Autonomy Operations Architect

Cartage is an AI operating system for shippers & 3PLs that automates routine tasks and connects users to carriers.

Location: Vancouver
Company size: 1–20
Posted: 1mo ago
Via: Yc

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Job listing · Updated 22 AUG 2026

Autonomy Operations Architect

Cartage· Vancouver, BC, CA / Vancouver, British Columbia, CA / San Francisco, CA, USView company profile

Job title: Autonomy Operations Architect
Job location: Vancouver, BC, CA / Vancouver, British Columbia, CA / San Francisco, CA, US
Job listing URL: https://www.ycombinator.com/companies/cartage/jobs/LDjKBtk-autonomy-operations-architect
Job description: # Autonomy Operations Architect **Location:** Vancouver (preferred) / San Francisco\ **Team:** Autonomy Operations\ **Reports to:** Head of Autonomy Operations (Kolby) --- ## About Cartage Cartage is building an autonomy-first logistics AI called **Wilson**. Wilson acts as a 24/7 logistics team for manufacturers and distributors — behaving closer to a human employee than traditional software. Our goal is not to help humans do logistics better.\ Our goal is to **build an AI that actually does the work**. We believe autonomy is a **measured capability**, not a marketing claim.\ That belief shapes how we build product, how we sell, and how we run the company. This role exists to keep that belief true. --- ## What Autonomy Operations Does Autonomy Operations exists to answer one question: > **“What is Wilson actually capable of today — and where does he break?”** This team does **not** run logistics.\ It does **not** quietly fix things.\ It does **not** hide human work. Instead, it: * Surfaces reality * Enforces boundaries * Turns failures into signal for Product and Engineering --- ## The Role As an **Autonomy Operations Architect**, you sit at the boundary between real-world logistics and Wilson. You will monitor live workflows, identify where autonomy breaks, and step in **only when necessary** — not to take over the work, but to **manage Wilson’s execution** and make failures visible. You are not doing the work yourself.\ You are ensuring Wilson either does it correctly — or that the system clearly records when he cannot. This is a technical, analytical, **logistics-native** role — not customer support and not day-to-day operations. --- ## What You’ll Own * Monitoring live shipments and workflows * Identifying when and where autonomy breaks * Assigning and adjusting autonomy levels when humans intervene * Stepping in to manage Wilson when required (not replacing him) * Classifying failures and exceptions with precision * Enforcing supported vs unsupported workflows * Producing clear, actionable signal for Product and Engineering * Maintaining the autonomy matrix and weekly reality reports You are successful when: * Failures surface quickly * Nothing is “quietly handled” * Product and Engineering are never surprised by reality --- ## What You Will _Not_ Own * Making workflows succeed at all costs * Long-term manual execution * Running accounts end-to-end * Custom customer workarounds * “Saving” deals or shipments * Writing production engineering code If a workflow can’t run autonomously, your job is to **expose that**, not mask it. --- ## Who This Role Is For This role is a strong fit if you: * Have worked in logistics operations at a **shipper, distributor, or freight brokerage** * Understand how shipments actually move — and how they fail * Enjoy finding where systems break * Are comfortable saying “this doesn’t work yet” * Care about correctness more than optics * Think clearly under ambiguity * Like being close to real operations without owning outcomes You don’t need to be a traditional engineer, but you do need: * Strong systems thinking * Comfort with data, workflows, and edge cases * Clear written communication --- ## Who This Role Is _Not_ For This role is **not** a fit if you: * Want to run logistics day-to-day * Prefer to quietly fix problems * Measure success by “things got done” * Want to promise customers anything it takes * Are uncomfortable with failure being visible --- ## Why This Role Matters Most companies hide human labor behind AI.\ We don’t. Autonomy Operations is how we stay honest — and how the system actually improves. If this role is done well, the company compounds.\ If it isn’t, we become a services business. That’s how important this role is. --- ## Compensation Competitive salary + meaningful equity.\ Exact numbers depend on experience, scope, and location.

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