Head of Pilot Operations

Roboticsconnected; New York (NY); Hybrid; USD 180,000 - 240,000; Full time

Job summary

Ultra is seeking a Pilot Operations Lead to build and run a scalable teleoperation program in the U.S. You will own training, staffing, and quality for pilots while overseeing a multi‑million‑dollar budget and reporting to the founding team.

This senior role requires hands‑on systems building, vendor management across the U.S. and nearshore/offshore, and a relentless focus on data quality and safety as deployments grow. Expect frequent travel to vendor sites.

Qualifications

• 5+ years scaling high-volume, quality-measured operations teams (hundreds of people).
• Experience managing outsourced vendors and building in-house teams in the US and nearshore/offshore locations.
• Systems builder who will do the job hands-on before delegating to others to achieve scale.
• Detailed understanding of data quality for AI teams.
• Willingness to travel frequently to be onsite with vendors.

Responsibilities

• Lead pilot training and quality assurance programs, including certification and grading systems.
• Forecast pilot demand and manage hiring pipelines to meet deployment ramp while preserving quality.
• Develop processes for deploying pilots with new customers and certify readiness.
• Own vendor management end-to-end, SLAs, quality reviews, and onboarding of new vendors.
• Grow the in-house pilot operations team alongside key vendors as the company scales.
• Collaborate with R&D on the rollout of AI policies and ensure safe, scalable implementation.

Skills

High-volume ops

Quality data practices

Vendor management

Hands-on leadership

Travel readiness

Job description

About Ultra

Ultra builds industrial AI robots that are working in the real world today. Our robots automate mission-critical warehouse labor end-to-end, starting with e-commerce order packaging. We deploy fast, learn from real production data, and iterate aggressively. We already have a quickly growing number of revenue-generating robots operating in U.S. warehouses, and are now scaling towards thousands of deployments over the next few years. Our mission is simple: build the world's most useful and deployable robot.

WARNING:

Robotics is not for the faint of heart. There are no silver bullets here. It is tiresome, unglamorous, and at times brutal work. The only way out is through, and the only way through is treacherous and unknown.

Success will require teamwork

• so we are building a world-class team to tackle some of the most exciting problems out there. We hope you join us.

The role

Teleoperation pilots are foundational to how our business operates — delivering immediate value to customers the moment we deploy, generating the high-quality data that trains our robots, and monitoring our AI policies as they run in the field. Over the next year we'll scale this team from dozens of pilots to hundreds, and we're looking for a Pilot Operations Lead to build and run that organization.

This is a senior role with real ownership. You'll lead a rapidly growing operation with a multi-million-dollar budget, and you'll have the autonomy to shape how it's built — how we hire, train, structure, and hold quality as we scale. You won't be doing it alone: you'll have the backing of the founding team and direct access to the resources you need to move fast.

Success in this role takes a rare blend of technical fluency, operational rigor, and people leadership. We are looking for significant experience in directly transferable roles — the kind of experience you'd find in a co-founder, or senior TPM who has built and scaled a function from the ground up in a data labeling, self-driving, or robotics operation.

What you'll own

• Pilot training and quality assurance. Scale the training program, certification bar, and grading/scoring system for pilots.


• Pilot growth forecasting and hiring. Forecast pilot demand against the robot deployment ramp, and own the hiring/staffing pipeline to stay ahead of it without sacrificing quality.


• Customer deployment readiness. Build the process for bringing up pilots for new customer deployments: work with our deployment team to train and certify pilots ahead of each new deployment.


• Vendor management. Own the external pilot contractor relationships end-to-end - SLAs, quality reviews - and onboard new vendors as we scale and de-risk.


• In-house team. Design and execute the plan to grow our in-house pilot operations team along-side our key vendors.


• AI adoption tracking and quality. Partner with R&D on the rollout of AI policies. Own the roll-out of AI policies on a customer by customer basis without sacrificing quality of performance.

What we're looking for

• 5+ years scaling high-volume, quality-measured operations teams with hundreds of people — robotics fleet ops, data labeling ops, or similar.


• Experience managing outsourced vendors and building in-house teams, both in the US as well as in nearshore/offshore locations (Spanish speaking a plus).


• Systems builder: you aren't afraid to get your hands dirty and do the job yourself before hiring and delegating to someone else to achieve scale.


• Detailed understanding of the importance of data quality for AI teams.


• You are comfortable with frequent travel to be onsite with vendors, especially during critical scale-up periods.

Equal Employment Opportunity Statement

We are an Equal Opportunity Employer. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We are committed to creating a diverse and inclusive environment and encourage applicants from all backgrounds to apply.