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Rideshare Insurance Jobs in Chicago, IL (NOW HIRING)

RideShare RidenRoll App Drivers

Chicago, IL · On-site

$19.50 - $26.50/hr

Proof of vehicle insurance * Proof of vehicle inspection performed by the California Bureau of Automotive Repair and uploaded on the www.ridenroll.com Driver app when apply. * A driver profile ...

RideShare RidenRoll App Drivers

Chicago, IL · On-site

$19.50 - $26.50/hr

Proof of vehicle insurance * Proof of vehicle inspection performed by the California Bureau of Automotive Repair and uploaded on the www.ridenroll.com Driver app when apply. * A driver profile ...

Tool & Model Maker - P

Chicago, IL · On-site

$32 - $44/hr

Medical, dental, and vision insurance * 401(k) with company match and Employee Stock Ownership Plan ... Employee Assistance Program & Rideshare Program * Referral Bonus program What You'll Do As a Tool ...

Tool & Model Maker - P

Chicago, IL · On-site

$62K - $77K/yr

Medical, dental, and vision insurance * 401(k) with company match and Employee Stock Ownership Plan ... Employee Assistance Program & Rideshare Program * Referral Bonus program What You'll Do As a Tool ...

This is an active, outdoor position-not rideshare, delivery driving, or valet service. It is a good ... Medical, dental, and vision insurance 401(k) retirement plan with matching Paid holidays and ...

This is an active, outdoor position-not rideshare, delivery driving, or valet service. It is a good ... Medical, dental, and vision insurance 401(k) retirement plan with matching Paid holidays and ...

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Rideshare Insurance information

See Chicago, IL salary details

$9

$21

$50

How much do rideshare insurance jobs pay per hour?

As of Aug 9, 2026, the average hourly pay for rideshare insurance in Chicago, IL is $21.75, according to ZipRecruiter salary data. Most workers in this role earn between $14.62 and $20.58 per hour, depending on experience, location, and employer.

What is the difference between Rideshare Insurance vs Delivery Driver Insurance?

AspectRideshare InsuranceDelivery Driver Insurance
CredentialsStandard auto insurance, sometimes with rideshare endorsementsSimilar to rideshare, may require specific delivery endorsements
Work EnvironmentPassenger transportation via ride-hailing appsFood, package, or grocery delivery via apps
Industry UsageUsed by Uber, Lyft driversUsed by DoorDash, UberEats, Grubhub drivers
Search & ComparisonCommonly compared for coverage needs and costsOften compared to rideshare insurance for delivery-specific coverage

While both insurance types cater to gig economy drivers, rideshare insurance covers drivers transporting passengers, whereas delivery driver insurance focuses on food or package delivery. Understanding the differences ensures proper coverage for your specific work environment and needs.

What job categories do people searching Rideshare Insurance jobs in Chicago, IL look for? The top searched job categories for Rideshare Insurance jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Rideshare Insurance jobs? Cities near Chicago, IL with the most Rideshare Insurance job openings:
Infographic showing various Rideshare Insurance job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 74% Full Time, 20% Part Time, and 5% Contract. Highlights an 91% Physical, 1% Hybrid, and 8% Remote job distribution, with an average salary of $45,249 per year, or $21.8 per hour.

Claims Specialist II - Rideshare Commercial Auto - Attorney Represented Bodily Injury Claims Adju...

Liberty Mutual

Hoffman Estates, IL • On-site, Remote

Full-time

Re-posted 10 days ago


Liberty Mutual rating

8.9

Company rating: 8.9 out of 10

Based on 148 frontline employees who took The Breakroom Quiz

48th of 304 rated insurance


Job description

Description

The Claims Specialist works within a Claims Team, using the latest technology to manage a caseload of commercial rideshare, also known as Transportation Network Company (TNC), claims from initial investigation through resolution. The role handles claims involving complex injuries as well as claims involving high policy limits, attorney representation, litigation, uninsured/underinsured motorist coverage, and 3rd-party bodily injury. 

The Claims Specialist leverages expertise in coverage and liability, reserve analysis, damages assessment, negotiation strategy, and litigation management. This role partners with defense counsel, internal claims partners, and external vendors to ensure claims are managed accurately and efficiently, consistent with policy provisions, regulatory requirements, and company standards. 

You will be required to go into the office twice a month if you reside within 50 miles of one of the following offices: Boston, MA; Westborough, MA; Hoffman Estates, IL; Weatogue, CT; Indianapolis, IN; Plano, TX; Suwanee, GA; or Lake Oswego, OR; Las Vegas, NV; Chandler, AZ.  (Please note this policy is subject to change.) 

