Chief of Staff to the GM of Housing

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 The Strategy & Operations team serves as the “API” through which company strategy, operating rigor, and ways of working are translated into execution across Flex. As a Chief of Staff to the GM of Housing, you will operate as a trusted thought partner and execution owner for the division’s most critical initiatives. Embedded within the Housing division, you will help define and operationalize strategic priorities, operating cadence, and success metrics. You will support the GM and functional leaders in translating high-level goals into executable plans, while personally owning large, high-impact initiatives from initial strategy through execution and delivery of measurable outcomes. This is an exceptional opportunity for a high-ownership, entrepreneurial operator who thrives in ambiguity, can influence without authority, and is equally comfortable setting strategy and rolling up their sleeves to deliver results. You will report to the Head of Strategy & Operations for Housing and work in close partnership with the GM of Housing, with frequent exposure to the executive team. This is a hybrid position with on-site expectations of 3 days per week in our New York Headquarters. For candidates outside of the NY/NJ area, you may be eligible for our relocation assistance program. What You’ll Do Partner closely with the GM of Housing and functional leaders to define divisional priorities, roadmaps, and operating plans, ensuring alignment with company-level strategy Translate divisional goals into a clear operating system that enables strong cross-functional coordination and execution Own and drive end-to-end strategic initiatives for the Housing division, from problem definition and strategy development through execution and delivery of outcomes Distill progress into executive-facing monthly memos and facilitate review meetings that drive the right strategic conversations and decisions Communicate effectively with senior stakeholders, navigating complex problem sets with clarity and agility Operate at top-decile levels of speed and productivity, dealing constructively with pressure, debate, and competing priorities Continuously improve processes, streamline collaboration, and proactively identify opportunities to optimize how the division operates