Executive Assistant, CEO

Flex is building the AI-native private bank 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 They’re stuck with outdated banks and fragmented tools.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.

About the Role

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.

What You'll Do

• 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

Requirements

• 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

Nice to Haves

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

$100,000 - $140,000 a year

This is a full-time role with benefits. Final compensation is commensurate with candidate experience, work location, and interview performance.

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.