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Founder’s Associate, Strategy Team

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Remote from
USA
Salary
USD 200k–200k / yr
Employment
Full Time
Experience
Open level
Published
Apply before
11 Nov 2026
Listing views
107
Application actions
5
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AI Summary

The role, at a glance.

This Founder's Associate will join Flex's newly formed Office of the CEO and work directly on the company’s highest-priority strategic and operational problems. Responsibilities include market and competitive research, financial modeling, messy-data analysis, cross-functional execution, and identifying opportunities without a predefined playbook. The role requires 3–5 years of high-performance experience in investment banking, private equity, consulting, venture capital, or a fast-growing startup, along with advanced Excel and working SQL knowledge. It is a demanding, high-autonomy position based in Miami or New York City, with travel and regular 12-hour days, 5–6 days per week, particularly during the first year.

Role DNA

A quick view of the complexity, pace, ownership and collaboration implied by the job description.

Job Complexity

5/5
EasyHard

Pace & Pressure

5/5
RelaxedFast-paced

Autonomy Level

5/5
GuidedFull ownership

Communication Load

5/5
IndependentCollaborative
AI insightThe position handles CEO-level priorities that are frequently ambiguous, analytically complex, and cross-functional. Sustaining a stated 12-hour-day, 5–6-day workweek while producing decision-grade work creates an exceptionally demanding environment.

Salary analysis

Estimated compensation compared with the broader US market for similar roles.

Estimated job medianHighly competitive
$200,000
US market range$160k–$240k
AI insightThe disclosed starting base salary is $200,000 USD annually, with equity mentioned separately; the ATS compensation record provides a $200,000 yearly amount. For a US-based Founder's Associate/strategic operations role requiring 3–5 years of elite finance, consulting, or startup experience, an estimated base-salary market range is $160,000–$240,000 annually. Total compensation may be higher when equity and any additional incentives are included.

Core skills

Skills and capabilities most closely associated with this opportunity.

Sample interview questions
Describe a time you solved an ambiguous strategic problem without an established process.

I would explain the context, identify how I framed the decision and gathered imperfect data, then describe the analytical approach, stakeholders involved, and measurable outcome. I would emphasize how I created a repeatable process or recommendation while moving quickly.

How would you evaluate whether Flex should pursue a new financial product or customer segment?

I would begin with the customer problem and market size, then assess strategic fit, economics, regulatory and operational requirements, competitive alternatives, and execution capacity. I would build a scenario-based model, identify the key assumptions and risks, and recommend a staged test with clear success metrics.

Tell me about a financial model you built from messy or incomplete data.

I would describe how I defined the business question, reconciled source data, documented assumptions, and built a transparent model with sensitivity analyses. I would also explain how I validated outputs with operators or subject-matter experts and used the result to support a decision.

How do you prioritize when several executives have urgent requests at the same time?

I would clarify the decision required, expected impact, time sensitivity, and consequences of delay for each request. I would communicate tradeoffs explicitly, align on priorities with the CEO or designated decision-maker, and provide concise interim updates while protecting quality on the highest-leverage work.

This role requires a sustained high-intensity pace. How do you maintain quality under pressure?

I use structured workplans, clear decision logs, and frequent checks on assumptions to avoid rework. Under tight deadlines, I focus first on the few analyses that change the decision, communicate risks early, and reserve time for an independent quality review before presenting conclusions.

This analysis is generated from the job description. Salary estimates, role characteristics and sample answers are guidance, not employer-provided facts.
Opportunity details

About this role.

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 is a new program and the chance to be part of the founding team of the Office of the CEO. We’re creating a small team of high-caliber operators working directly for our Founder & CEO on whatever the company’s highest-priorities are. It is not a rotational program or a fixed analyst lane — scope is set by what the company needs solved, not by a job description. You will be the one to help identify what these opportunities are.

What You’ll Do

  • Take on the CEO’s highest-priority problems directly — strategic projects, market research and competitive work, financial analysis, and cross-functional execution, often with no existing playbook

  • Identify problems, develop solutions, and execute them; often working on multiple initiatives

  • Build and own the models and analyses that inform major company decisions

  • Collaborate with and move fluidly across various departments as business priorities shift

  • As the early stages of this team grows, you will help recruit, ramp, and manage the associates who join after you

Requirements

  • 3–5 years in top-tier investment banking (TMT/fintech coverage), private equity, management consulting, late-stage venture capital, or a fast-growing startup

  • A track record of outperformance — clear signals you were trusted with more scope, faster, than your peers

  • Strong quantitative and analytical skills: advanced Excel, working knowledge of SQL, and comfort dissecting messy data and building models from scratch

  • Extreme rigor and comfort operating in ambiguity at speed — priorities here change faster than the plan does

  • Demonstrated ability to sustain a high-intensity pace: this role will regularly require ~12-hour days, 5–6 days a week, especially in year one

  • This role is based in Miami or NYC but will involve travel

Nice to Haves

  • Ideal background in math, physics, or another highly quantitative field

  • Understanding of fintech, banking, or financial infrastructure

Compensation

The starting base salary for this role is $200k+ equity. This is a full-time role with benefits. Final compensation is commensurate with candidate experience, work location, and interview performance.

Additional Information

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.

Apply now >

This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content.

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