Head of Pilot Operations

Ultra • Brooklyn, OH

108d

About The Position

The Head of Pilot Operations will build and lead the teleoperation pilot organization as it scales from dozens of pilots to hundreds. The role has ownership of a multi-million-dollar budget and the autonomy to shape how the organization hires, trains, structures, and maintains quality as it grows, with support from the founding team and access to needed resources.

The position combines technical fluency, operational rigor, and people leadership. It requires significant experience in directly transferable roles, such as a co-founder or senior technical program manager who has built and scaled a function from the ground up in data labeling, self-driving, or robotics operations.

Requirements

• At least 5 years scaling high-volume, quality-measured operations teams with hundreds of people, such as robotics fleet operations or data labeling operations.
• Experience managing outsourced vendors and building in-house teams in the US and in nearshore or offshore locations.
• Ability to build systems and personally perform the work before hiring and delegating to scale.
• Detailed understanding of the importance of data quality for AI teams.
• Comfort with frequent travel to visit vendors, especially during critical scale-up periods.

Nice To Haves

• Spanish-speaking ability.

Responsibilities

• Scale the pilot training program, certification standards, and grading and scoring system.
• Forecast pilot demand against the robot deployment ramp and own hiring and staffing pipelines while maintaining quality.
• Develop processes for preparing pilots for new customer deployments, working with the deployment team to train and certify pilots before each deployment.
• Manage external pilot contractor relationships end-to-end, including service-level agreements and quality reviews, and onboard new vendors as the organization scales and reduces risk.
• Design and execute the plan to grow the in-house pilot operations team alongside key vendors.
• Partner with R&D on AI policy rollouts and own customer-by-customer deployment of AI policies while maintaining performance quality.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed