Head of Pilot Operations
AI summary of the role
Ultra is scaling its teleoperation pilot team from dozens to hundreds over the next year.
What you’ll do
- Scale pilot training program, certification bar, and grading/scoring system.
- Forecast pilot demand against robot deployment ramp and own hiring/staffing pipeline.
- Build process for training and certifying pilots ahead of new customer deployments.
- Manage external pilot contractor relationships end-to-end, including SLAs and quality reviews.
What you’ll bring
- 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 in US and nearshore/offshore locations.
- Systems builder who can do the job hands-on before delegating.
- Detailed understanding of data quality importance for AI teams.
Technologies
AI · robotics · teleoperation · data labeling · autonomous vehicles · warehouse automation
Source and classification
Internal deployment & tooling · Evidence for this classification:
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
More from the 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 mul [... source excerpt omitted ...] 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 [... source excerpt omitted ...] 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 s
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