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Chatgpt Trainer Jobs in Wisconsin (NOW HIRING)

Hanson Dodge

Senior Digital Strategist

Milwaukee, WI · On-site

... Overviews, ChatGPT, Gemini, Perplexity, and other emerging answer engines while aligning with ... Professional development and training opportunities * Exposure to cutting-edge AI search and ...

H&R Block

Tax Associate

Racine, WI · On-site

$54K - $73K/yr

With training and support from day one, you'll work directly with clients to gather information ... Comfort using digital tools and systems included AI based tools like Copilot and ChatGPT * High ...

H&R Block

Tax Associate

Eagle River, WI · On-site

$56K - $75K/yr

With training and support from day one, you'll work directly with clients to gather information ... Comfort using digital tools and systems included AI based tools like Copilot and ChatGPT * High ...

H&R Block

Tax Associate

Brodhead, WI · On-site

$56K - $75K/yr

With training and support from day one, you'll work directly with clients to gather information ... Comfort using digital tools and systems included AI based tools like Copilot and ChatGPT * High ...

H&R Block

Tax Associate

Mayville, WI · On-site

$60K - $80K/yr

With training and support from day one, you'll work directly with clients to gather information ... Comfort using digital tools and systems included AI based tools like Copilot and ChatGPT * High ...

H&R Block

Tax Associate

Stanley, WI · On-site

$61K - $82K/yr

With training and support from day one, you'll work directly with clients to gather information ... Comfort using digital tools and systems included AI based tools like Copilot and ChatGPT * High ...

H&R Block

Tax Associate

Black River Falls, WI · On-site

$55K - $74K/yr

With training and support from day one, you'll work directly with clients to gather information ... Comfort using digital tools and systems included AI based tools like Copilot and ChatGPT * High ...

H&R Block

Tax Associate

Milwaukee, WI · On-site

$57K - $76K/yr

With training and support from day one, you'll work directly with clients to gather information ... Comfort using digital tools and systems included AI based tools like Copilot and ChatGPT * High ...

H&R Block

Tax Associate

West Allis, WI · On-site

$57K - $76K/yr

With training and support from day one, you'll work directly with clients to gather information ... Comfort using digital tools and systems included AI based tools like Copilot and ChatGPT * High ...

H&R Block

Tax Associate

Whitewater, WI · On-site

$57K - $76K/yr

With training and support from day one, you'll work directly with clients to gather information ... Comfort using digital tools and systems included AI based tools like Copilot and ChatGPT * High ...

H&R Block

Tax Associate

Milwaukee, WI · On-site

$57K - $76K/yr

With training and support from day one, you'll work directly with clients to gather information ... Comfort using digital tools and systems included AI based tools like Copilot and ChatGPT * High ...

H&R Block

Tax Associate

Platteville, WI · On-site

$57K - $76K/yr

With training and support from day one, you'll work directly with clients to gather information ... Comfort using digital tools and systems included AI based tools like Copilot and ChatGPT * High ...

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All JobsChatgpt Trainer JobsChatgpt Trainer Jobs in Wisconsin

Chatgpt Trainer information

What is a ChatGPT trainer?

A ChatGPT Trainer is a professional who helps improve and guide the development of AI language models like ChatGPT. Their responsibilities often include annotating data, designing training prompts, reviewing AI responses, and providing feedback to ensure the model generates accurate, safe, and helpful outputs. They may also work on identifying biases, refining conversation flows, and contributing to the overall user experience of AI chatbots. ChatGPT Trainers typically have strong communication and analytical skills, and sometimes a background in linguistics, technology, or education.

What are the key skills and qualifications needed to thrive as a ChatGPT trainer?

To thrive as a ChatGPT Trainer, you need a solid background in linguistics, data annotation, and familiarity with AI language models, often supported by a degree in computer science, linguistics, or a related field. Experience with labeling tools, prompt engineering, and content management systems is typically required. Attention to detail, critical thinking, and strong written communication are vital soft skills for ensuring high-quality data and effective collaboration. These skills and qualifications are crucial for developing accurate, unbiased AI models that deliver useful and ethical responses.

