Principal Product Manager

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.

Our Gate Automation platform runs at the gates of some of the largest carriers and shippers in the country. As a Principal Product Manager, you will own major parts of that roadmap and act as a thinking partner on product architecture: how the pieces fit together as a suite, what the platform needs underneath, and what we build next.

The work spans edge hardware, computer vision, AI, and real-world operations. You will partner with engineering, ML, design, sales, implementation, and customers to automate truck yards, and you will prove the value in dollars a carrier's CFO will sign off on.

Priorities shift with customer contracts, pilots, and what we learn in the field. You will do well here if you can take an ambiguous problem, frame it, and drive a team to a shipped answer without waiting for someone to hand you requirements.

• Own product architecture across the suite: how gate automation, yard tracking, the customer portal, and integrations share data, workflows, and platform components.

• Lead discovery through customer interviews, on-site observation at terminals, and rapid prototyping.

• Turn customer problems into crisp definitions of value, scope, and success criteria, with a dollar ROI attached.

• Sequence the roadmap so most effort turns into revenue within the next few quarters while the platform keeps moving forward.

• Work with engineering and ML on architecture, APIs, data flows, and integration patterns.

• Write specs, acceptance criteria, and test plans with real technical rigor.

• Understand edge compute (NVIDIA Jetson), camera systems, OCR and vision pipelines, multi-sensor workflows, and voice and LLM agents.

• Hold the bar on reliability, accuracy, and performance in settings where a missed read stops a truck.

• Own the experience for drivers, guards, yard operators, and enterprise customers, from kiosk screens to the customer portal.

• Produce annotated wireframes, flows, and user stories. Prototype in code or with AI tools when that beats a mockup.

• Partner with product designers and engineers on a shared design system.

• Keep complex operational workflows simple to use.

• Coordinate across engineering, systems engineering, implementation, field operations, BI and data, sales, and support.

• Translate contract requirements and customer commitments into internal plans, and push back when a commitment does not add up.

• Run clean handoffs between product, deployment, and support.

• Serve as product lead in customer conversations with enterprise carriers and shippers.

• Run roadmap planning and sprint prioritization with engineering leads.

• Manage trade-offs across cost, timeline, accuracy, and scope.

• Set and report on KPIs for automation rate, detection accuracy, throughput, and uptime.

• Track rollout results and drive iteration.

• Act as a thought partner to the CTO on strategy, sequencing, and prioritization.

• Write documents people read and act on: PR/FAQs, specs, memos.

• Help build the PM practice at Outpost, including how we use AI across the product workflow.

• Embody Outpost's Values and Leadership Principles.

• 8+ years of product management, including products you took from 0 to 1 and on to scale, and platform-level products.

• Product architecture experience: you have defined how multiple products share a platform and made the calls that kept it coherent.

• Strong technical fluency in APIs, data systems, and system design. You can go deep on architecture and ML workflows with engineers.

• Strong UX product thinking, with shipped user flows that work for non-technical users.

• Experience in environments where hardware, software, and operations intersect.

• A record of owning ambiguous problems end to end with little direction.

• Clear writing, crisp documents, and strong meeting facilitation.

• Daily use of AI tools (Claude, ChatGPT, or similar) in your product work: research, specs, prototypes, analysis.

• Vision systems, edge computing, or industrial and IoT products.

• Freight, logistics, or transportation.

• Enterprise integrations (SFTP, REST APIs, SSO, EDI, TMS and YMS, ELD systems).

• Voice AI or LLM agent products.

• Comfort on-site around trucks, gates, and industrial yards.

• You own the roadmap for a major part of the Outpost product suite, and the team trusts your calls.

• A documented product architecture that engineering builds against.

• Shorter cycle time from customer feedback to spec to deployment.

• Automation rates at deployed sites climbing, measured and reported.

• Strong working relationships with engineering, implementation, sales, and operations.

• Clean division of ownership with the other PM, with the whole suite covered.