Autonomy Operations Architect

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.