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

Chief Of Staff And VP Of StrategyFlex is a growth-stage, NYC headquartered FinTech company that is building the payment layer for life's essential bills, giving households one place to see, split, and pay their bills around how they live and get paid. By offering greater choice over how and when payments are made and allowing eligible on time payments to help build a positive credit history, Flex puts households back in control of their cash flow.That work brings together people with different perspectives who challenge the status quo and take ownership of solving difficult problems. For you, that means doing the best work of your career next to people who make you better, and together bringing ideas to life that make a real impact for the people we serve.About The RoleThe 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 COO, 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 Do1. 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 COO 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 mattersOwning the highest-stakes communications: board materials, company-wide messaging, and external engagements, ensuring every artifact reflects the quality and clarity of their thinkingManaging the rhythm of the Executive Office: preparing for critical meetings, ensuring follow-through on key commitments, and keeping the most important decisions from stallingLeading special projects on behalf of the Executive Office, stepping into high-priority, time-sensitive workstreams that require senior judgment and a trusted handHolding 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 best2. 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 deliveryShaping enterprise-level strategy on market expansion, organizational design, and long-range planningServing as a trusted advisor to the CEO and COO with the credibility to drive decisions forward and push back when neededStepping in where needed, whether that's board deck preparation, executive communications, or high-priority cross-functional support3. 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 disciplineLeading recruiting with a clear, consistent bar for what great looks like at every levelOwning career development, structured feedback, and coachingBuilding the team as a true cohort with shared identity, operating norms, and mutual accountabilityWhat You'll Bring15+ 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 companiesA 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 environmentsResilient and comfortable with ambiguity: you structure messy problems, move quickly, and revise as you learn, without losing your footingProven team leadership: you've built, developed, and scaled high-performing teams, and take genuine ownership over the growth of the people around youExceptional 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 authoritySkilled at influencing up: you bring the right conversations to leadership, push back when needed, and earn trust through substance, not titleHigh horsepower, low ego: you're as comfortable rolling up your sleeves on an urgent deliverable as you are shaping a long-range strategyOutstanding written and verbal communication: clear in writing, confident in the room, and able to translate complexity into crisp recommendations and decisionsDemonstrated 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 themSound commercial judgment: you understand how businesses work, spot risk and opportunity quickly, and make decisions that hold up under scrutinyStrong quantitative reasoning: whether through financial modeling or analytical problem solving, you're comfortable turning complex data into clear, defensible recommendationsExceptional 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 weekNice To HaveExperience in fintech, consumer lending, or paymentsFamiliarity with the operating rhythms of a late-stage growth companyCompensationFlex 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)$320,000 —$400,000 USDLife At FlexWe 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.OfficesRoles 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.BenefitsView our benefits and more at getflex.com/careers.