Senior EA

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 They’re stuck with outdated banks and fragmented tools.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.

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.

This is not a traditional EA role.

You will act as the CEO and executive team's operating system — owning time, information flow, priorities, and execution across business and personal domains. You are ruthless about leverage, allergic to chaos, and exceptional at anticipating problems before they exist.

If done well, this role 10x’s the company. If done poorly, it doesn’t work at all.

We are looking for someone who has already operated at this level.

You are accountable for outcomes, not tasks.

Own the CEO’s calendar end-to-end with zero tolerance for low-leverage meetings

Actively shape days and weeks based on strategic priorities, energy, and deadlines

Manage relationship's with investors, executives, partners, and in some contexts... friends and family

Prepare daily and weekly briefs: what matters, what’s coming, what can wait

Be the single intake point for inbound: email, text, Slack, WhatsApp, etc

Triage ruthlessly: respond, delegate, escalate, or kill

Track open loops across work and personal life until closed

Ensure follow-ups happen without the CEO needing to remember

Anticipate needs 1–3 steps ahead (travel, meetings, decisions, sensitivities)

Pre-read meetings and surface risks, context, and landmines

Draft emails, messages, and responses in the CEO’s voice

Act as a trusted thought partner, not just an executor

Travel planning across complex, multi-city schedules

Household coordination, logistics, appointments, and life admin

Discretion and emotional intelligence across sensitive relationships

Reduce cognitive load so the CEO can operate at peak performance

This role only works if you are exceptional.

8+ years supporting a Founder, CEO, or ultra-high-performing investor/executive

You’ve operated in high-growth, high-pressure environments

You think in systems, not checklists

You have elite written and verbal communication skills

You are calm under chaos and decisive under ambiguity

You have impeccable judgment and know when to push back

You are deeply discreet and ethically bulletproof

You derive pride from making a company unstoppable

Not a junior EA role

Not a “wait for instructions” role

Not a 9-to-5 mindset

Not a stepping stone unless you are elite at this craft

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.