About Freehand
Most AI companies are building tools. We're building the worker.
Freehand's AI agents replace the human decision-making and coordination layer that sits above enterprise software — handling the analysis, negotiation, prioritization, and execution that previously required armies of logisticians / supply chain professionals.
Our customers include Apple, Meta, GE, Pfizer, J&J, Schlumberger, Cardinal Health, and Unilever. They chose us because we have a fundamentally different answer to what enterprise software looks like when AI can do the job.
If you want to work on something that matters, with people who will push you to be sharper than you thought you could be, this is the place.
The Role & The Team
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 eng teams to build closed-loop training pipelines and eval 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.
4–6years 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 FreehandSeries 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. We get in, ask (a ton of) questions, connect the dots ourselves and move fast. No passengers, no hand-holding. The amount of confidence you'll have in Week 1 is directly proportional to the context strive to gain.
Decisions, not Recommendations. Freehand folks decide, they don't present options. You'll have real autonomy, and real accountability to match.
High Agency, High Trust. We won't manage you closely or ask you to escalate every call. Act, share your reasoning, and course-correct when needed. That's the contract.
Accountability is the Product. When something goes wrong — and it will — we name it, learn from it, and move on. No politics, no cover. Just fix it.
The Work That Remains is the Work That Matters. We actively cut low-value work. What lands on your plate is there because it matters — and can only be done by you.
It's a small world. Freehand employees 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.
In addition, we proudly offer the following Benefits to all our full-time employees:
Full Health coverage (accidental, life, vision, dental & health consultations)
Monthly home-internet costs
Flexible working hours
Complimentary food & snacks at the Chennai HQ
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