What are the main challenges a ChatGPT trainer faces when curating and evaluating training data?

As a ChatGPT Trainer, one of the primary challenges is ensuring that training data is both diverse and representative of real-world user interactions while maintaining high standards for accuracy and appropriateness. Trainers must carefully balance including varied topics with filtering out biased or sensitive content. Additionally, it can be demanding to keep up with evolving language patterns and user expectations to continually improve model performance. Close collaboration with data scientists, developers, and content moderators is essential to address these challenges effectively.

What is the difference between Chatgpt Trainer vs AI Content Writer?

AspectChatgpt TrainerAI Content Writer
Required SkillsPrompt engineering, AI model understanding, data annotationContent creation, SEO, writing skills
Work EnvironmentAI labs, tech companies, remoteMarketing agencies, media companies, freelance
Industry UsageAI development, machine learning projectsDigital marketing, blogging, publishing

While both roles involve working with AI, a Chatgpt Trainer focuses on training and refining AI language models through prompt engineering and data annotation. An AI Content Writer primarily creates written content optimized for digital platforms. The roles overlap in AI understanding but differ in their core tasks and industry applications.

How do you become a Chatgpt trainer?

To become a ChatGPT trainer, individuals typically need strong skills in natural language processing, machine learning, and data annotation. Gaining experience with AI models, understanding prompt engineering, and familiarity with relevant tools like Python and AI platforms are also important; some roles may require a background in linguistics or computer science.

What are popular job titles related to Chatgpt Trainer jobs in Wisconsin?

For Chatgpt Trainer jobs in Wisconsin, the most frequently searched job titles are:

What job categories do people searching Chatgpt Trainer jobs in Wisconsin look for?

The top searched job categories for Chatgpt Trainer jobs in Wisconsin are:

What cities in Wisconsin are hiring for Chatgpt Trainer jobs?

Cities in Wisconsin with the most Chatgpt Trainer job openings:

Chatgpt Trainer jobs near you
Infographic showing various Chatgpt Trainer job openings in Wisconsin as of August 2026, with employment types broken down into 9% Internship, 74% Full Time, and 17% Part Time. Highlights an 90% In-person, and 10% Remote job distribution.

Training Lead - Guidewire

Markel International

Milwaukee, WI • Hybrid

$88K - $110K/yr

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 19 days ago

Job description

What part will you play? If you're looking for a place where you can make a meaningful difference, you've found it.

The work we do at Markel gives people the confidence to move forward and seize opportunities, and you'll find your fit amongst our global community of optimists and problem-solvers. We're always pushing each other to go further because we believe that when we realize our potential, we can help others reach theirs. Join us and play your part in something special! Markel is seeking a Training Lead - Guidewire to lead training design, development, and delivery across the Guidewire portfolio for the United States and Bermuda. This role is responsible for ensuring employees have the knowledge, skills, and confidence needed to successfully adopt new Guidewire processes and technologies.
The ideal candidate is an experienced instructional designer and facilitator who can create engaging learning experiences, role-based training programs, and performance support materials that drive adoption and proficiency.

Key Responsibilities

Instructional Design & Curriculum Development

  • Conduct training needs assessments and identify role-based learning requirements.
  • Design and develop curricula, learning paths, job aids, eLearning content, simulations, and performance support materials.
  • Apply adult learning and instructional design principles to create effective learning experiences.
  • Ensure training aligns with future-state business processes and ways of working.

Training Delivery & Enablement

  • Deliver instructor-led, virtual, and train-the-trainer programs.
  • Facilitate workshops and end-user learning sessions.
  • Partner with business SMEs to validate content and learning outcomes.
  • Manage learner participation, completion tracking, and reporting.

Readiness & Adoption

  • Assess learner readiness and proficiency.
  • Measure training effectiveness through assessments, feedback, and adoption metrics.
  • Support post-go-live reinforcement, coaching, and knowledge retention activities.
  • Continuously improve training programs based on learner feedback and business outcomes.

