Executive Assistant

Who you are

• 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 confidence
• Thrives in a dynamic, high-growth environment where priorities shift and speed matters

What the job involves

• 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
• 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
• 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
• 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
• 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
• 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

Benefits

• Medical, Dental & Vision: Your healthcare will be available from Day 1— giving you immediate peace of mind — with best in class coverage and options.
• Parental Leave: Step away with paid time off to focus on family and life’s newest chapter.
• NYC HQ: Collaborate in our lively New York headquarters, with new office space on the way!
• 401(k) Retirement Savings: Plan ahead with our 401(k) program to grow your future. And starting early 2026, employees will be eligible for a company match!
• Flex Giving: ‍Flex Giving empowers employees to support local nonprofits advancing housing stability in the communities we call home.
• Employee Assistance Fund: ‍Confidential financial support to teammates facing unexpected hardships or emergencies.
• Hybrid Work Policy: Work flexibly from home, with in-person collaboration and events that matter.
• Unlimited PTO + Holidays: Take the time you need— whether that’s a vacation, recharge, or simply a long weekend
• Free Flex Subscription: As a Flex employee, you’ll …