Head of Operations & Business Management

Pilot is moving fast toward agentic, AI-assisted operations, and this person will build and own the systems, models, and reporting that make that shift possible: work orchestration, KPI reporting, resource forecasting, and billing

It’s for someone who wants to keep building better systems as the work itself changes

The role requires real fluency with data and automation tools (Excel/Sheets at an expert level, plus a builder’s instinct for where AI and scripts can replace manual work), sharp attention to detail, and good judgment about what results imply for our strategy and performance

Build and maintain reporting that gives leadership a clear, accurate, real-time view of business performance. Know the data well enough to catch anomalies before they become someone else’s problem

Build and maintain forecasting models that project staffing and capacity needs against demand. Billing Operations: Own billing sheet accuracy and process, including the reconciliation and QA that keeps them error-free at scale

Build these solutions directly rather than just recommending them, using tools like Excel/Sheets scripting, SQL, and emerging AI tooling

Identify and implement improvements to the processes, workflows, and systems this role owns, so accuracy and efficiency improve as the business changes. When an improvement requires cross-functional buildout, lead it end to end, including the change management to get it adopted

Benefits Flexible vacation/time-off policy

All federal holidays are observed

Seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox)

Wellness benefits such as Modern Health, Headscape, One Medical, Aaptiv and Rightway

Project Leadership: Demonstrated experience leading the build or overhaul of an operational system, including the change management needed to get a team to adopt it

Experience: 3-5 years in business operations, analytics, or finance, ideally in a start-up or technology-forward environment, with a track record of actually building and running a system. Experience owning forecasting, billing, or resource-planning is a strong plus

Strong verbal and written communication skills, with the ability to work directly with senior leadership and translate technical or data-heavy work into clear recommendations

Systems Thinking: Able to see how planning, allocation, forecasting, and billing connect, and to design solutions that account for the whole picture rather than one piece of it

Expert-level Excel/Sheets (formulas, modeling, automation/scripting), plus working proficiency in SQL and analytics tools (e.g., Looker).