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

Flex•New York, NY

1d•$320,000 - $400,000•Hybrid

About The Position

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.

Requirements

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 Haves

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

Responsibilities

Serve 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.
Own the highest-stakes communications: board materials, company-wide messaging, and external engagements, ensuring every artifact reflects the quality and clarity of their thinking.
Manage the rhythm of the Executive Office: preparing for critical meetings, ensuring follow-through on key commitments, and keeping the most important decisions from stalling.
Lead special projects on behalf of the Executive Office, stepping into high-priority, time-sensitive workstreams that require senior judgment and a trusted hand.
Hold 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.
Lead major cross-departmental initiatives end-to-end, from problem definition through outcome delivery.
Shape enterprise-level strategy on market expansion, organizational design, and long-range planning.
Serve as a trusted advisor to the CEO and CBO with the credibility to drive decisions forward and push back when needed.
Step in where needed, whether that's board deck preparation, executive communications, or high-priority cross-functional support.
Set and uphold standards of excellence in analytical rigor, communication quality, and operational discipline.
Lead recruiting with a clear, consistent bar for what great looks like at every level.
Own career development, structured feedback, and coaching.
Build the team as a true cohort with shared identity, operating norms, and mutual accountability.