Staff Product Manager

The Role

At Pilot, we're on a mission to grow the small business economy — and we're at an inflection point. AI is fundamentally reshaping what's possible in financial services, and this role sits at the center of that transformation.

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.

Key Responsibilities 

• 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

About You

• 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

Bonus Points

• Experience as a founder or operator running a business yourself
• A background in finance, accounting, or fintech
• Hands-on experience building or deploying AI, agentic, or LLM based products

Why This Role Matters

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.

About Pilot

Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts - which Pilot hires as full-time, U.S.-based employees - who learn the ins-and-outs of their business. Pilot integrates directly with the billing, banking, expense, and payroll systems customers already use. With a special b