Executive Assistant

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?

About The Role Flex is seeking a proactive, detail-oriented Executive Administrator to join our growing executive support function and directly support a pod of senior leaders. This role sits at the center of how Flex’s executive team operates — protecting time, enabling focus, and ensuring the coordination that powers our leadership runs smoothly and intentionally.

As Flex scales rapidly, this is not a traditional administrative role. Executive Administrators at Flex are expected to be genuine partners to the leaders they support — understanding priorities, exercising judgment, and operating as part of a coordinated team rather than optimizing in isolation. You’ll work closely with the Manager, Executive Administration and peer EAs to ensure cross-executive scheduling reflects org-wide priorities, not just individual availability.

This is a hybrid position with minimum on-site expectations of 3 days per week in our New York Headquarters. For candidates outside of the NY/NJ area, you may be eligible for our relocation assistance program.

What You’ll Do Calendar Management & Prioritization

• Own end-to-end calendar management for a pod of 2–3 senior executives, including scheduling, rescheduling, and proactive prioritization
• Manage competing demands with judgment — pushing back, protecting focus time, and escalating tradeoffs when appropriate
• Coordinate cross-executive scheduling in partnership with peer EAs, with an org-wide lens on how time is being used
• Maintain meeting hygiene standards: appropriate durations, clear agendas, and timely prep materials

Travel & Logistics

• Book and manage business travel for supported executives, including flights, hotels, ground transportation, and itineraries
• Anticipate logistics needs and proactively solve for complications before they become problems
• Support coordination of leadership offsites, board meetings, and all-hands logistics as needed

Meeting Preparation & Follow-Through

• Prepare briefing materials, agendas, and context documents ahead of key meetings
• Leverage AI transcription and action-tracking tools to capture outputs and ensure follow-through from executive meetings
• Help executives stay on top of commitments and action items that emerge from high-priority meetings

AI-Assisted Workflows

• Use AI scheduling and productivity tools as a core part of your workflow — for calendar analysis, meeting prep, transcription, and logistics research
• Contribute to the team’s evolving AI tooling practices by sharing what’s working and helping refine approaches over time

Team Coordination & Operations

• Participate in weekly EA team alignment and contribute to a coordinated, high-trust team dynamic
• Partner with the Manager, Executive Administration to flag coordination issues, capacity concerns, or process gaps
• Contribute to playbooks and documentation that help the function scale consistently

Key Qualifications

• 3+ years of experience in executive administration, executive support, or a similar role in a fast-paced environment
• Experience directly supporting senior or C-suite executives with complex, high-volume calendars
• Strong organizational skills and exceptional attention to detail — you follow through, every time
• Sound judgment and discretion; able to handle sensitive information and navigate ambiguous situations with maturity
• Comfortable using AI tools in your day-to-day work, with a genuine interest in how they can create leverage (scheduling assistants, transcription tools, meeting prep, etc.)
• Collaborative team player who understands that great executive support is a team sport, not a solo act
• Clear, professional communicator — written and verbal — who can represent executives with con…