Job Description
Finance Expert, AI Trainer (Remote, Flexible Hours)100% Remote | Work When You Want | Part-Time or Full-Time | Freelance Contract | $40 to $125 per hour
Fully remote. Work when you want. Get paid for what you already know. Applying takes just a few minutes with your resume.
We are partnering with DataAnnotation to find experienced finance professionals to work as remote AI trainers and evaluate how frontier AI models handle real finance work: valuation and modeling, credit analysis, investment memos, budgeting and variance analysis, and treasury and risk decisions. You bring the judgment you have built defending a model to an investment committee or explaining a variance to a CFO. This is project-based, 100% remote work you do from home on your own schedule, alongside a current job, including evenings and weekends.
Already have a DataAnnotation account? This opportunity runs through our partnership with DataAnnotation. If you have already taken a DataAnnotation starter assessment, you are not eligible to apply through this posting. If you created an account but never took the assessment, you can still apply.
What the Work Involves - Design realistic tasks from your own work, such as a three-statement or DCF model with a valuation summary, a credit memo and covenant analysis, an IC memo, a budget versus actual analysis or a hedging proposal
- Author the supporting files a professional would use: financial statements, models, data extracts, term sheets, board or IC materials
- Run those tasks through frontier AI models and grade the model, memo, analysis or deck they produce
- Compare two model outputs on the same task and document where each fell short
- Write grading rubrics covering the right assumptions, calculations, risks and recommendation
- Flag concrete failures: broken model logic, unsupported assumptions, misread financials, unit and scaling errors, missed risks
Areas of ExpertiseYou need depth in at least one of these, plus enough working knowledge of the others to judge work in adjacent areas:
- Equity or fixed income research
- Portfolio management or trading
- Corporate finance and FP&A
- Credit analysis and underwriting
- Investment banking, M&A or corporate development
- Treasury and liquidity
- Market, credit or liquidity risk
- Wealth management, insurance or actuarial
Who This Is For - 2+ years hands-on in corporate or investment finance
- Degree in finance, economics, business or a quantitative field
- You build and audit models yourself (three-statement, DCF, comps, credit or budget models), not only consume their outputs
- CFA, CPA, FRM or securities licenses welcome but not required
- Mid to late career professionals, including those who are recently retired, are a strong fit
- Hands-on practitioner: you currently do, or recently did, the work yourself as an individual contributor, not solely as a manager
- Strong written English; you can explain clearly why a result is wrong, not only that it is
- Familiar with AI tools such as Claude or ChatGPT, with the judgment to tell a well-reasoned answer from a plausible-sounding wrong one
- Comfortable working independently, following detailed written instructions and incorporating feedback
Pay, Hours and Location - Pay: $40 to $125 per hour, depending on project and expertise. Paid via PayPal on a regular schedule. You are paid for every step you complete
- Hours: Work whenever it suits you, including evenings and weekends. Minimum 10 hours per week with no maximum; full-time hours are available. Multi-day task timers let you spread work across days
- Location: 100% remote, work from home. Must be based in the United States, Canada, or the UK
- Tools: Access to the AI models you will evaluate is provided; no personal subscription needed
How to Apply - Apply here with your resume. It takes just a few minutes, and there are no interviews
- We review your background against the role
- If it's a fit, we send you a link to take DataAnnotation's skills assessment. It's unpaid, takes about 1 to 2+ hours and tests domain judgment and careful reading. The assessment must be entirely your own work; AI-assisted submissions are detected and rejected
- If you pass, you complete onboarding and a short training project, then propose and build tasks from your own professional experience, with expert review and written feedback at each stage
Crucial Recruiting and Sidebar Talent are working together on this search in partnership with DataAnnotation via Navaday.
Job Tags
Hourly pay, Full time, Contract work, Part time, Freelance, Remote work, Work from home, 10 hours per week, Flexible hours, Afternoon shift