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Crossing Hurdles

Verified Job SourceRecruitment agency

Connecting ambitious talent with high-growth companies worldwide.

Staffing and Recruiting
201–500 people

About

Crossing Hurdles connects skilled professionals with opportunities across leading AI training platforms and high-growth companies. As global demand for human input in AI development continues to grow, many platforms rely on large networks of capable contributors across technical, analytical, and knowledge-based domains. Crossing Hurdles helps professionals discover and access these opportunities by bringing together information, talent networks, and application pathways related to AI model training, evaluation, and emerging AI-enabled work. Through our growing community of candidates and professionals, we help individuals explore opportunities with global AI platforms that are building and improving next-generation AI systems. These opportunities often span areas such as technical analysis, research, reasoning tasks, and other knowledge-driven work that supports the development of modern AI models. Alongside the AI ecosystem, Crossing Hurdles also works with high-growth companies to support talent discovery across key business functions. We collaborate with founders, leadership teams, and hiring managers to help them connect with capable professionals for full-time roles across both on-site and remote teams. Over the past few quarters, we have partnered with companies including Angel One, Ixigo, Cars24, Veera, ABP Network, Battery Smart, Zavya, and Twin Engineers, supporting hiring initiatives across multiple sectors. Key areas of focus • Opportunities across AI training and evaluation platforms • Technology & Product roles • Growth, Marketing & Sales • Customer Success & Support • Finance & Business Operations By bringing together talent networks, industry insights, and emerging opportunities across AI and high-growth companies, Crossing Hurdles aims to help capable professionals discover meaningful work while supporting organizations in reaching the talent they need to grow.

Open positions

Treasury Analyst | $70/hr Remote

Remote · Canada

Evaluate and test banking, treasury, and cash-management workflows to identify operational strengths and limitations. Provide expert feedback and document findings to refine AI-enabled tool connectivity and workflow logic.

Private Equity & Investment Funds Attorney

Remote · Canada

Review and annotate transactional agreements and provide structured feedback on credit and banking documents. Evaluate legal language to improve AI learning frameworks and draft sample clauses to identify risk areas.

Investment Banking Analyst (M&A) | Remote

Remote · Canada

The role involves sourcing and providing eligible finance transaction documents such as CIMs, SPAs, and board decks. The expert must ensure all materials are compliant, free from proprietary restrictions, and accurately classified with detailed metadata.

Senior AI Trainer – Financial & Investment Analysts | Remote

Remote · Canada

The role involves producing high-difficulty expert tasks and gold-standard solutions within the financial functional area. It also requires reviewing team output, calibrating quality, and escalating complex edge cases to the SME Lead.

Investment Analyst | Remote

Remote · Canada

Develop complex financial models and conduct comprehensive investment analysis to assess business opportunities and risks. Prepare strategic financial reports and monitor market trends to inform capital markets decisions.

Investment Banking Specialist | $65/hr Remote

Remote · Canada

Provide expert insights on investment banking concepts and analyze financial models, pitch books, and valuation reports. Collaborate with AI trainers to refine datasets and ensure industry-standard accuracy in all communications.

Commercial Insurance Underwriter | $70/hr Remote

Remote · Canada

Evaluate complex commercial and specialty risk scenarios in the US insurance market. Analyze and structure coverage for excess and specialty lines, ensuring compliance with industry standards.

Financial Analyst | $25/hr Remote

Remote · Canada

The role involves analyzing financial data and developing financial models to support decision-making. Additionally, the analyst will evaluate financial risks and ensure compliance with regulations.

Financial Analyst | $30/hr Remote

Remote · ["Canada"]

Position: Finance Expert Type: Contract Compensation: $20 - $30/hour Location: Remote Commitment: 10-40 hrs/week Role Responsibilities Submit original financial documents such as reports, investment analyses, and valuation models. Ensure submissions include multimodal content like tables, charts, and data visualizations. Demonstrate expertise in financial analysis, modeling, and reporting in all contributions. Maintain accuracy, proper sourcing, and professional polish in every document. Provide documents ranging from 10 to 100 pages to capture comprehensive reports and focused analyses…

Investment Banking Consultant | $65/hr Remote

Remote · Canada

The role involves providing insights on investment banking concepts and analyzing financial documents. Additionally, the consultant will collaborate with AI trainers to refine datasets and assess complex financial scenarios.

Underwriter | Remote

Remote · Canada

The underwriter will review and assess AI-generated outputs related to insurance claims and provide expert feedback to improve AI models. They will also identify errors and compliance issues based on their professional experience.

Senior Underwriter / Risk Specialist | Remote

Remote · Canada

The role involves translating insurance workflows into tasks for AI systems and evaluating AI outputs for accuracy and relevance. Additionally, the position requires identifying gaps in model performance and providing structured feedback.

Treasury Analyst | Remote

Remote · Canada

Evaluate AI-generated outputs for accuracy and reasoning quality in accounting scenarios. Provide structured feedback to improve AI model performance.

Financial Analyst | $40/hr Remote

Remote · Canada

The role involves critically reviewing and analyzing finance-related interview content for accuracy and applicability. Additionally, the analyst will assess AI-generated materials and collaborate with internal teams to enhance content effectiveness.

Senior Financial Analyst | Remote

On-site · Canada

Role: Corporate Finance Specialists (FP&A / Financial Modeling / Valuation) Engagement Type: Freelance / 1099 Contractor, Remote Compensation: $100–$125 per hour Commitment: Minimum 10+ hours/week (Ideally 15–20 hours, depends upon interest and availability) Start: Immediate | 24-hour fast-track onboarding required Key Responsibilities Translate real-world corporate finance workflows into structured tasks for AI systems Evaluate AI-generated outputs for financial accuracy, logical reasoning, and business relevance Work on use cases including financial modeling, budgeting, forecasting, v…