Executive Assistant, CEO

Flex•Miami, FL

6d•$100,000 - $140,000

About The Position

Flex is hiring an Executive Assistant to support the CEO by managing the flow of his day, keeping meetings appropriately sequenced and preserving context as priorities shift. The role owns the CEO’s calendar and travel, uses judgment to determine what needs his attention, and serves as a first point of contact. The schedule largely mirrors the CEO’s, with availability and reachability outside standard hours required; this is not a fixed 9-to-5 role. The position is based in Miami, or requires willingness to relocate there, and includes travel as needed. Flex describes itself as building an AI-native private bank for business owners. It is re-architecting financial services—including banking, credit, payments, personal finance, and financial operations—into a single system. The company says it has grown to nine-figure annualized revenue since its public launch in September 2023 and has raised more than $100 million in equity and $300 million in debt. Its roles are available in San Francisco, Miami, New York, and fully remote, although this position specifically requires being based in or relocating to Miami. The role prepares materials and follow-ups for board, investor, and leadership meetings; coordinates complex domestic and international travel, sometimes on short notice; handles confidential information discreetly; and anticipates needs and resolves problems independently. Flex describes the position as full-time with benefits. Compensation is $100,000–$140,000 annually, with final compensation based on experience, work location, and interview performance. The company also cites meaningful equity as potential upside.

Requirements

At least 5 years of experience as an Executive Assistant supporting a CEO or founder at a high-growth startup or similarly fast-paced 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 working at a high-intensity pace and adapting to last-minute changes.
Availability that tracks the CEO’s schedule; reachability outside standard hours is part of the job, and the role is not a fixed 9-to-5.
Willingness to travel as needed.
Based in Miami 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 preserve related context and reduce unnecessary switching between topics.
Act regularly as the first point of contact and decide 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.