Remote Personal Finance Strategist for AI Training

ISHE; Northern (KY); Hybrid; USD 83,000 - 124,000; Full time

Benefits offered by this job

Up to $90/hr compensation

Remote work flexibility

LLM access included

Flexible schedule (5–10 hrs/week)

Job summary

Outlier is seeking personal finance experts to design realistic scenarios, evaluate AI-generated plans, and ensure frontier AI meets high standards of accuracy and sound reasoning — all from a fully remote, flexible schedule.

You will work on a freelance contract via the Outlier.ai platform in collaboration with Scale AI, with compensation up to $90/hr and optional incentives. Most experts spend 5-10 hrs/week, with a fully remote setup across the US.

Qualifications

• Personal tax — preparing individual (1040) returns, personal tax planning, capital-gains, self‑employment/quarterly taxes.
• Investments & retirement — advising individuals on portfolios and retirement accounts (asset allocation, rebalancing, 401(k)/IRA/Roth, Social Security).
• Financial planning — comprehensive personal planning (budgeting, cash flow, debt, goals).
• Estate planning (non-attorney) — estate and gift tax, trust administration, beneficiary planning, fiduciary accounting.
• Debt & life events — student loans, mortgage refinance, credit-card payoff, home affordability, 529/college planning.
• Equity comp & self-employed finances — RSUs, stock options, ESPP, or freelancer/self‑employed personal cash‑flow.

Responsibilities

• Design and solve complex, real-world client scenarios to train AI in expert personal financial planning.
• Critique AI-generated deliverables for accuracy and sound reasoning, ensuring every output meets the standards you would hold your own client work to.

Skills

Personal tax

Investments

Financial planning

Estate planning

Debt & life events

Equity comp & self-employed finances

Job description

Outlier is seeking personal finance experts to design realistic scenarios, evaluate AI-generated plans, and ensure frontier AI meets high standards of accuracy and sound reasoning — all from a fully remote, flexible schedule.

You will work on a freelance contract via the Outlier.ai platform in collaboration with Scale AI, with compensation up to $90/hr and optional incentives. Most experts spend 5-10 hrs/week, with a fully remote setup across the US.