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Senior Network & Linux Systems Engineer

June 2, 2026

About Us:Outpost is building the backbone of freight. We’re reinventing how supply chain infrastructure works in America with carrier agnostic truck terminals. As a vertically integrated real estate, operations, and technology company, we acquire and operate mission-critical real estate across the country to serve the largest logistics providers in the world. Backed by $1B from Greenpoint Partners, we’re scaling and building the most valuable logistics network in the country.We thrive on accountability, integrity, and a shared drive to raise the bar. If you’re excited to reshape the industry alongside a high-performance team with a championship mindset that executes relentlessly, welcome aboard.Role Summary:You’ll join a small but highly capable team focused on field infrastructure, working hands-on to keep our network and Linux fleet healthy as we scale.Project Details:Network operations (~40%)<ul style="min-height:1.5em"><li>Monitor and troubleshoot site networks across our yard footprint</li><li>Maintain VPN tunnels, firewall rules, and segmentation</li><li>Improve alerting so we page humans only when humans can fix the problem</li></ul>Linux fleet (~40%)<ul style="min-height:1.5em"><li>Operate our edge fleet: NVIDIA Jetsons running CV inference, Ubuntu compute nodes, supporting hardware</li><li>Own remote management, drift detection, OS patching, and secure baselines</li><li>Lead the in-progress Windows-to-Linux migration and build provisioning automation that brings new sites online in hours</li></ul>Automation (~20%)<ul style="min-height:1.5em"><li>Eliminate repetitive ops work — AI agents wherever possible, scripts where not</li><li>Strengthen observability for sites we can’t physically visit</li><li>Contribute to our internal IT bot for routine access and config requests</li></ul>How You Work:This is non-negotiable: you already use AI tooling extensively in your day-to-day. You write code with Claude Code, Codex, or Cursor, you delegate real work to AI agents, and you have opinions about which tools work for which tasks. Vibe coding is fine; building agentic workflows that handle ops tasks end-to-end is better.In your application, tell us which AI tools you use daily, one concrete agent or workflow you built that saved you real time, and a task you no longer do manually because you delegated it to an LLM. Applications without a substantive answer here will not move forward.Qualifications:<ul style="min-height:1.5em"><li>6–7+ years operating production Linux systems in mixed-environment fleets</li><li>Deep practical networking — packet captures, routing, DNS, layer 2 vs. 3 reasoning without consulting a textbook</li><li>Experience with edge or IoT device fleets (Jetson, Raspberry Pi, industrial PCs)</li><li>Daily, fluent use of AI coding tools and agents</li><li>Bash and Python scripting where automation is your default</li><li>English working proficiency, written and spoken</li></ul>Preferred Qualifications:<ul style="min-height:1.5em"><li>Remote/distributed site operations (logistics, telecom, retail, industrial)</li><li>Monitoring stacks (Prometheus, Grafana, Datadog) and Ansible</li><li>GCP networking — VPCs, Cloud VPN, Cloud Interconnect, firewall rules</li></ul>Our Stack:GCP exclusively. NVIDIA Jetson and Ubuntu at the edge. GitHub with AI-assisted PR workflows (Copilot).What We’re Looking For:<ul style="min-height:1.5em"><li>Strong operators who can also reason about design — you won't whiteboard architecture from scratch, but you'll engage in design conversations as we evolve our infrastructure</li><li>Comfort working at the customer boundary — understanding how to integrate gracefully with customer networks, not just our own</li><li>A hands-on IC mindset — no team underneath you, no deep org chart, just you and your peers on the infra team.</li></ul>Location:Remote — Latin America preferredWorking Arrangements:This role is a full-time contract position. You’ll work closely with our core engineering team — embedded in our sprints, standups, and Slack channels — but employment is managed through the agency. We’ve built this model successfully with engineers in Latin America, and it’s been a great fit for both sides.Outpost is an Equal Opportunity Employer and Prohibits Discrimination of Any Kind.

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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...

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