Strategic Finance Lead - AI Evaluation Contractor
Placed by Crossing Hurdles | Remote | $100-125/hr USD

About the Role
Crossing Hurdles is partnering with a leading US-based AI frontier lab to source senior Corporate Finance professionals for a remote freelance engagement. The company is building evaluation frameworks to train and improve AI systems, and they need practitioners with real-world strategic finance experience to assess model outputs, identify reasoning errors, and help define what accurate, high‑quality financial analysis looks like. This is not a traditional finance role. It is expert consulting work where your domain knowledge directly shapes AI performance.

What You Will Do

Review and evaluate AI‑generated financial analyses, forecasts, and strategic recommendations

Identify errors in logic, methodology, and financial reasoning

Provide structured written feedback that improves model accuracy and reliability

Compare competing AI outputs and assess which best reflects sound strategic finance practice, and contribute to evaluation rubrics and quality benchmarks for corporate finance tasks

Domain Focus

FP&A; and long‑range financial planning

Capital allocation and investment prioritization

Business unit performance analysis and variance reporting





Scenario modeling and sensitivity analysis

Strategic finance advisory and executive‑level decision support

What We Are Looking For

5 or more years of experience in strategic finance, FP&A;, or corporate finance

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

CFA designation or MBA with a Finance concentration preferred

Solid command of financial modeling, forecasting methodology, and business case development

Ability to articulate why an analysis is correct or flawed in clear, written form

Comfortable working independently in a remote, async‑first environment

Work Style and Expectations
This is a remote, flexible engagement. You set your own schedule within the week. The company values consistency and quality over rigid hours, but expects contributors to show up reliably and meet weekly output goals. Strong performers are considered for expanded scopes and longer‑term retainer arrangements.

Compensation
Rate : $100-125/hr (USD)

Payment : Via Deel, fortnightly

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

#J-18808-Ljbffr

📌 Strategic Finance Lead | Remote (Manitoba)
🏢 Crossing Hurdles
📍 Manitoba