Chief of Staff to the GM of Housing

New York, NY

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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?

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 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.

* 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

* 8+ years of professional experience, ideally including time in management consulting and/or in a high-growth start-up within a Strategy, Business Operations, or Chief of Staff function * Entrepreneurial mindset, energized by the ambiguity and pace of 0-to-1 building * Exceptional conceptual thinker who can move fluidly from strategy to execution and make amorphous problems tractable (“fog sculpting”) * Highly collaborative operator with strong interpersonal skills, able to drive alignment and outcomes through influence rather than authority * Thrives in fast-paced, dynamic environments and maintains composure amid competing priorities * Strong bias for action, paired with obsessive attention to detail and a high bar for work quality * Excellent written and verbal communicator, skilled at distilling complexity into clear, concise narratives and executive-ready materials * Exceptionally quantitative, combining advanced financial modeling skills with fluency in quantitative analysis, budgeting, and forecasting

A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:

* Alcohol or other substance use disorder (not currently using drugs illegally) * Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS * Blind or low vision * Cancer (past or present) * Cardiovascular or heart disease * Celiac disease * Cerebral palsy * Deaf or serious difficulty hearing * Diabetes * Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders * Epilepsy or other seizure disorder * Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome * Intellectual or developmental disability * Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD * Missing limbs or partially missing limbs * Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports * Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS) * Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities * Partial or complete paralysis (any cause) * Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema * Short stature (dwarfism) * Traumatic brain injury

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Flex takes a market-based approach to pay, ensuring compensation is commensurate with a candidate's experience and our internal leveling guidelines. For candidates located in our Tier 1 (NYC/Bay Area) markets, the base salary pay range for this role is below. Flex utilizes a geographic pay differential based on a cost of labor index. If you are located outside of the cities listed below, your starting pay will be adjusted to align with the market conditions of your specific geographic zone. Please speak with your recruiter for additional information regarding the specific range for your location.

Tier 1 (NYC/Bay Area)

$216,000 - $270,000 USD

For full-time U.S. employees we offer:

* Competitive medical, dental, and vision * Company equity * 401(k) plan with company match  * Unlimited paid time off + 13 company paid holidays * Parental leave  * Free Flex subscription

For full-time non-U.S. employees, we offer:

* Competitive compensation + company equity * Unlimited PTO