Senior Network & Linux Systems Engineer

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%)

• Monitor and troubleshoot site networks across our yard footprint

• Maintain VPN tunnels, firewall rules, and segmentation

• Improve alerting so we page humans only when humans can fix the problem

Linux fleet (~40%)

• Operate our edge fleet: NVIDIA Jetsons running CV inference, Ubuntu compute nodes, supporting hardware

• Own remote management, drift detection, OS patching, and secure baselines

• Lead the in-progress Windows-to-Linux migration and build provisioning automation that brings new sites online in hours

Automation (~20%)

• Eliminate repetitive ops work — AI agents wherever possible, scripts where not

• Strengthen observability for sites we can’t physically visit

• Contribute to our internal IT bot for routine access and config requests

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:

• 6–7+ years operating production Linux systems in mixed-environment fleets

• Deep practical networking — packet captures, routing, DNS, layer 2 vs. 3 reasoning without consulting a textbook

• Experience with edge or IoT device fleets (Jetson, Raspberry Pi, industrial PCs)

• Daily, fluent use of AI coding tools and agents

• Bash and Python scripting where automation is your default

• English working proficiency, written and spoken

Preferred Qualifications:

• Remote/distributed site operations (logistics, telecom, retail, industrial)

• Monitoring stacks (Prometheus, Grafana, Datadog) and Ansible

• GCP networking — VPCs, Cloud VPN, Cloud Interconnect, firewall rules

Our Stack:

GCP exclusively. NVIDIA Jetson and Ubuntu at the edge. GitHub with AI-assisted PR workflows (Copilot).

What We’re Looking For:

• 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

• Comfort working at the customer boundary — understanding how to integrate gracefully with customer networks, not just our own

• A hands-on IC mindset — no team underneath you, no deep org chart, just you and your peers on the infra team.

Location:

Remote — Latin America preferred

Working 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.