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Grading Contractor In Jobs in Chicago, IL (NOW HIRING)

YO AI Labs

In-House Counsel - Remote

Chicago, IL · Remote

$90 - $150/hr

Contractor Location: Remote Job Overview We are seeking experienced In-House Counsels with a strong ... Develop objective evaluation frameworks, rubrics, and grading criteria for assessing AI performance ...

micro1 AI

In-house Counsel

Aurora, IL · Remote

$90 - $130/hr

Contractor Location: Remote Job Summary: We are seeking seasoned in-house transactional attorneys ... Create objective evaluation frameworks and grading criteria to assess AI performance on contract ...

micro1 AI

In-house Counsel

Elgin, IL · Remote

$90 - $130/hr

Contractor Location: Remote Job Summary: We are seeking seasoned in-house transactional attorneys ... Create objective evaluation frameworks and grading criteria to assess AI performance on contract ...

micro1 AI

In-house Counsel

Chicago, IL · Remote

$90 - $130/hr

Contractor Location: Remote Job Summary: We are seeking seasoned in-house transactional attorneys ... Create objective evaluation frameworks and grading criteria to assess AI performance on contract ...

micro1 AI

In-house Counsel

Naperville, IL · Remote

$90 - $130/hr

Contractor Location: Remote Job Summary: We are seeking seasoned in-house transactional attorneys ... Create objective evaluation frameworks and grading criteria to assess AI performance on contract ...

micro1 AI

In-house Counsel

Joliet, IL · Remote

$90 - $130/hr

Contractor Location: Remote Job Summary: We are seeking seasoned in-house transactional attorneys ... Create objective evaluation frameworks and grading criteria to assess AI performance on contract ...

YO AI Labs

Clinicia Expert - Remote

Chicago, IL · Remote

$150 - $200/hr

Contractor Location: Remote Job Overview We are seeking experienced Clinicians specializing in ... Assess dose escalation strategies, dose-limiting toxicities, adverse event grading, attribution ...

YO AI Labs

Oncology Expert - Remote

Chicago, IL · Remote

$150 - $200/hr

Contractor Location: Remote Job Overview We are seeking experienced Clinicians specializing in ... Assess dose escalation strategies, dose-limiting toxicities, adverse event grading, attribution ...

YO AI Labs

Oncology Expert - Remote

Chicago, IL · Remote

$150 - $200/hr

Contractor Location: Remote Job Overview We are seeking experienced Clinicians specializing in ... Assess dose escalation strategies, dose-limiting toxicities, adverse event grading, attribution ...

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Infographic showing various Grading Contractor In job openings in Chicago, IL as of August 2026, with employment types broken down into 70% Full Time, 9% Part Time, and 21% Contract. Highlights an 88% Physical, 1% Hybrid, and 11% Remote job distribution.

In-House Counsel - Remote

YO AI Labs

Chicago, IL • Remote

$90 - $150/hr

Part-time

Posted 9 days ago

Job description

Job Title: In-House Counsel – Technology Transactions

Job Type: Contractor
Location: Remote

Job Overview

We are seeking experienced In-House Counsels with a strong background in technology transactions to contribute to a project focused on advancing next-generation legal AI systems. This part-time opportunity is designed for experienced lawyers who have substantial expertise in contract drafting, review, negotiation, and redlining, particularly within the technology sector.

In this role, you will evaluate and contribute to contract redlining and negotiation workflows used to train and assess advanced AI models. Your legal judgment will help improve how AI systems identify contractual risks, interpret complex provisions, and produce precise, commercially appropriate legal analysis.

No prior AI experience is required—your legal expertise, transactional judgment, and technology-sector experience are what matter most.

Key Responsibilities
  • Perform simulated contract negotiations and redlining exercises involving technology transactions.
  • Draft, review, analyze, and revise commercial agreements, including MSAs, NDAs, DPAs, and related technology contracts.
  • Evaluate AI-generated responses to contract scenarios for legal accuracy, commercial reasonableness, risk identification, and drafting quality.
  • Provide clear, actionable feedback to improve AI-generated contract analysis and redlining outputs.
  • Develop objective evaluation frameworks, rubrics, and grading criteria for assessing AI performance on contract drafting, review, and negotiation tasks.
  • Identify contractual risks, ambiguities, unfavorable provisions, and negotiation opportunities.
  • Assess whether proposed revisions appropriately reflect business objectives and acceptable legal risk.
  • Collaborate with product, legal, and research teams to refine datasets, evaluation guidelines, and best practices for AI-driven contract review.
  • Contribute practical insights into how experienced in-house counsel approach contract negotiations and risk allocation.
Required Skills
  • Contract Drafting
  • Technology Transactions
  • Contract Negotiation
  • Contract Redlining
  • Contract Review
  • Legal Risk Analysis
  • Commercial Contracting
  • Structured Legal Feedback
  • Legal Technology
Required Qualifications
  • Minimum 3 years of in-house legal experience with a focus on technology transactions.
  • Demonstrated experience negotiating and redlining MSAs, NDAs, DPAs, and other commercial technology agreements.
  • Strong understanding of technology contracting, contractual risk allocation, and commercial negotiation strategies.
  • Exceptional written and verbal communication skills with meticulous attention to detail.
  • Strong analytical and critical-thinking abilities.
  • Ability to translate legal expertise and professional judgment into clear, actionable feedback.
  • Ability to evaluate contractual language objectively and consistently.
  • Demonstrated interest in innovation at the intersection of law and technology.
  • Experience collaborating with cross-functional or multidisciplinary teams in fast-paced environments.
Preferred Qualifications
  • Prior experience working with AI, legal technology, contract lifecycle management, or AI training and evaluation initiatives.
  • Experience developing legal review guidelines, playbooks, negotiation frameworks, or quality standards.
  • Familiarity with AI-assisted contract review and analysis tools.
  • Experience working with technology companies or high-growth environments.
  • Strong interest in the development and application of AI within the legal profession.
Why Join?
  • Work at the intersection of law, technology, and artificial intelligence.
  • Help shape how advanced AI systems understand and evaluate real-world contracts.
  • Apply your transactional legal expertise to high-impact AI research and development.
  • Contribute to the development of tools designed to enhance legal analysis, contract review, and professional legal judgment.