Executive Assistant, CEO

United States·MiamiFull-timemid

Executive AssistantAdministration & Office Support

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Quick Summary

Overview

Flex is building AI-native financial services for business owners.

Technical Tools

Executive AssistantAdministration & Office Support

Flex is building AI-native financial services for business owners.

We’re re-architecting the entire financial system for entrepreneurs—from the first dollar a business earns to how that value compounds, moves, and is ultimately spent in real life. Banking, credit, payments, personal finance, and financial operations—rebuilt from the ground up as a single, intelligent system. Flex is the full financial home for ambitious owners.

Since launching publicly in September 2023, Flex has scaled from zero to nine-figure annualized revenue, with a clear path to profitability by late 2026. We move fast, ship relentlessly, and operate with extreme ownership.

Our customers are affluent business owners ($3–$200M in revenue)—the backbone of the economy and one of the most underserved segments in finance. They’re stuck with outdated banks and fragmented tools. We’re replacing all of it. The opportunity is massive: a ~$1T+ revenue market hiding in plain sight. Our ambition is to build a $100B+ company by delivering a product that is fundamentally better—not incrementally improved.

Flex has raised $100M+ in equity and $300M+ in debt.

- Mission-critical problems: We build software that directly controls how money moves at scale.

- High bar, low ego: Small teams, exceptional people, real ownership.

- Speed over comfort: We prioritize execution, quality, clarity, and results.

- Enduring impact: What we’re building will define how a generation of owners runs their businesses.

Team & Locations

We hire exceptional people who want to build hard things and see their work matter immediately. Roles are available in: San Francisco, Miami, New York, and fully remote.

Flex Fuels Ambition.

This role keeps the CEO’s day running the way it should — the right meetings in the right order, so the context from his morning carries cleanly into the afternoon. You’ll own his calendar and travel, with the judgment to resequence on the fly when priorities shift, and the discretion to flag what needs his direct attention versus what can wait. Your hours will largely mirror his — when he’s working, you’re reachable.

Own and proactively manage the CEO’s calendar — sequencing and grouping meetings so related context stays together and he’s not constantly switching gears between unrelated conversations
Regularly act as first point of contact, exercising judgment on what is a priority versus what should be delegated, deferred, or declined
Coordinate complex domestic and international travel, often on short notice
Prepare briefing materials, agendas, and follow-ups for board meetings, investor, and leadership meetings
Handle confidential and sensitive information with discretion
Anticipate needs before they’re asked and resolve problems independently

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

Experience supporting a CEO or founder in fintech, banking, or another regulated industry
Experience coordinating directly with boardmembers or investors

Why Join Us

Build something generational — Capture the full lifecycle of money for ambitious business owners.

Work on real money, real risk — Payments, credit, and banking at serious scale.

Solve hard problems — AI, underwriting, compliance, and global finance from first principles.

True ownership — Small teams, high trust, real accountability.

Founder-level exposure — Direct access to leadership, customers, and investors.

High bar, high taste — Move fast without cutting corners.

Elite peers — People here are builders, not tourists.

Real upside — Meaningful equity if you help build something big.

Location & Eligibility

Where is the job

Miami, United States

On-site at the office

Who can apply

About this job

Pay per year: $100,000–$140,000 a year; 33% above the $90,217 median for Executive Assistant jobs on Jobera (453 salaries).
Who can apply: United States
Posted: 26 days ago
Employer: has 32 open jobs on Jobera in 4 countries.