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 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

Who You Are

• 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

Compensation

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

Life at Flex

We understand that it takes a diverse team of highly intelligent, curious, determined, empathetic, and self aware people to grow a successful company. Our HQ is located in New York City, but we have employees located throughout the US, Australia, Canada and South America. We are growing quickly, but deliberately, with a focus on building an inclusive culture. Our dynamic team has incredible perspectives to share, just as we know you do, and we take great pride in being an equal opportunity workplace.

Offices

Roles posted in New York, San Francisco, and Salt Lake City are hybrid positions with on-site expectations of 2-3 days per week in our local offices. For candidates outside of these areas, you may be eligible for our relocation assistance program.

Benefits

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