AI Banking Quality Architect & Evaluation Lead

Obsidian; New York (NY); On-site; USD 120,000 - 180,000; Full time

Job summary

Obsidian is seeking an experienced investment banking professional to design task-specific grading criteria and to score AI-generated and human work samples with detailed written justifications. You will define what excellent banking work looks like and apply evidence-based, defensible scoring across models, memos, and pitch materials.

The role emphasizes strong analytical skills, rigorous valuation modeling, and exceptional written communication, with a preference for experience in AI training

Qualifications

• 2+ years of professional investment banking experience (associate level or above).
• Experience at leading global investment banks or elite advisory boutiques in M&A, coverage, or capital markets.
• Deep fluency in three-statement and transaction modeling (DCF, LBO, comps, merger math) and formatting of bank-quality work.
• Exceptionally strong written communication, with the ability to explain exactly why a piece of work meets or disagrees with the bar.
• Detail-oriented, consistent, and comfortable with peer review calibration.
• Prior experience with AI training, evaluation, or human-data projects is a strong plus.

Responsibilities

• Design precise, task-specific grading criteria for real-world banking deliverables (financial models, valuation analyses, pitch decks and CIMs, deal memos, board and committee materials).
• Score AI-generated and human work samples against those criteria, with detailed written justifications for every score.
• Apply consistent, evidence-based judgment so that scores are reproducible and defensible.
• Incorporate structured feedback from senior reviewers and iterate quickly on your work.

Skills

Investment banking experience

M&A / advisory experience

Financial modeling (DCF, LBO)

Valuation judgment

Strong written communication

AI training / data projects

Job description

Obsidian is seeking an experienced investment banking professional to design task-specific grading criteria and to score AI-generated and human work samples with detailed written justifications. You will define what excellent banking work looks like and apply evidence-based, defensible scoring across models, memos, and pitch materials.

The role emphasizes strong analytical skills, rigorous valuation modeling, and exceptional written communication, with a preference for experience in AI training