Financial Planning Expert - Remote, Flexible Contract Work

Squillace & Associates, P.C.; Northern (KY); Hybrid; USD 83,000 - 124,000; Full time

Benefits offered by this job

Up to $90/hr pay

Remote work

Flexible schedule

PayPal & AirTM payments

LLM access

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. Your expertise helps shape how advanced AI systems reason, learn, and improve, turning frontier research into AI that performs better in the real world.

This is a 1099 contract opportunity on the Outlier.ai platform, in collaboration with Scale AI.

Qualifications

• Hands-on professional experience serving individual clients in one or more of the listed areas.

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 outputs meet high standards.

Skills

Personal tax

Investments

Financial planning

Estate planning

Debt management

Equity compensation

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. Your expertise helps shape how advanced AI systems reason, learn, and improve, turning frontier research into AI that performs better in the real world.

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.

Compensation & Benefits:

• Earn up to $90/hr, plus additional incentives (rates vary based on expertise and project requirements; paid via PayPal and AirTM)
• Free access to leading LLMs (GPT, Claude, and more) — worth $200+/month, included at no extra cost
• Choose your own schedule — most experts spend 5-10 hrs/week, up to 40 hours
• 100% remote — work from anywhere in the US

This is a 1099 contract opportunity on the Outlier.ai platform, in collaboration with Scale AI. Because this is a freelance opportunity, we do not offer internships, sponsorship, orIdeal Qualifications — hands-on professional experience serving individual clients in one or more of:

• 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.

Currently accepting applicants from the United States. employment.