Remote Delivery Pilot Jobs in Chicago, IL (NOW HIRING)

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:

Our platform combines AI-powered gate automation, computer vision, and operational software to help logistics operators run smarter, faster facilities. We're a small, high-conviction team shipping real technology that ends up in real yards, at real gates, moving real freight; if our system goes down, trucks stop moving and a customer's yard stops running. What we build is mission-critical to the people who depend on it.

We’re scaling quickly, and the physical systems supporting our platform must be reliable, repeatable, and remotely manageable as our site footprint grows. We need a Senior Edge Systems Engineer to own the architecture of our kiosks, edge compute systems, networking, power, cameras, access systems, and other on-site technology—from initial design and validation through deployment and long-term fleet management.

Key Responsibilities:

• Own the end-to-end edge systems architecture for Outpost kiosks and other site technology systems.

• Develop reference designs and standards covering edge compute, networking, power, displays, cameras, access systems, peripherals, cabling, mounting, and supporting infrastructure.

• Evaluate, select, and qualify hardware platforms, components, vendors, and deployment approaches.

• Design reliable power and recovery systems, including power supplies, PoE, distribution, backup power, managed reboot capabilities, watchdogs, and out-of-band access.

• Own edge compute standards across Ubuntu, NVIDIA Jetson, industrial PCs, embedded systems, storage, networking, thermal management, enclosures, and connected peripherals.

• Define how distributed systems are provisioned, configured, monitored, patched, inventoried, updated, remotely accessed, recovered, and replaced at scale.

• Build and test prototypes, proof-of-concept systems, and design revisions before broader deployment, including failure and recovery testing.

• Create bills of materials, diagrams, specifications, installation standards, validation procedures, and troubleshooting documentation.

• Partner with Linux, network, software, security, product, and Field Operations teams to deliver cohesive and supportable systems.

• Support pilot deployments and occasional field installations to validate designs under real-world conditions.

• Investigate recurring failures and turn root causes into improvements in architecture, component selection, automation, and deployment processes.

• Manage hardware lifecycle concerns, including revisions, substitutions, spares, vendor alternatives, obsolescence, and replacement standards.

• Participate in an on-call rotation.

What You Can Expect:

• Real ownership over the edge systems architecture supporting technology deployed at physical gates and commercial truck yards.

• Work on systems where reliability and recoverability have an immediate operational impact on customers.

• The opportunity to establish hardware and fleet-management standards that scale from prototypes to a growing distributed deployment.

• A mix of architecture, hands-on engineering, lab validation, troubleshooting, and occasional field work.

• A small team that moves quickly, argues in good faith, and trusts engineers to make decisions.

• Problems grounded in the physical world: power, compute, networks, cameras, gates, trucks, and yards.

Qualifications:

• 5+ years in hardware systems, embedded systems, edge infrastructure, or a similar engineering role supporting production deployments.

• Experience serving as the technical owner for an integrated hardware platform or distributed site architecture.

• Hands-on experience with Ubuntu-based edge systems, embedded Linux, and NVIDIA Jetson platforms.

• Experience designing and supporting industrial computers, embedded PCs, single-board computers, or GPU-enabled edge systems.

• Strong understanding of power supplies, PoE, power distribution, backup power, remote power management, and recovery from power interruptions.

• Experience deploying and managing fleets of remote, embedded, or unattended systems at scale.

• Experience with automated provisioning, configuration management, monitoring, patching, asset inventory, staged deployments, and remote recovery.

• Working knowledge of Ethernet networking, IP addressing, switching, routing, VPNs, and cellular connectivity.

• Experience integrating compute platforms, networking equipment, displays, cameras, sensors, and other connected peripherals.

• Ability to troubleshoot across hardware, firmware, operating systems, networks, and applications.

• Track record of moving systems from prototype through pilot deployment and into repeatable production.

• Strong communication and documentation skills, with the ability to work across technical and non-technical teams and independently own ambiguous problems.

Preferred Qualifications:

• Experience with kiosks, machine vision, security cameras, access control, industrial automation, or IoT systems.

• Experience designing enclosures, mounting systems, thermal solutions, or equipment for outdoor and semi-controlled environments.

• Experience with environmental, failure-mode, or reliability testing.

• Familiarity with Secure Boot, TPM-backed capabilities, disk encryption, certificate management, and other edge-device security practices.

• Experience working closely with field technicians, manufacturers, vendors, or distributed installation teams.

Our Stack:

Ubuntu · NVIDIA Jetson · Industrial PCs and Edge Compute · Tailscale · Teltonika · Ubiquiti · PoE · Cameras and Access Control

Benefits:

• Title Commensurate with Experience

• Comprehensive Benefits Package including Health, Dental, and Vision Insurance

• 401(k) Retirement Plan Matching

• 18 Paid Holidays

• Unlimited PTO

• Friday Team Lunches

• Base salary range: $135,000 – $160,000 annually, depending on experience and qualifications. Total compensation includes a discretionary bonus; a complete compensation and benefits summary will be provided during the interview process.

Outpost is an Equal Opportunity Employer and Prohibits Discrimination of Any Kind.