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Remote Maintenance Trainer Jobs in Chicago, IL (NOW HIRING)

... training project focused on improving Dutch-language understanding and generation. In this role ... Collaborate with quality assurance leads to maintain consistency and accuracy in evaluations.

Remote Engaging lawyers to contribute their subject-matter expertise in support of a customer ... Apply meticulous attention to detail to maintain exceptionally high standards in all submissions.

Regional Trainer (Midwest)

Aurora, IL · On-site +1

$95K - $110K/yr

The Regional Trainer works independently in the field while maintaining regular communication with ... Remote, home-office-based position. * Preferred residence in the Chicago, Illinois metropolitan ...

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Remote - Entry Level Client Sales Representative (Training Provided) 100% Remote | U.S. Applicants ... Document client interactions and maintain organized records * Participate in virtual training ...

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Sales Manager Remote

Chicago, IL · Remote

$80K - $120K/yr

Conduct regular one-on-one meetings, team meetings, and training sessions to maintain product ... What we offer: * 100% remote work with a flexible schedule. * Competitive compensation structure ...

Creole Remote Interpreter

Chicago, IL · Remote

$22.75 - $29.75/hr

Maintain strict confidentiality and adhere to all applicable professional ethics, standards, and ... Certification, training, or other relevant qualifications in interpreting preferred. * Ability to ...

Creole Remote Interpreter

Chicago, IL · Remote

$22.50 - $29.75/hr

Maintain strict confidentiality and adhere to all applicable professional ethics, standards, and ... Certification, training, or other relevant qualifications in interpreting preferred. * Ability to ...

Apply relevant style guides and maintain consistency in tone, terminology, punctuation ... Develop AI training content that improves model accuracy, fluency, and contextual understanding.

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Apply relevant style guides and maintain consistency in tone, terminology, punctuation ... Develop AI training content that improves model accuracy, fluency, and contextual understanding.

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Remote Maintenance Trainer information

See Chicago, IL salary details

$14

$25

$37

How much do remote maintenance trainer jobs pay per hour?

As of Aug 26, 2026, the average hourly pay for remote maintenance trainer in Chicago, IL is $25.48, according to ZipRecruiter salary data. Most workers in this role earn between $19.33 and $27.26 per hour, depending on experience, location, and employer.

What is a remote maintenance trainer?

A Remote Maintenance Trainer is a professional who provides training and support to maintenance personnel through virtual or online platforms. Their main responsibility is to teach technicians how to operate, troubleshoot, and repair equipment without being physically present onsite. This role often involves creating training materials, conducting live remote sessions, and utilizing various digital tools to simulate real-world scenarios. Remote Maintenance Trainers are essential for organizations with distributed teams or those adopting remote support technologies.

How does a remote maintenance trainer typically collaborate with on-site technicians to ensure effective training and support?

A Remote Maintenance Trainer frequently works closely with on-site technicians through video calls, screen sharing, and digital training platforms to deliver instructions and provide real-time troubleshooting guidance. Collaboration often includes creating customized training materials, conducting virtual workshops, and offering follow-up support to address specific challenges. Clear communication and adaptability are key, as trainers must tailor their approach to different skill levels and respond promptly to technical questions. This role usually involves regular coordination with maintenance supervisors and other trainers to ensure consistent knowledge transfer and continuous improvement.

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

To thrive as a Remote Maintenance Trainer, you need a solid background in mechanical or electrical maintenance, experience in training delivery, and often a relevant technical certification or degree. Familiarity with virtual training platforms, remote diagnostic tools, and learning management systems (LMS) is typically required. Excellent communication, patience, and adaptability help trainers engage learners and address diverse needs in a remote environment. These skills are crucial to effectively transferring technical knowledge and ensuring maintenance teams perform safely and efficiently from a distance.

What is the difference between Remote Maintenance Trainer vs Maintenance Technician?

