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Remote Content Labelling Jobs in Chicago, IL (NOW HIRING)

TSMG

AI/ML Data Contributor

Chicago, IL · Remote

Perform AI/ML-related tasks such as data labeling, annotation, and content evaluation * Participate in remote assignments or attend on-site sessions when required * Follow project guidelines and ...

TSMG

AI/ML Data Contributor

Chicago, IL · Remote

Perform AI/ML-related tasks such as data labeling, annotation, and content evaluation * Participate in remote assignments or attend on-site sessions when required * Follow project guidelines and ...

Vermillio

Product Manager

Chicago, IL · Remote

... AI content protection and licensing platform. You'll be responsible for building complex, data ... This role will report to the Head of Product and is open to being 100% remote. Key Responsibilities ...

Vermillio

Product Manager

Chicago, IL · On-site +1

... AI content protection and licensing platform. You'll be responsible for building complex, data ... This role will report to the Head of Product and is open to being 100% remote. Key Responsibilities ...

Brady

Clinical Workflow Specialist

Chicago, IL · Remote

This is a remote role based in the U.S. Integrating Clinical Excellence Throughout the Sales ... RFP Content Validation: Contribute expert clinical evidence and technical specifications to RFP ...

All JobsContent Labelling JobsRemote Content Labelling JobsRemote Content Labelling Jobs in Chicago, IL

Remote Content Labelling information

See Chicago, IL salary details

$30.4K

$120.1K

$132.9K

How much do remote content labelling jobs pay per year?

As of Aug 12, 2026, the average yearly pay for remote content labelling in Chicago, IL is $120,131.00, according to ZipRecruiter salary data. Most workers in this role earn between $126,700.00 and $131,900.00 per year, depending on experience, location, and employer.

What are some common challenges faced in remote content labelling roles and how can they be managed?

Remote content labellers often encounter challenges such as maintaining focus during repetitive tasks, managing ambiguous guidelines, and ensuring consistent quality across large datasets. To address these, it's helpful to establish a structured daily routine, actively participate in team discussions or feedback sessions, and utilize available resources for clarification on guidelines. Collaborating with team leads and other labellers through chat platforms also helps in resolving uncertainties efficiently and maintaining high accuracy standards.

What are the key skills and qualifications needed to thrive as a remote content labeller, and why are they important?

To thrive as a Remote Content Labeller, you need strong attention to detail, analytical thinking, and familiarity with content guidelines, typically supported by a high school diploma or equivalent. Experience with content management systems, annotation tools, and sometimes specific training on labeling protocols is often required. Excellent communication, time management, and the ability to work independently are valuable soft skills for this role. These skills ensure accurate and consistent labeling, which is critical for training AI systems and maintaining content quality at scale.

What is remote content labelling?

Remote content labelling is the process of identifying, tagging, or classifying various types of digital content—such as images, videos, text, or audio—from a remote location, typically from home. This work is crucial for training machine learning algorithms and improving artificial intelligence systems, as labelled data helps computers understand and process information. Remote content labellers use specific guidelines and tools provided by their employer or client to ensure consistency and accuracy. The job often requires attention to detail, good communication skills, and the ability to follow instructions closely.

What is the difference between Remote Content Labelling vs Remote Data Annotation?

AspectRemote Content LabellingRemote Data Annotation
Primary FocusLabeling and categorizing content such as images, videos, and text for machine learningAdding detailed annotations to data to improve model accuracy, often including bounding boxes, segmentation, or key points
Skills RequiredAttention to detail, understanding of content types, basic data handlingTechnical skills, familiarity with annotation tools, precision in marking data
Work EnvironmentRemote, flexible hours, often part-time or freelanceRemote, similar flexible setup, often within AI or ML projects

Both roles involve working remotely to prepare data for AI models, but Content Labelling primarily involves categorizing content, while Data Annotation requires detailed technical markings. Understanding these differences helps job seekers find the right fit for their skills and career goals.