Responsibilities: 

  • Owns complex commercial rideshare/TNC claims from investigation through resolution, including determining coverage, liability, damages, and appropriate claim outcomes. 
  • Reviews commercial policy language, endorsements, exclusions, limits, conditions, and applicable coverage requirements to determine coverage. 
  • Investigates complex losses involving significant injuries, attorney representation, litigation, and UM/UIM coverages  
  • Evaluates the severity and complexity of injuries to assess medical exposure, future damages, and overall claim value. 
  • Establishes, documents, and updates accurate reserves throughout the life of the claim based on severity, exposure, venue, liability, policy limits, litigation status, and evolving facts. 
  • Determines amounts owed, evaluates settlement value, negotiates with plaintiff counsel and other parties, and authorizes settlements and payments within assigned authority; recommends or issues denials when appropriate. 
  • Manages attorney-represented and litigated claims, including developing resolution strategies and coordinating with defense counsel, Home Office Legal, Claims leadership, and other internal partners. 
  • Partners with defense counsel on pleadings, discovery plans, litigation plans, case evaluations, mediation preparation, deposition strategy, trial preparation, and settlement negotiations 
  • Reviews pleadings, discovery, depositions, expert reports, medical records, suit documentation, investigation materials, and claim files to determine appropriate actions and litigation strategy. 
  • Prepares claims for mediation, deposition, and potential trial by analyzing liability, coverage, damages, documentation, venue considerations, and settlement authority. 
  • Performs other duties as assigned, including participation in special projects, training, guidance, and mentorship to staff. 
  • Experience handling commercial/Transportation Network Company (TNC) claims and/or larger policies.
  • Experience with high-exposure claims involving severe injury, soft tissue, fractured bones, catastrophic loss, or fatalities.
  • Prior handling of attorney-represented and/or litigated claims in a commercial or specialty lines environment.
  • Experience preparing claims for mediation, deposition, trial, or other litigation milestones.
  • Background in settlement negotiation with attorneys and/or plaintiff counsel and coordination with defense counsel.
  • Experience handling complex policy interpretation and coverage analysis on large commercial accounts.
  • Familiarity with time limit demands, discovery, legal expense management, and litigation strategy.
  • Experience managing high-limit claims with detailed reserve and exposure analysis.
  • Knowledge of multi-state claim handling and jurisdictional issues.
  • Experience working in a high-performance claims environment where quality, precision, and responsiveness are expected
Qualifications
  • BS/BA degree or equivalent work experience.
  • Minimum of 2 years' experience in claims adjustment, general insurance or formal claims training.
  • Required to obtain and maintain all applicable licenses.
  • Continuing education courses leading to industry certifications preferred (e.g., AEI, IIA, CPCU).
  • Knowledge of claims investigation techniques, medical terminology and legal aspects of claims.
About Us

Pay Philosophy: The typical starting salary range for this role is determined by a number of factors including skills, experience, education, certifications and location. The full salary range for this role reflects the competitive labor market value for all employees in these positions across the national market and provides an opportunity to progress as employees grow and develop within the role. Some roles at Liberty Mutual have a corresponding compensation plan which may include commission and/or bonus earnings at rates that vary based on multiple factors set forth in the compensation plan for the role.At Liberty Mutual, our goal is to create a workplace where everyone feels valued, supported, and can thrive. We build an environment that welcomes a wide range of perspectives and experiences, with inclusion embedded in every aspect of our culture and reflected in everyday interactions. This comes to life through comprehensive benefits, workplace flexibility, professional development opportunities, and a host of opportunities provided through our Employee Resource Groups. Each employee plays a role in creating our inclusive culture, which supports every individual to do their best work. Together, we cultivate a community where everyone can make a meaningful impact for our business, our customers, and the communities we serve. We value your hard work, integrity and commitment to make things better, and we put people first by offering you benefits that support your life and well-being. To learn more about our benefit offerings please visit: https://www.libertymutualgroup.com/about-lm/careers/benefitsLiberty Mutual is an equal opportunity employer. We will not tolerate discrimination on the basis of race, color, national origin, sex, sexual orientation, gender identity, religion, age, disability, veteran's status, pregnancy, genetic information or on any basis prohibited by federal, state or local law.Fair Chance Notices

  • California
  • Los Angeles Incorporated
  • Los Angeles Unincorporated
  • Philadelphia
  • San Francisco
Employment Type: FULL_TIME

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About Liberty Mutual

Sourced by ZipRecruiter

Since 1912, we've grown into the fifth largest global property and casualty insurer based on 2022 gross written premium. We also rank 86 on the Fortune 100 list of largest corporations in the US based on 2022 revenue. ​At Liberty Mutual Insurance we work hard every day to support our customers and our people, so they can protect their families, build their businesses and invest in their futures. We are headquartered in Boston, but our people, our customers and our reach span the globe. So to better serve our global customers and employees, we are organized into three business units.

Industry

Insurance services

Company size

10,000+ Employees

Headquarters location

Boston, MA, US

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