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

<div class="content-intro"><p>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?</p></div><h3><strong>About the Role</strong></h3> <p>The Strategy &amp; 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 &amp; Operations (S&amp;O) team, shaping enterprise strategy, refining our operating model, and driving the hardest problems in the company to resolution.</p> <p>This role reports directly to the CEO and sits at the intersection of the Executive Office and the S&amp;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.</p> <p>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.</p> <h3><strong>What You'll Do</strong></h3> <p><strong>1. Chief of Staff to the Executive Office </strong>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:</p> <ul> <li>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</li> <li>Owning the highest-stakes communications: board materials, company-wide messaging, and external engagements, ensuring every artifact reflects the quality and clarity of their thinking</li> <li>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</li> <li>Leading special projects on behalf of the Executive Office, stepping into high-priori