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Jobs · Administrative · New York

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

Flex · New York, NY · 2 wk ago
Administrative$320k–$400k/yrFull-time

Flex is a growth-stage, NYC-headquartered FinTech company creating the best rent payment experience. We enable users to pay rent throughout the month on a schedule that fits their finances and budget. Our mission is to empower renters with flexibility over their most significant recurring expense.

About the role

The Strategy & Operations team translates company strategy, operating rigor, and ways of working into execution across Flex. As Chief of Staff and VP of Strategy, you will serve as a senior partner to the CEO and COO, owning the central Strategy & Operations (S&O) team, shaping enterprise strategy, refining our operating model, and driving the hardest problems to resolution. This role reports directly to the CEO and sits at the intersection of the Executive Office and the S&O team. It is a hybrid position with on-site expectations of 3 days per week in our New York Headquarters. For candidates outside the NY/NJ/SF area, relocation assistance may be available.

Responsibilities

  • Chief of Staff to the Executive Office
    • Serve as a trusted thought partner and sounding board to the CEO and COO, helping pressure-test decisions and accelerate alignment.
    • Own high-stakes communications: board materials, company-wide messaging, and external engagements, ensuring clarity and quality.
    • Manage the rhythm of the Executive Office: prepare for critical meetings, ensure follow-through on commitments, and prevent stalling on key decisions.
    • Lead special projects for the Executive Office, stepping into high-priority, time-sensitive workstreams requiring senior judgment.
    • Maintain a high bar for the executive team: surface what’s working and what isn’t, deliver honest upward feedback, and foster optimal team performance.
  • Enterprise Strategy & Cross-Functional Initiatives
    • Lead major cross-departmental initiatives end-to-end, from problem definition to outcome delivery.
    • Shape enterprise-level strategy on market expansion, organizational design, and long-range planning.
    • Serve as a trusted advisor to the CEO and COO, driving decisions forward and pushing back when needed.
    • Step in where needed, including board deck preparation, executive communications, or high-priority cross-functional support.
  • Team Standard-Bearer
    • Set and uphold standards of excellence in analytical rigor, communication quality, and operational discipline for the S&O team.
    • Lead recruiting with a clear, consistent bar for talent at every level.
    • Own career development, structured feedback, and coaching for the team.
    • Build the team as a cohesive cohort with shared identity, operating norms, and mutual accountability.

Requirements

  • 15+ years of professional experience spanning management consulting and/or senior Strategy & Operations, Business Operations, or Chief of Staff roles at high-growth companies.
  • A first-principles problem solver: thrive in ambiguous, high-friction environments and build solutions when the path isn’t clear.
  • Resilient and comfortable with ambiguity: structure messy problems, move quickly, and revise as you learn without losing focus.
  • Proven team leadership: built, developed, and scaled high-performing teams with genuine ownership over people’s growth.
  • Exceptional ability to work the system, not just the project: understand organizational dynamics, influence without formal authority, and drive outcomes.
  • Skilled at influencing up: bring critical conversations to leadership, push back when needed, and earn trust through substance.
  • High horsepower, low ego: comfortable rolling up your sleeves on urgent tasks or shaping long-range strategy.
  • Outstanding written and verbal communication: clear in writing, confident in discussions, and able to distill complexity into crisp recommendations.
  • Demonstrated AI fluency: actively leverage AI tools to accelerate analysis, improve workflows, and drive better decisions.
  • Sound commercial judgment: understand business mechanics, spot risks and opportunities quickly, and make decisions that hold up under scrutiny.
  • Strong quantitative reasoning: comfortable with financial modeling or analytical problem-solving to turn complex data into defensible recommendations.
  • Exceptional emotional intelligence: read a room, build trust with executives, and act as both partner and 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.

Pay

Flex uses a market-based approach to pay, with compensation adjusted for geographic location based on a cost of labor index. For Tier 1 (NYC/Bay Area) markets, the base salary range for this role is $320,000–$400,000 USD. Candidates outside these areas will receive a location-adjusted range.

Benefits

  • For full-time U.S. employees:
    • Competitive medical, dental, and vision coverage.
    • 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:
    • Competitive compensation + company equity.
    • Unlimited PTO.

Schedule

This is a hybrid role with on-site expectations of 3 days per week in New York Headquarters.

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