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Annotation Engineer Jobs in Chicago, IL (NOW HIRING)

CHI Project Engineer

Merrillville, IN · On-site

$67K - $87K/yr

Project Engineer Environmental Restoration LLC is a provider of cost effective hazardous wastes ... Documentation includes detailed spreadsheets for project tracking, and annotation of site progress ...

Prompt Engineering * AI Output Evaluation * Quality Assurance * Technical Documentation * Technical & Report Writing * Content Review & Editing * Data Annotation * Data Interpretation * Fact Checking

Prompt Engineering * AI Output Evaluation * Quality Assurance * Technical Documentation * Technical & Report Writing * Content Review & Editing * Data Annotation * Data Interpretation * Fact Checking

Prompt Engineering * AI Output Evaluation * Financial Analysis * Technical & Report Writing * Business Communication * Content Review & Editing * Fact Checking * Data Interpretation * Data Annotation

Prompt Engineering * AI Output Evaluation * Quality Assurance * Technical & Report Writing * Business Communication * Content Review & Editing * Data Interpretation * Data Annotation * Fact Checking

Autocad Tutor

Oak Lawn, IL · Remote

$25 - $40/hr

... annotation, and file management. Ability to explain coordinate systems, object properties, viewport configuration, and CAD standards while preparing students for architecture, engineering, interior ...

Autocad Tutor

Buffalo Grove, IL · Remote

$25 - $40/hr

... annotation, and file management. Ability to explain coordinate systems, object properties, viewport configuration, and CAD standards while preparing students for architecture, engineering, interior ...

Autocad Tutor

Lake Forest, IL · Remote

$25 - $40/hr

... annotation, and file management. Ability to explain coordinate systems, object properties, viewport configuration, and CAD standards while preparing students for architecture, engineering, interior ...

Autocad Tutor

Highland Park, IL · Remote

$25 - $40/hr

... annotation, and file management. Ability to explain coordinate systems, object properties, viewport configuration, and CAD standards while preparing students for architecture, engineering, interior ...

Autocad Tutor

Chicago, IL · Remote

$25 - $40/hr

... annotation, and file management. Ability to explain coordinate systems, object properties, viewport configuration, and CAD standards while preparing students for architecture, engineering, interior ...

Autocad Tutor

Des Plaines, IL · Remote

$25 - $40/hr

... annotation, and file management. Ability to explain coordinate systems, object properties, viewport configuration, and CAD standards while preparing students for architecture, engineering, interior ...

Autocad Tutor

Wheaton, IL · Remote

$25 - $40/hr

... annotation, and file management. Ability to explain coordinate systems, object properties, viewport configuration, and CAD standards while preparing students for architecture, engineering, interior ...

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Showing results 1-20

Annotation Engineer information

See Chicago, IL salary details

$31.9K

$98.7K

$131.3K

How much do annotation engineer jobs pay per year?

As of Aug 26, 2026, the average yearly pay for annotation engineer in Chicago, IL is $98,684.00, according to ZipRecruiter salary data. Most workers in this role earn between $83,400.00 and $119,500.00 per year, depending on experience, location, and employer.

What does an annotation engineer do?

An annotation engineer is responsible for labeling and annotating data, such as images, text, or videos, to train machine learning models. They use specialized tools and follow guidelines to ensure data quality and accuracy, often working closely with data scientists and AI developers. This role requires attention to detail and knowledge of data annotation processes and tools.
Infographic showing various Annotation Engineer job openings in Chicago, IL as of August 2026, with employment types broken down into 90% Full Time, 5% Part Time, and 5% Contract. Highlights an 88% Physical, 4% Hybrid, and 8% Remote job distribution, with an average salary of $98,684 per year, or $47.4 per hour.

AI Software Engineer Expert - Remote

Chicago, IL • Remote

$100 - $200/hr

Part-time

Posted 15 days ago


Job description

Job Title: AI Software Engineering Domain Remote

Job Type: Contractor (Part-Time)
Location: Remote

Job Overview

We are seeking experienced AI Software Engineering Domain Experts to contribute their technical expertise to an innovative project focused on improving next-generation AI systems. In this role, you will evaluate, review, and refine AI-generated software engineering content to enhance the quality, accuracy, and reasoning of AI models. No prior AI experience is required—your software engineering expertise is what matters most.

Key Responsibilities
  • Analyze, review, and improve AI-generated software engineering content for technical accuracy and clarity.
  • Create, refine, and evaluate prompts to improve AI-generated technical outputs.
  • Conduct rubric-based evaluations of AI model responses, providing detailed quality feedback.
  • Draft and edit technical documentation, architecture documents, RFCs, design specifications, and engineering proposals.
  • Perform independent research and fact-checking to validate technical information.
  • Interpret and annotate technical data to support AI model training and evaluation.
  • Collaborate remotely with cross-functional teams to deliver high-quality project outcomes.
Required Skills
  • Critical Thinking
  • Analytical Reasoning
  • Quality Assurance
  • Prompt Engineering
  • AI Output Evaluation
  • Technical Documentation
  • Technical & Professional Writing
  • Content Review & Editing
  • Data Annotation
  • Fact Checking
  • Independent Research
  • Business Communication
  • Problem-Solving
  • Attention to Detail
Preferred Qualifications
  • 3+ years of professional experience as a Software Engineer, Senior Software Engineer, Staff Engineer, Technical Lead, Engineering Manager, Solutions Architect, or similar role.
  • Experience authoring or reviewing technical documentation, architecture documents, RFCs, design specifications, engineering proposals, postmortems, technical blogs, or code reviews.
  • Strong critical thinking, analytical reasoning, and structured problem-solving skills.
  • Excellent written communication and technical editing abilities.
  • Experience with AI coding tools or automated documentation tools is a plus but not required.
  • Advanced degree (Master's, MBA, JD, or PhD) or equivalent professional experience is preferred.