Capital Allocation Specialist - Remote AI Evaluation Freelance Role
About the Role
Crossing Hurdles is partnering with a US-based AI frontier lab to source senior corporate finance professionals for remote, freelance AI evaluation work. This is not a traditional finance role. Our client is building and refining AI systems that need to think, reason, and respond like real practitioners - and they need Capital Allocation Specialists who can tell the difference between a model that gets it right and one that gets it wrong.

What You Will Do

Review and evaluate AI-generated responses related to capital allocation, investment decisions, and financial planning

Rate outputs for accuracy, depth, and real-world applicability

Write and refine prompts that challenge AI models on complex finance scenarios

Provide expert feedback that directly shapes how AI tools reason through capital structure, ROI analysis, and resource prioritization

Flag errors, inconsistencies, or reasoning gaps from a practitioner's perspective

Domain Focus

Capital allocation strategy and portfolio prioritization

Investment analysis and return modeling

Corporate resource planning and budgeting

Financial risk assessment tied to capital decisions

Variance analysis and performance reporting against allocated capital





What We Are Looking For

5+ years of experience in corporate finance, FP&A;, strategic finance, or capital planning

Prior roles such as Capital Allocation Specialist, FP&A; Manager, Strategic Finance Lead, or Senior FP&A; Analyst

CFA designation or MBA in Finance strongly preferred

Strong command of financial modeling, NPV, IRR, and scenario analysis

Ability to evaluate reasoning quality, not just surface-level accuracy

Excellent written communication and analytical thinking

Work Style and Expectations
This is a remote, asynchronous-friendly engagement. You set your own schedule within weekly hour commitments. Work is conducted independently, and strong performers are regularly considered for expanded retainer arrangements.

Compensation

Rate : $100-125/hr (USD)

Payment : Via Deel, fortnightly

Commitment : 15-20+ hours/week (minimum 10+ hours/week)

You May Be a Good Fit If
You have hands‑on experience making or advising on real capital allocation decisions, you can spot when a financial model or recommendation misses the mark, and you are looking for flexible, high-value work from home that puts your expertise to use in a meaningful way.

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📌 Capital Allocation Specialist | Remote (Manitoba)
🏢 Crossing Hurdles
📍 Manitoba