Collaboration & Continuous Improvement

  • Partner with Change Management, Product, Technology, and Operations teams to align training with release objectives.
  • Maintain training standards, templates, and learning repositories.
  • Contribute to lessons learned and continuous improvement activities across Guidewire releases.

Qualifications

  • Bachelor's degree or 7+ years of experience in Training, Learning & Development, Instructional Design, Change Management, or Organizational Effectiveness.
  • Proven experience designing and delivering training for large-scale technology implementations.
  • Strong instructional design experience, including curriculum development, eLearning, job aids, and performance support tools.
  • Strong facilitation, presentation, and stakeholder engagement skills.
  • Experience applying adult learning principles and instructional design methodologies.
  • Proficiency with Microsoft 365 tools, including Teams, SharePoint, PowerPoint, and Copilot.
  • Insurance industry and/or Guidewire experience preferred.

Preferred Skills

  • Experience leveraging AI tools (e.g., Microsoft Copilot, ChatGPT) to accelerate instructional design, content creation, training administration, and learning analytics.
  • Ability to translate complex business and technology concepts into clear, engaging learning experiences.
  • Experience creating role-based learning programs that improve user proficiency and adoption.

#LI-AB

#LI-Hybrid

US Work Authorization

US Work Authorization required. Markel does not provide visa sponsorship for this position, now or in the future.

Pay information:

The base salary offered for the successful candidate will be based on compensable factors such as job-relevant education, job-relevant experience, training, licensure,demonstratedcompetencies, geographic location, and other factors. The national average salary range for theTraining Lead - Guidewire is $88,000 - $110,000with 25% incentive.

Who we are:

Markel Group (NYSE - MKL) a fortune 500 company with over 60 offices in 20+ countries, is a holding company for insurance, reinsurance, specialist advisory and investment operations around the world.

We're all about people | We win together | We strive for better

We enjoy the everyday | We think further

What's in it for you:

In keeping with the values of the Markel Style, we strive to support our employees in living their lives to the fullest at home and at work.

  • We offer competitive benefit programs that help meet our diverse and changing environment as well as support our employees' needs at all stages of life.

  • All full-time employees have the option to select from multiple health, dental and vision insurance plan options and optional life, disability, and AD&D insurance.

  • We also offer a 401(k) with employer match contributions, an Employee Stock Purchase Plan, PTO, corporate holidays and floating holidays, parental leave.

Are you ready to play your part?

Choose 'Apply Now' to fill out our short application, so that we can find out more about you.

Caution: Employment scams

Markel is aware of employment-related scams where scammers will impersonate recruiters by sending fake job offers to those actively seeking employment in order to steal personal information. Frequently, the scammer will reach out to individuals who have posted their resume online. These "job offers" include convincing offer letters and frequently ask for confidential personal information. Therefore, for your safety, please note that:

  • All legitimate job postings with Markel will be posted on Markel Careers. No other URL should be trusted for job postings.

  • All legitimate communications with Markel recruiters will come from Markel.com email addresses.

We would also ask that you please report any job employment scams related to Markel to rarecruiting@markel.com.

Markel is an equal opportunity employer. We do not discriminate or allow discrimination on the basis of any protected characteristic. This includes race; color; sex; religion; creed; national origin or place of birth; ancestry; age; disability; affectional or sexual orientation; gender expression or identity; genetic information, sickle cell trait, or atypical hereditary cellular or blood trait; refusal to submit to genetic tests or make genetic test results available; medical condition; citizenship status; pregnancy, childbirth, or related medical conditions; marital status, civil union status, domestic partnership status, familial status, or family responsibilities; military or veteran status, including unfavorable discharge from military service; personal appearance, height, or weight; matriculation or political affiliation; expunged juvenile records; arrest and court records where prohibited by applicable law; status as a victim of domestic or sexual violence; public assistance status; order of protection status; status as a smoker or nonsmoker; membership or activity in local commissions; the use or nonuse of lawful products off employer premises during non-work hours; declining to attend meetings or participate in communications about religious or political matters; or any other classification protected by applicable law.

Should you require any accommodation through the application process, please send an e-mail to therarecruiting@markel.com.

No agencies please.

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