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Chief of Staff (Executive Office) and VP of Strategy & Operations

New York, New York, United States

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 is the "API" through which company strategy, operating rigor, and ways of working are translated into execution across Flex. As Chief of Staff and VP of Strategy, you will serve as a senior partner to the CEO and CBO, owning the central Strategy & Operations (S&O) team, shaping enterprise strategy, refining our operating model, and driving the hardest problems in the company to resolution.

This role reports directly to the CEO and sits at the intersection of the Executive Office and the S&O team. It requires someone who can work the system, not just the project, and who is willing to force the conversations that need to happen, even when that's uncomfortable.

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/SF area, you may be eligible for our relocation assistance program.

What You'll Do

  1. Chief of Staff to the Executive Office The Executive Office sets the pace and tone for how Flex operates. Your job is to make it run at its best: decisions made with clarity and speed, communications that reflect the quality of the thinking behind them, and the CEO and CBO free to focus on what only they can do. This means:
    • Serving as a trusted thought partner and sounding board to both executives, helping pressure-test decisions before they're made and accelerating alignment when speed matters
    • Owning the highest-stakes communications: board materials, company-wide messaging, and external engagements, ensuring every artifact reflects the quality and clarity of their thinking
    • Managing the rhythm of the Executive Office: preparing for critical meetings, ensuring follow-through on key commitments, and keeping the most important decisions from stalling
    • Leading special projects on behalf of the Executive Office, stepping into high-priority, time-sensitive workstreams that require senior judgment and a trusted hand
    • Holding a high bar for the quality of the top team: proactively surfacing what's working and what isn't, delivering honest upward feedback, and creating the conditions for the executive team to operate at its best
  1. Enterprise Strategy & Cross-Functional Initiatives You will personally own the highest-stakes strategic work at Flex, the questions and initiatives that don't fit neatly inside any one division or function. This includes:
    • Leading major cross-departmental initiatives end-to-end, from problem definition through outcome delivery
    • Shaping enterprise-level strategy on market expansion, organizational design, and long-range planning
    • Serving as a trusted advisor to the CEO and CBO with the credibility to drive decisions forward and push back when needed
    • Stepping in where needed, whether that's board deck preparation, executive communications, or high-priority cross-functional support
  1. Team Standard-Bearer You will own the health, performance, and trajectory of the S&O team, a small, high-powered cohort operating across Flex's most critical domains. This means:
    • Setting and upholding standards of excellence in analytical rigor, communication quality, and operational discipline
    • Leading recruiting with a clear, consistent bar for what great looks like at every level
    • Owning career development, structured feedback, and coaching
    • Building the team as a true cohort with shared identity, operating norms, and mutual accountability

What You'll Bring

  • 15+ years of professional experience with a track record spanning management consulting and/or senior S&O, Biz Ops, or Chief of Staff roles at high-growth companies
  • A first-principles problem solver: when the map runs out, you build a new one. You don't need a clean brief to do exceptional work, and you've been recognized for figuring it out in ambiguous, high-friction environments
  • Resilient and comfortable with ambiguity: you structure messy problems, move quickly, and revise as you learn, without losing your footing
  • Proven team leadership: you've built, developed, and scaled high-performing teams, and take genuine ownership over the growth of the people around you
  • Exceptional ability to work the system, not just the project: you understand organizational dynamics, know how to move people, and can make things happen without formal authority
  • Skilled at influencing up: you bring the right conversations to leadership, push back when needed, and earn trust through substance, not title
  • High horsepower, low ego: you're as comfortable rolling up your sleeves on an urgent deliverable as you are shaping a long-range strategy
  • Outstanding written and verbal communication: clear in writing, confident in the room, and able to translate complexity into crisp recommendations and decisions
  • Demonstrated AI fluency: you actively leverage AI tools to accelerate analysis, improve team workflows, and drive better decisions, and you set the standard for how your team uses them
  • Sound commercial judgment: you understand how businesses work, spot risk and opportunity quickly, and make decisions that hold up under scrutiny
  • Strong quantitative reasoning: whether through financial modeling or analytical problem solving, you're comfortable turning complex data into clear, defensible recommendations
  • Exceptional emotional intelligence: you know how to read a room, build trust with executives, and show up as both a partner and a coach (even with the CEO)
  • NYC-based and available to work from Flex's Union Square office 3+ days per week

Nice to Have

  • Experience in fintech, consumer lending, or payments
  • Familiarity with the operating rhythms of a late-stage growth company

The compensation range for this role will be commensurate with the candidate's experience and Flex's internal leveling guidelines and benchmarks. For working locations in NY/NJ/CA, the base salary pay range will be $264,000-330,000.

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 
  • Flex Cares Program: Non-profit company match + pet adoption coverage
  • Free Flex subscription

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

  • Competitive compensation + company equity
  • Unlimited PTO

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