Autonomy Operations Analyst

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 Analyst, 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.