Program Manager, CS Tools & Technology

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 Flex is rewriting the rules of rent payment, and our CS Tools & Technology team is at the center of making that experience seamless for every renter we serve. As a Technical Program Manager on the CS Tools & Technology team, you'll report directly to the Director of CS Tools & Technology and own the systems, programs, and integrations that power Flex's customer support operations — from Zendesk and automation pipelines to custom-built internal tools and cross-functional integrations. This is not a traditional TPM role. While you'll own program delivery, backlog prioritization, and roadmap execution, this role requires deep, hands-on involvement in designing, building, and [... source excerpt omitted ...] ensuring our CS Tools & Technology stack grows with the business. If you thrive at the intersection of strategy, execution, and technical craft, this role was built for you. What You'll Do Own and manage the team's backlog, sprint planning, and prioritization across all active workstreams, driving end-to-end delivery of large-scale initiatives such as tool migrations, live chat, telephony, and internal tooling Translate business needs and operational pain points into clear functional specifications, user stories, and acceptance criteria — then personally configure, integrate, or guide development of those solutions hands-on Lead UAT planning to ensure solutions meet real-wo [... source excerpt omitted ...] ready outputs — roadmaps, status updates, project briefs, and post-implementation reviews — while identifying risks and unblocking dependencies across cross-functional teams What You'll Bring 4–7 years of experience in technical program management, business systems, or support technology with a track record of increasing ownership and end-to-end delivery Proven builder-operator mindset: the ability to own program delivery while also executing hands-on within systems, integrations, and automation logic Deep hands-on experience with Zendesk administration, including workflow design, routing logic, SLA management, and troubleshooting Practical experience with APIs, webhooks,