Head of AI Operations & Service Delivery

About Subject

Subject is one of the fastest-growing education technology companies in the country, helping more than 1,000 schools deliver flexible, accredited learning to students nationwide. We're backed by Owl Ventures and Kleiner Perkins. Recognized for our growth and innovation:

• TIME's Top EdTech Companies (2026)
• Linked In Top Startups (2025)
• Forbes 30 Under 30 (Co-Founder & CEO Mike Vilardo)
• 135K+ subscribers on You Tube

Subject sits at the intersection of two of the most consequential shifts in education: AI, and the growing demand for flexible learning paths for students who don't fit the traditional classroom model. Subject isn't a commodity courseware vendor. It's an AI-powered K-12 curriculum company serving markets where the stakes for students are high and the need for better outcomes is urgent.

We're growing fast and building out both our Los Angeles headquarters and our Austin office.

The Role

We're hiring a sharp, systems-minded Head of AI Operations & Service Delivery to help scale the engine behind Subject's Customer & Operations team. Working alongside the Head of Customer Success, and reporting into the COO, you'll own the people, processes, and systems across our three operational functions: technical operations (implementation & integrations), our growing services portfolio, and customer support / operations.

You will also use AI to raise the quality, consistency, and efficiency of both our internal operations and our partner-facing support, and be a champion of AI adoption & usage across the company.

This is a senior leadership role: management of 8-12 Operations FTEs across all three teams, paired with hands-on IC work. You're not afraid to roll up your sleeves and ship alongside the team while building the systems that let everything scale. It's full-time, onsite in LA M–F (we maintain a highly collaborative in-office culture), so we're only considering candidates in LA or willing to relocate.

Compensation is highly competitive, commensurate with experience, a mix of base salary + variable tied to company performance + equity.

What You'll Do

• Manage the Operations team and functions; talent, process optimization, documentation, and systems. You drive strategy, execution, and hiring.
• Explore, map, and implement AI tools and LLMs that drive automation and scalability across every Ops function.
• Optimize implementation, integration, and onboarding workflows for Subject's largest districts alongside the Head of Customer Success.
• Lead the Support team behind our Academy and self-service materials - driving support automation so end-users can self-solve.
• Take over management of our highest value services offerings, starting with Teacher of Record programming (more details to be shared in conversations with Subject)
• Own high-value work that supports upsell, cross-sell, and account growth: usage and performance analysis, data reporting, customer-facing training and sales materials, and direct problem-solving with customers.

Who You Are

• 8+ years of relevant experience in operations, product operations, technical support, or customer service - ideally scaling operational systems in a startup.
• Hands-on experience implementing AI tools / LLMs to automate real workflows.
• Exceptional written and verbal communication.
• A player-coach who can both manage people and do the work.
• A self-starter comfortable working independently who also raises a hand when stuck.
• Passionate about education and Subject's mission.
• LA-based or willing to relocate; onsite M–F.

Nice to Have

• Experience managing both FTEs and contractors.
• Familiarity with implementation complex solutions for enterprise-level customers
• Early or mid-stage startup experience (Seed - Series C).
• A background outside edtech, large media/entertainment, or FAANG-scale companies.