Director of Product Management, CS/AI

Flex is a growth-stage, NYC headquartered FinTech company that is creating the best rent payment experience. It’s hard to believe that it’s 2026 and paying rent on time is expensive, inflexible, and difficult. We’re here to change that! Flex enables our users to pay rent throughout the month on a schedule that better fits their finances and budget. Our mission is to empower as many renters as possible with flexibility over their most significant recurring expense. After deliberately keeping a stealth profile as we built up unprecedented investor support and an enthusiastic user base, we are looking for motivated individuals to help us keep our mission growing. Will you be a part of the team? About the role We’re hiring a Director of Product for AI & Agentic Customer Support to own the strategy and outcomes for how Flex resolves customer issues -  automatically, intelligently, and at scale. Customer support at Flex is a multi-channel operation spanning AI voice, AI chat, live chat, email, and live human voice, serving bill payers managing payments, billing changes, onboarding and identity, account issues, and more. With hundreds of human agents and a rapidly growing bill payment base, the mission is to resolve more, faster, and with less friction. This role owns the full agentic stack: the in-app customer experience that routes bill payers to the right channel and drives toward self-resolution; the LLM-native orchestration layer that powers automated resolution; the M