The Flex

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

New York, NY · Exec · Full-time

Sponsorship not specified$320k-$400kDetected 5 days ago

Financial ModelingLeadershipCommunicationProblem SolvingMentoring

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.
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.

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
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
Building the team as a true cohort with shared identity, operating norms, and mutual accountability
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
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
We are growing quickly, but deliberately, with a focus on building an inclusive culture.
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.

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
High horsepower, low ego: you're as comfortable rolling up your sleeves on an urgent deliverable as you are shaping a long-range strategy

Experience in fintech, consumer lending, or payments
Familiarity with the operating rhythms of a late-stage growth company
Flex takes a market-based approach to pay, ensuring compensation is commensurate with a candidate's experience and our internal leveling guidelines.
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.
Tier 1 (NYC/Bay Area)

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.
$320,000 - $400,000 USD

board materials, company-wide messaging, and external engagements, ensuring every artifact reflects the quality and clarity of their thinking
For full-time U.S. employees we offer:
For full-time non-U.S. employees, we offer:

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.
equal opportunity workplace.

This listing is sourced directly from The Flex's careers page and normalized into a canonical job model.