platforms</li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">AI infrastructure and platform patterns are established with clear architecture and security alignment</li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">The boundary with the Staff Software Architect is clear, with no ambiguity about ownership</li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Embedded architects and leadership across the organization view this role as a trusted resource and point of clarity on infrastructure decisions</li> <li style="font-family: arial, helvetica, sans-serif; font-size: 12pt;">Security is embedded in how infrastructure is designed, not addressed after the fact</li> </ul><div class="content-conclusion">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.</div>

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...