Executive Assistant, CEO

Flex•Miami, FL

About The Position

Flex is hiring an Executive Assistant to support the CEO by keeping the CEO’s day organized and ensuring meetings are sequenced to preserve context. The role owns the CEO’s calendar and travel, and requires judgment to adjust plans as priorities change and to distinguish matters needing the CEO’s direct attention from those that can wait. Working hours will largely mirror the CEO’s schedule, with reachability when the CEO is working, including outside standard hours. The Executive Assistant will act as a first point of contact, coordinate complex domestic and international travel, and prepare materials and follow-ups for board, investor, and leadership meetings. The role also requires discretion with confidential information, anticipating needs, and independently resolving problems. The position is full-time, includes benefits, and is based in or requires relocation to Miami. Willingness to travel as needed is required. Compensation is $100,000–$140,000 per year, commensurate with candidate experience, work location, and interview performance.

Requirements

  • At least 5 years of experience as an Executive Assistant supporting a CEO or Founder at a high-growth startup or similarly high-pace environment.
  • Extreme attention to detail and ability to prioritize competing demands in real time.
  • Sound judgment and discretion when handling confidential and sensitive information.
  • Excellent written and verbal communication skills.
  • Comfort with a high-intensity pace and last-minute changes.
  • Availability that tracks the CEO’s schedule; reachability outside standard hours is part of the job, and this is not a fixed 9-to-5 role.
  • Willingness to travel as needed.
  • Based in, or willing to relocate to, Miami.

Nice To Haves

  • Experience supporting a CEO or founder in fintech, banking, or another regulated industry.
  • Experience coordinating directly with board members or investors.

Responsibilities

  • Own and proactively manage the CEO’s calendar, sequencing and grouping meetings to maintain related context and reduce unnecessary switching between topics.
  • Act as a first point of contact and judge what should be prioritized, delegated, deferred, or declined.
  • Coordinate complex domestic and international travel, often on short notice.
  • Prepare briefing materials, agendas, and follow-ups for board, investor, and leadership meetings.
  • Handle confidential and sensitive information with discretion.
  • Anticipate needs and resolve problems independently.

Benefits

  • Benefits are offered.
  • Meaningful equity is described as potential upside for helping build the company.
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