AI Product Manager

Role Description

As an AI Product Manager at Freehand - Teams for Business Spend Management, you’ll define and deliver the future of autonomous p2p workflows. You will partner with Engineering, Data Science, UX, and go-to-market teams to ship production-grade AI agents that execute and optimize complex spend workflows with precision, reliability, and explainability. You’ll work directly with CXOs at Fortune 100 companies to understand pain points and convert them into product innovations that displace traditional outsourcing, staffing, and SaaS models with intelligent, self-evolving agents. This is a foundational leadership role with scope to define vision, architecture, and roadmap, and execute against it, for one of the most critical domains in enterprise automations, at the cutting edge of generative AI.

What You'll Do

• Own product vision, architecture, and execution for Freehand’s AI Teams for Spend Management across key use cases:
• Invoice validation & matching
• Vendor onboarding & collaboration
• Contract and compliance management
• Dispute resolution
• Cross-border payments & remittance
• Define agent design patterns—multi-capability prompting, tool orchestration, retrieval pipelines, fallback logic, and policy hierarchies—that balance accuracy, reliability, and real-world business context.
• Ensure end-to-end observability, including agent health, performance monitoring, confidence scoring, and auditability of decisions.
• Partner with AI/ML and data engineering teams to build closed-loop training pipelines and evaluation sets that drive continual improvement via human-in-the-loop feedback, signal instrumentation, and structured reasoning.
• Drive high-fidelity UX for AI interactions, enabling explainable, proactive, and intuitive agent experiences across interfaces (UI, email, chat, APIs).
• Lead technical conversations with enterprise architects and strategic conversations with CFOs, CIOs, and Chief Procurement Officers at Fortune 100 companies.
• Author clear, actionable documentation (PRDs, solution briefs, agent blueprints) and deliver compelling product demos to internal and external stakeholders.

Qualifications

• 4–6 years in B2B product management with at least 2 years working on first products.
• Experience launching agentic AI products involving:
• Multi-agent systems with explicit roles & policies mirroring enterprise auth.
• Strong understanding of AI evaluation techniques (factuality, grounding, latency, hallucination minimization) and methods for improving agent accuracy and reliability in production.
• Proven experience working with enterprise-scale data systems — invoice data, procurement records, contract metadata, FX/tax engines — with deep appreciation for governance, sensitivity, and compliance.

Working at Freehand

• Series C, ~100 people across the US and India. Big enough to have infrastructure, small enough that your work is visible.
• We run on five core operating principles; these are not values-on-a-wall, this is the exact philosophy we built our AI agents on:
• Context Before Confidence.
• Decisions, not Recommendations.
• High Agency, High Trust.
• Accountability is the Product.
• The Work That Remains is the Work That Matters.
• Work Anywhere across US & India (we're remote & travel-first). As and when required, for this role, we will also arrange for a fully-paid trip to our HQ in Chennai to meet & interact with cross-functional teams.

Equal Opportunity

Freehand hires on merit — your thinking, your track record, your potential — without regard to race, gender, age, religion, sexual orientation, national origin, disability, or any other protected characteristic. If you meet most of the criteria above but not all of it, apply anyway. We care more about your willingness to learn & take initiative than whether your resume maps perfectly to every line.