Head of Operations Systems & AI Automation

Pilot; San Francisco (CA); On-site; USD 120,000 - 190,000; Full time

Benefits offered by this job

Flexible vacation policy

Observed federal holidays

Parental leave – 100% pay for 12 weeks

401(k) plan

Development opportunities

Job summary

Pilot is seeking a data-driven operations professional to own work orchestration, forecasting, and KPI reporting across the organization. You will build and maintain models that route work efficiently as demand and capacity change, and you will implement automation and AI-driven improvements to reduce manual work.

You will work directly with senior leadership to translate insights into strategic recommendations, ensuring billing accuracy and real-time performance visibility across teams.

Qualifications

• 3–5 years in business operations, analytics or finance, with a track record of building and running a system.

Responsibilities

• Own work orchestration systems and models that route work as volume, capacity, and service lines change.
• Build and maintain KPI reporting giving leadership a real-time view of performance.
• Develop forecasting models for staffing and capacity; translate forecasts into actionable recommendations.
• Own billing sheet accuracy and QA to keep processes scalable and error-free.
• Identify and build automation or AI-driven solutions to replace manual work.
• Lead process improvements across planning, allocation, forecasting, and billing.

Skills

Data fluency

Excel/Sheets expert

SQL

Looker/Analytics tools

AI tooling (Claude, etc.)

Attention to detail

Billing/forecasting

Tools

Excel/Sheets scripting

SQL

Looker

AI tooling

Job description

Pilot is seeking a data-driven operations professional to own work orchestration, forecasting, and KPI reporting across the organization. You will build and maintain models that route work efficiently as demand and capacity change, and you will implement automation and AI-driven improvements to reduce manual work.

You will work directly with senior leadership to translate insights into strategic recommendations, ensuring billing accuracy and real-time performance visibility across teams.