What are the most commonly searched types of Content Labelling jobs in Chicago, IL? The most popular types of Content Labelling jobs in Chicago, IL are:
What are popular job titles related to Remote Content Labelling jobs in Chicago, IL? For Remote Content Labelling jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote Content Labelling jobs in Chicago, IL look for? The top searched job categories for Remote Content Labelling jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Remote Content Labelling jobs? Cities near Chicago, IL with the most Remote Content Labelling job openings:
Remote Content Labelling jobs near you

Sr. Support Content Strategist (Remote)

Inspira Financial

Oak Brook, IL • Remote

Full-time

Posted 13 days ago

Inspira Financial rating

7.6

Company rating: 7.6 out of 10

Based on 21 frontline employees who took The Breakroom Quiz

Job description

The Sr. Support Content Strategist is responsible for developing, implementing, and maintaining the support content strategy for partner, administrator, and member-facing Help Centers across Inspira's white-label platform. This role leads the creation, governance, optimization, and delivery of self-service support content, ensuring information is accurate, accessible, scalable, and aligned with partner-specific requirements. This position collaborates closely with Support, Implementation, Product, UX Writing, Compliance, and other stakeholders to drive content effectiveness, support successful partner implementations, and improve the overall user experience through data-driven content strategies.


1.Develop, prioritize, and manage the support content backlog across Health Wallet, Health Wallet Manager, and related platforms.

2. Create, maintain, and optimize support content for multiple audiences, including members, organization administrators, and partner administrators.

3. Configure and launch Help Center libraries for new partners by adapting existing content to partner-specific branding, benefit plans, and program requirements.

4. Partner with Implementation teams to support partner onboarding and Help Center deployment activities in alignment with go-live timelines.

5. Develop and maintain content strategies that support white-label, single sign-on (SSO), API, and other platform configurations.

6. Establish and maintain governance standards to ensure content quality, consistency, accuracy, and scalability across multiple Help Center libraries.

7. Collaborate with UX Writers, Product teams, and subject matter experts to develop and update content supporting product enhancements and feature releases.

8. Monitor and analyze Help Center performance metrics, including search activity, self-service utilization, article effectiveness, support trends, and ticket deflection data.

9. Identify content gaps, improvement opportunities, and emerging support needs using customer and operational data.

10. Optimize content discoverability and usability across Help Centers, search functions, and AI-powered support tools.

11. Develop and maintain content standards, taxonomies, workflows, and best practices that support effective knowledge management.

12. Build and maintain collaborative relationships with Support, Implementation, Product, Compliance, Legal, and other stakeholders.

13. Provide guidance and expertise on support content strategy, governance, and knowledge management practices.

14. Perform other duties as assigned within the nature and level of work.

Bachelor's degree in Communications, English, Journalism, Technical Writing, Marketing, Information Science, User Experience, or a related field

Minimum of six (6) years of experience in help center management, knowledge management, content strategy, editorial operations, or technical content development, with atleast two (2) years in a senor or lead role

Experience managing content across multiple audiences, product configurations, brands, or regulatory requirements

Experience developing content governance frameworks, taxonomies, standards, and knowledge management processes

Experience analyzing content performance metrics and using data to drive content strategy and prioritization

Ability to develop scalable content frameworks and governance models across multiple content libraries

Experience writing and managing content for multiple audiences, preferably within a B2B2C environment

Excellent written, verbal, and interpersonal communication skills

Strong editorial judgment and ability to communicate complex topics in clear, user-friendly language

Ability to influence and collaborate effectively with cross-functional stakeholders

Strong project management and organizational skills with the ability to manage multiple priorities simultaneously

Ability to identify process improvements and drive operational consistency across content programs

Experience working in highly regulated industries or environments with compliance review processes preferred

Familiarity with health spending benefits, including HSA, FSA, HRA, LSA, and commuter programs.

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