AspectRemote Maintenance TrainerMaintenance Technician
CertificationsOften requires technical certifications, training credentialsRequires technical or trade certifications, depending on specialization
Work EnvironmentPrimarily remote, online training sessions, virtual supportOn-site or field work, hands-on equipment maintenance
Employer & Industry UsageUsed in manufacturing, industrial, and technical training companiesCommon in manufacturing, facilities management, and industrial sectors

The main difference is that Remote Maintenance Trainers focus on delivering training and support remotely, often via online platforms, while Maintenance Technicians perform hands-on repairs and maintenance on equipment on-site. Both roles require technical knowledge, but their work environments and daily tasks differ significantly.

What are the most commonly searched types of Maintenance Trainer jobs in Chicago, IL?

The most popular types of Maintenance Trainer jobs in Chicago, IL are:

What are popular job titles related to Remote Maintenance Trainer jobs in Chicago, IL?

For Remote Maintenance Trainer jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Remote Maintenance Trainer jobs in Chicago, IL look for?

The top searched job categories for Remote Maintenance Trainer jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Remote Maintenance Trainer jobs?

Cities near Chicago, IL with the most Remote Maintenance Trainer job openings:

Remote Accounting & Tax Expert, AI Trainer

Accounting Fly

Chicago, IL • Remote

$75 - $125/hr

Contractor

Posted yesterday

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Job description

Job Title: Remote Accounting & Tax Experts, AI Trainer
Job ID: 1061580
Date Posted: August 19, 2026
Employment Type: Contract, 12-week, 30-40+ hrs/week
Hiring Company (Organization): Confidential
Location: US Remote (Telecommute)
Applicants must be located in the United States.
Hourly Rate: $75 to $125 per hour (USD/1099)
DOE and suitability for the work.
Job Description: Remote Accounting & Tax Experts, AI Trainer / Domain Expert
Our client is seeking accounting, tax, and finance professionals for a 12-week AI training sprint. Contributors act as subject matter experts to evaluate, annotate, and improve AI-generated responses on accounting, tax, and financial reporting topics, and design realistic professional tasks (scenarios, supporting files, grading rubrics) used to train and test AI systems. This is not a traditional accounting role — no client work, no month-end close, no deadlines — but a structured, flexible engagement putting accounting knowledge toward AI development.
Responsibilities
  • Review and evaluate AI-generated accounting responses for accuracy, clarity, and professional appropriateness
  • Annotate and rank model outputs to guide AI training
  • Write expert-level answers to accounting questions as training examples
  • Flag errors, misconceptions, or ambiguous outputs and provide corrective guidance
  • Design and build realistic task scenarios from professional experience, including prompts, supporting files, and grading rubrics
  • Run tasks against AI models and iterate based on expert reviewer feedback
  • Follow detailed written instructions precisely (formatting, upload requirements, etc.)
  • Maintain consistent quality and throughput for the full sprint
Qualifications
  • Available for 30–40 hours/week for the full 12-week engagement
  • 7+ years demonstrated accounting experience (public accounting, corporate finance or tax, public accounting tax, advisory, M&A, or similar)
  • CPA or EA preferred but not required
  • Strong written communication skills
  • Comfortable working independently in a remote, self-directed setting
  • Careful reader of instructions; receptive to feedback and revisions
  • Baseline tech literacy (cloud tools, browser profiles, desktop app installs, file conversion/zipping)
  • Based in the United States
  • General understanding of LLMs/AI landscape
Compensation & Terms
  • Paid on a regular cadence; contract position
  • Fully remote (work from anywhere in the US)
  • Paid skills assessment required (3–4 hours, $240 flat rate; no AI/LLM assistance permitted)
  • No obligation to continue after the sprint; flexible project-based work often available afterward

Accountingfly logo

About Accountingfly

Sourced by ZipRecruiter

In 2016, Accountingfly determined that fully-remote recruiting was the future of accounting staffing, offering huge benefits for employers, job-seekers, and our own business. We decided to focus our recruiting business on those companies offering only remote work opportunities—and it was the best decision we ever made. While our competitors struggle to adapt to the remote world, we lean on years of experience to provide unmatched remote accounting recruitment expertise. We’ve seen and done it all, successfully filling a wide variety of remote roles and making career dreams come true for talent at every level.

Industry

Accounting services

Company size

1 - 10 Employees

Headquarters location

Pensacola, FL, US

Year founded

2011

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