Overview
Strategic Finance Lead | Remote Jobs in Canada at Crossing Hurdles
Title: Strategic Finance Lead | Remote
Company: Crossing Hurdles
Location: Canada
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 – 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 – Strong 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) – Type: Long-term engagement, retainer opportunities for strong performers You May Be a Good Fit If You have spent years doing the kind of strategic financial analysis that most AI tools still get wrong. You can spot a flawed assumption, a misapplied model, or a weak recommendation quickly, and you can explain why. You want flexible, well-compensated work that puts your expertise to use in a field that actually needs it. To apply, send your resume to Crossing Hurdles for review. No lengthy forms. No multiple interview rounds. Qualified candidates move to a short onboarding call and can be up and running within 24 hours.
