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Progressive Remote Jobs in Ohio, IL (NOW HIRING)

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Progressive Remote information

Does Progressive hire remote workers?

Progressive offers remote job opportunities for certain roles, particularly in customer service, claims, and sales. Remote positions typically require strong communication skills, computer proficiency, and sometimes specific certifications or training. Availability of remote work varies by position and location, so candidates should review current openings on the company's careers page.

What are Progressive Remote jobs?

Progressive Remote jobs refer to positions offered by Progressive Insurance that allow employees to work remotely, either full-time or part-time, from their homes or other locations outside of traditional office settings. These roles span various departments such as customer service, claims, sales, IT, and more. Progressive provides remote employees with the necessary technology and support to perform their duties effectively. Working remotely at Progressive offers flexibility, work-life balance, and opportunities for professional growth while still being part of a collaborative team.

How does working remotely for Progressive affect team communication and collaboration?

At Progressive, remote employees use a variety of digital tools to stay connected and collaborate effectively with their teams, including regular video meetings, chat platforms, and project management software. While remote work offers flexibility, it also means you’ll need to be proactive about communication and time management. Progressive fosters a supportive environment by encouraging open communication, providing training, and holding virtual team-building activities. You’ll often work cross-functionally with colleagues in different departments, so being comfortable with digital collaboration is key to success.

What is the difference between Progressive Remote vs Customer Support Specialist?

AspectProgressive RemoteCustomer Support Specialist
Required CredentialsBasic customer service skills, sometimes certifications in communication or support toolsCustomer service experience, communication skills, sometimes certifications in CRM software
Work EnvironmentRemote, flexible hours, home-basedRemote or on-site, customer interaction focus
Industry UsageInsurance, finance, tech companies offering remote rolesRetail, tech, service industries, often remote or call centers

Progressive Remote roles typically involve remote customer support positions requiring basic support skills and certifications, often in industries like insurance or finance. Customer Support Specialists also work remotely but may have more direct customer interaction and industry-specific experience. Both roles are remote-friendly but differ slightly in industry focus and required credentials.

Is it hard to get hired at Progressive?

Getting hired at Progressive can be competitive, as the company values relevant experience, strong communication skills, and a good fit for the role. The hiring process typically involves multiple interviews and assessments to evaluate candidates' qualifications and compatibility with the company's culture.

What are the key skills and qualifications needed to thrive as a Remote Customer Service Representative at Progressive, and why are they important?

To thrive as a Remote Customer Service Representative at Progressive, you need strong communication skills, problem-solving abilities, and typically a high school diploma or equivalent. Familiarity with customer relationship management (CRM) software and proficiency in navigating multiple computer systems are important technical requirements. Outstanding time management, self-motivation, and empathy allow you to deliver excellent service while working independently. These skills ensure efficient resolution of customer issues and contribute to high customer satisfaction in a remote environment.

How much does Progressive pay remote workers?

Progressive offers remote positions with pay rates that vary depending on the role, experience, and location. Salaries for remote jobs at Progressive typically range from around $40,000 to over $80,000 annually, with some roles offering additional benefits and performance incentives.

What is the easiest WFH job to get hired at?

Entry-level customer service representative or data entry roles are often considered among the easiest remote jobs to secure, as they typically require minimal experience and basic computer skills. These positions often involve standard software tools like email and spreadsheets and may offer flexible schedules, making them accessible for many job seekers.
Infographic showing various Progressive Remote job openings in Ohio, IL as of June 2026, with employment types broken down into 87% Full Time, 9% Part Time, and 4% Contract. Highlights an 90% Physical, 3% Hybrid, and 7% Remote job distribution.
Remote Investment Analyst - AI Trainer ($50-$60 per hour)

Remote Investment Analyst - AI Trainer ($50-$60 per hour)

Data Annotation

La Salle, IL • Remote

$50 - $60/hr

Full-time, Part-time, Contractor

This job post has expired today. Applications are no longer accepted.

Job description

DataAnnotation is committed to creating high-quality AI. Join our team to help train the next generation of AI while enjoying the flexibility of remote work and the freedom to set your own schedule. This role is designed to fit a variety of lifestyles — whether you’re looking to contribute part-time alongside a current position, pursue it full-time, or engage periodically as a flexible professional opportunity.

We're currently expanding into an exciting new area – teaching AI Assistant models to be a more useful tool for finance professionals. We're seeking experienced finance professionals with advanced degrees (MBA+) and professional experience to use their expertise to help shape how AI understands financial principles and decision-making.

We’re growing a team of finance experts, and as the team grows, so will your opportunities. In this role, you might:

  • Review and improve AI Assistant answers to questions about macro trends, corporate finance, and capital markets
  • Leverage your education and work experience to check the reasoning and accuracy of an AI Assistant's work
  • Push the models with complex, real-world scenarios and edge cases to see where their reasoning holds up – and where it doesn’t.
  • Share clear, structured feedback to help make each new version of the AI smarter and more reliable.

To succeed in this position, you should have expert-level financial reasoning and formal training in a finance-related discipline. A Master’s or PhD (completed or in progress) is strongly preferred. Relevant backgrounds include Financial Accounting, Investment Banking, Corporate Development, Wealth Management, and Insurance Planning.

Benefits:

  • This is a full-time or part-time REMOTE position
  • You’ll be able to choose which projects you want to work on
  • You can work on your own schedule
  • Projects are paid hourly starting at USD $50-$60 per hour, with bonuses on high-quality and high-volume work

Responsibilities:

  • Give AI chatbots diverse and complex problems and evaluate their outputs
  • Evaluate the quality produced by AI models for correctness and performance

Qualifications:

  • Fluency in English (native or bilingual level)
  • Detail-oriented
  • Proficient in financial analysis, financial modeling, data analysis, and other reasoning exercises related to finance management
  • A current, in progress, or completed Masters and/or PhD is is preferred but not required

Note: Payment is made via PayPal. We will never ask for any money from you. PayPal will handle any currency conversions from USD. This is an independent contract position.

Apply