Remote Personal Finance Strategist for AI Training

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

Benefits offered by this job

Remote work

Flexible schedule

Payments via PayPal/AirTM

LLM access

Job summary

Outlier is seeking personal finance experts to design realistic financial scenarios, evaluate AI-generated plans, and ensure frontier AI meets high standards of accuracy and sound reasoning — all from a fully remote, flexible schedule. This is a 1099 contract opportunity on the Outlier.ai platform, in collaboration with Scale AI.

We do not offer internships or sponsorship. Ideal qualifications include hands-on professional experience in personal tax, investments, financial planning, estate

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 high standards.

Skills

Personal tax

Investments & retirement

Financial planning

Estate planning

Debt & life events

Equity comp & self-employed finances

Job description

Outlier is seeking personal finance experts to design realistic financial scenarios, evaluate AI-generated plans, and ensure frontier AI meets high standards of accuracy and sound reasoning — all from a fully remote, flexible schedule. This is a 1099 contract opportunity on the Outlier.ai platform, in collaboration with Scale AI.

We do not offer internships or sponsorship. Ideal qualifications include hands-on professional experience in personal tax, investments, financial planning, estate