Staff Product Manager, Pilot

• A proven track record of shipping AI, financial, or data-driven products that have moved meaningful business metrics, not just launched, but delivered
• 7+ years building products, ideally with significant time in B2B and/or data-intensive domains
• Deep familiarity with the agent toolchains, model evaluation frameworks, evaluation/orchestration tools (e.g., Arize, LangChain, Prefect, Airflow)
• Outstanding analytical and problem-solving skills: you can break down complex systems, identify failure modes, and make high-quality decisions with incomplete information
• Exceptional ability to learn complex domains quickly and communicate them simply to customers, executives, and the board

Desirable

• We're looking for a Staff Product Manager to lead Pilot's Agent driven bookkeeping automation platform
• This is one of the highest-impact, highest-visibility roles at Pilot
• The future of our business, and frankly, the future of bookkeeping as an industry, will be shaped by what this team builds
• We're talking about the kind of foundational work that sets a company up for double and triple-digit growth, and positions Pilot as the definitive AI-native back office for small businesses
• The foundation of financial insights is banking data
• This team owns the core automation, including agent pipelines, that ensures bank transaction data is accurate, timely, and actionable
• You'll drive Pilot's AI transformation from the product layer, architecting how we apply agentic workflows to achieve near-fully autonomous bookkeeping, and setting the standard for how great agent driven products get built and shipped
• This is a generalist PM role at its core, but one that requires deep fluency in AI, not just familiarity
• You'll work shoulder-to-shoulder with our engineering and technical teams, speak their language, and make hard technical and product tradeoffs with confidence
• Own and drive Pilot's AI transformation for a critical product area, defining the roadmap for how agent orchestration becomes the engine of automated bookkeeping
• Ship outstanding features to drive Pilot’s product feature set, and be responsible for that product delivering substantial impact for both our customers and our business
• Partner deeply with technical teams software engineers to design, build, and ship AI-powered features at high quality
• Audit and evaluate system system quality: assess product quality, pipeline reliability, output performance, and data fidelity; push the bar on what "production-ready" means
• Set the strategic vision for how agent-native bookkeeping evolves at Pilot, influencing company-level decisions about technology investment, product direction, and competitive positioning
• Talk to customers, understand their pain points, and translate those insights into customer solutions they didn't know were possible
• Make smart prioritization decisions informed by customer feedback, data, and a clear-eyed view of technical feasibility and business impact
• Serve as the internal and external ambassador for your product, keeping leadership, cross-functional partners, and customers excited and aligned on what's being built and why
• Pilot is at a once-in-a-generation moment. AI is enabling us to reimagine what bookkeeping looks like, moving from human-heavy workflows to intelligent automation that gives small business owners real-time, accurate financial clarity with minimal friction
• The PM who leads this area will have direct influence on our growth trajectory, our technical architecture, and our positioning in the market
• This is not a supporting role. It's a defining one, for Pilot, and for the category