Pilot Operations Lead

Ultra; New York (NY); On-site; USD 120,000 - 180,000; Full time

Job summary

Ultra in New York seeks a Senior Pilot Operations Lead to build and run a scalable teleoperation pilot function. You'll own training, vendor relationships, and customer deployment readiness, with a multi‑million dollar budget and direct access to the founding team.

Success requires experience scaling high‑volume, quality‑measured operations, plus hands‑on systems building and people leadership across US and nearshore/offshore vendors, including travel to sites as needed.

Qualifications

• 5+ years leading large-scale, quality-driven ops teams (hundreds of people).
• Experience managing outsourced vendors and building in-house teams.
• Strong systems builder with hands-on approach to scaling operations.

Responsibilities

• Pilot training and quality assurance. Scale training, certification, and grading for pilots.
• Pilot growth forecasting and hiring. Forecast demand and own staffing pipeline to scale without compromising quality.
• Customer deployment readiness. Build processes to train and certify pilots before deployments.
• Vendor management. Own external pilot contractor relationships, SLAs, and onboarding as we scale.
• In‑house team growth. Plan to grow our in-house pilot ops team alongside key vendors.
• AI adoption tracking and quality. Partner with R&D on rollout of AI policies and ensure quality.

Skills

Scaling operations

Vendor management

People leadership

Data quality

Travel readiness

Job description

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