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Pilot is a hybrid software/service platform that handles financial back office operations (bookkeeping, tax, CFO services) for tech startups and SMBs, serving thousands of customers with a 150+ person Customer Operations team.
This is an individual contributor role reporting to the Head of Business Operations. You'll sit at the center of work planning, allocation, forecasting, and increasingly, AI-assisted automation across the organization. The role owns multiple interconnected systems: work orchestration (routing work efficiently as volume and capacity shift), KPI reporting (real-time business performance dashboards for leadership), resource forecasting (staffing and capacity models), billing operations (accuracy and reconciliation at scale), and process automation.
Key responsibilities include:
- Building and maintaining work orchestration systems that allocate work across teams as demand and capacity change
- Creating real-time KPI reporting that gives leadership clear visibility into performance and flags anomalies early
- Developing forecasting models that project staffing needs and translate them into actionable recommendations
- Owning billing sheet accuracy, reconciliation, and QA processes
- Identifying and building automation solutions using Excel/Sheets scripting, SQL, and AI tools to replace manual and repetitive work
- Leading process improvements end-to-end, including change management for adoption
You'll work directly with senior leadership and cross-functional partners. This is not a "build one dashboard and maintain it" role—it's for someone who wants to continuously evolve systems as the business and work itself change.
Required: 3–5 years in business operations, analytics, or finance (ideally startup/tech environment) with a track record of building and running systems. Expert-level Excel/Sheets (formulas, modeling, scripting), working SQL proficiency, and familiarity with analytics tools (e.g., Looker). Comfort with AI tools like Claude. Strong detail orientation, systems thinking, demonstrated project leadership on operational system builds, and ability to communicate technical work clearly to senior leadership.
Hybrid role based in San Francisco or Nashville office.
